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1. Compound ID: 271
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-2)-b-D-Rhap-(1-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: D-rhamnan
Compound class: O-polysaccharide, CPS
Contained glycoepitopes: IEDB_1394181,IEDB_145006,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 71
Fedonenko YP, Zatonsky GV, Konnova SA, Zdorovenko EL, Ignatov VV "Structure of the O-specific polysaccharide of the lipopolysaccharide of Azospirillum brasilense Sp245" -
Carbohydrate Research 337(9) (2002) 869-872
An O-specific polysaccharide was isolated from the lipopolysaccharide of a plant-growth-promoting bacterium Azospirillum brasilense Sp245 and studied by sugar analyses along with one- and two-dimensional 1H and 13C NMR spectroscopy, including NOESY. The polysaccharide was found to be a new rhamnan with a pentasaccharide repeating unit having the following structure: →2)-β-D-Rhap-(1→3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→2)-α-D-Rhap-(1→
Lipopolysaccharide, O-antigen, Bacterial polysaccharide, Asymbiotic diazotroph, Azospirillum brasilense
NCBI PubMed ID: 11996841Publication DOI: 10.1016/S0008-6215(02)00061-7Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Prospekt Entuziastov 13, 410015 Saratov, Russia, bN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Prospekt 47, Moscow, Russia
Methods: NMR-2D, methylation, NMR, sugar analysis
- Article ID: 1610
Fedonenko YP, Borisov IV, Konnova ON, Zdorovenko EL, Katsy SA, Konnova SA, Ignatov VV "Determination of the structure of the repeated unit of the Azospirillum brasilense SR75 O-specific polysaccharide and homology of the lps loci in the plasmids of Azospirillum brasilense strains SR75 and Sp245" -
Mikrobiologiia = Microbiology [Russian] 74(5) (2005) 626-632
The structural identity of the repeated unit in O-specific polysaccharides (OPSs) present in the outer membrane of strain SR75 of the bacterium Azospirillum brasilense, isolated from wheat rhizosphere in Saratov oblast, and the OPSs of previously studied A. brasilense strain Sp245, isolated from surface-sterilized wheat roots in Brazil, has been demonstrated. Plasmid profiles, DNA restriction, and hybridization assays suggested that A. brasilense strains SR75 and Sp245 have different genomic structures. It was shown that homologous lps loci of both strains was localized in their plasmid DNA. This fact allows us to state that, despite their different origin, the development of the strains studied was convergent. Presumably, the habitation of these bacteria in similar ecological niches influenced this process in many respects
LPS, structure, DNA, strain, structural, polysaccharide, polysaccharides, determination, bacteria, O-specific, O-specific polysaccharide, Azospirillum brasilense, plasmid, O-specific polysaccharides, homology, membrane, outer membrane, root, assay, origin, Plasmids, homologous, development, Azospirillum, P, profile, restriction, ecological, rhizosphere, wheat
NCBI PubMed ID: 16315981Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Institutions: Institute of biochemistry and Physiology of Plants and Microorganisms RAS, Saratov
Methods: methylation, NMR, sugar analysis
- Article ID: 3743
Molinaro A, Newman M, Lanzetta R, Parrilli M "The structures of lipopolysaccharides from plant-associated Gram-negative bacteria" -
European Journal of Organic Chemistry 2009(34) (2009) 5887-5896
Gram-negative bacterial lipopolysaccharides (LPSs) have multiple roles in plant-microbe interactions. LPSs contribute to the low permeabilities of bacterial outer membranes, which act as barriers to protect bacteria from plant-derived antimicrobial substances. Conversely, perception of LPSs by plant cells can lead to the triggering of defence responses or to the priming of the plant to respond more rapidly and/or to a greater degree to subsequent pathogen challenge. LPSs are thus key molecules in the interactions between bacteria and plants, either in symbiosis or pathogenesis. Since LPSs are glycoconjugates genetically and chemically consisting of three different molecular regions, their detailed structure elucidation is a very topical and major scientific task for chemists, and is achieved by a combination of state-of-art chemical and spectroscopic techniques. Knowledge of LPSs' chemical structures is an important prerequisite for any further understanding of the biological processes in plant-microbe interactions. Moreover, the LPSs from Gram-negative bacteria - especially those originating from plant-associated bacteria - are a great source of novel monosaccharides with unusual and occasionally astounding chemical structures, never found in the eukaryotic world. This review presents the structures of LPSs from plant-associated bacteria isolated and identified from 2001 onwards.
lipopolysaccharides, structure elucidation, glycolipids, innate immunity, immunochemistry, plant-associated bacteria
Publication DOI: 10.1002/ejoc.200900682Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: molinaro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli “Federico II”, via Cinthia 4, 80126 Napoli, Italy, Fax: +39-081-674393, Faculty of Life Sciences, Department of Plant Biology & Biotechnology, University of Copenhagen, 1871 Frederiksberg, Denmark
- Article ID: 3821
Boiko AS, Smol'kina ON, Fedonenko YP, Zdorovenko EL, Kachala VV, Konnova SA, Ignatov VV "O-polysaccharide structure in serogroup I Azospirilla" -
Mikrobiologiia = Microbiology [Russian] 79(2) (2010) 197-205
Lipopolysaccharides (LPS) and O-specific polysaccharides (OPS) were obtained from the outermembrane of four Azospirillum strains previously assigned to serogroup I based on the serological affinityrevealed by the antibodies (AB) to the LPS of A. brasilense Sp245. Investigation, including determination ofmonosaccharide composition, methylation analysis, and one- and two-dimensional NMR spectroscopy, wascarried out to determine the OPS structure. The OPSs of A. brasilense Sp107 and S27 and of A. lipoferumRG20a were found to have an identical structure of repeating units represented by a linear penta-D-rhamnan,as was previously described for the OPSs of A. brasilense Sp245 and SR75. The OPS of A. brasilense SR15was found to consist of tetrasaccharide repeating units of the following structure: frame0 2)--D-Rhap-(1 frame1 2)--D-Rhap-(1 frame2 3)--D-Rhap-(1 frame3 2)--D-Rhap-(1 frame4. An opine compound, N-(1-carboxyethyl)-orni-thine, closely associated with the LPS of A. brasilense SR15, was identified in azospirilla for the first time. Thepresence of a 6-deoxisugar (D-rhamnose) in the OPS structure was shown to be the chemical basis of the sero-logical similarity and the reason for classification of these strains within the serogroup I.
Lipopolysaccharide, serological characterization, Azospirillum, structure of O-specific polysaccharides
Publication DOI: 10.1134/S0026261710020116Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: alevtinab10@mail.ru
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Saratov, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, SDS-PAGE, EIA, Smith degradation, composition analysis, NMR-1D, serological methods
- Article ID: 3843
Fedonenko YP, Katsy EI, Petrova LP, Boyko AS, Zdorovenko EL, Kachala VV, Shashkov AS, Knirel YA "The structure of the O-specific polysaccharide from a mutant of nitrogen-fixing rhizobacterium Azospirillum brasilense Sp245 with an altered plasmid content" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 36(2) (2010) 219-223
The rhizobacteria Azospirillum brasilense Sp245 produce immunochemically different lipopolysaccharides LPSI and LPSII, both containing identical pentasaccharides built from Drhamnose residues as the repeating units of Ospecific polysaccharides (OPS). In this study, we report the structure of the OPS from A. brasilense LPSI-LPSII- mutant Sp245.5, which spontaneously lost the p85 and p120 plasmids upon the formation of a new 300MDa megaplasmid after the longterm storage of the bacteria in a rich medium. The repeating unit of the OPS of A. brasilense Sp245.5 appeared to be a disaccharide consisting of residues of Nacetyl-D-galactosamine and Nacetyl-D-mannosaminuronic acid: (formula, see text).
Azospirillum brasilense, O-Specific polysaccharide structure, plasmid rearrangements
NCBI PubMed ID: 20531482Publication DOI: 10.1134/S1068162010020111Journal NLM ID: 7804941Publisher: Moskva: Nauka
Correspondence: fedonenko@ibppm.sgu.ru
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, pr. Entuziastov 13, Saratov, 410049 Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, acid hydrolysis, composition analysis
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4723
Sigida EN, Fedorova EE, Zdorovenko EL, Burygin GL, Konnova SA, Ignatov VV "Characterization of the lipopolysaccharides of serogroup II Azospirillum strains" -
Mikrobiologiia = Microbiology [Russian] 83(4) (2014) 326-334
Lipopolysaccharides of six Azospirillum brasilense strains (SR50, SR80, SR88, SR109, SR111, SR115) and A. lipoferum SR 42 isolated from the rhizosphere of cereal plants of Saratov oblast, Russia and referred to serogroup II by serological analysis were studied. In the lipid A fatty acid composition, the lipopolysaccharides under study were similar to those of other Azospirillum strains and were characterized by a predominance of 3-hydroxytetradecanoic, 3-hydroxyhexadecanoic, and octadecenoic acids. Monosaccharide analysis of the O-specific polysaccharides (including determination of the absolute configurations, methylation analysis, and one- and two-dimensional NMR spectroscopy) revealed the presence of two types of repeating units in varying ratios. A high degree of serological similarity between the strains under study was shown to result from the presence of repeating units with identical structure of their O antigens.
lipopolysaccharides, Azospirillum, structure of the Ospecific polysaccharide, serological investigation
Publication DOI: 10.1134/S0026261714040158Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: Sigida EN
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Saratov, Russia, Chernyshevsky Saratov State University, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, ELISA, GLC, mild acid hydrolysis, Western blotting, serological methods, GPC
- Article ID: 4843
Fedonenko YP, Sigida EN, Konnova SA, Ignatov VV "Structure and serology of O-antigens of nitrogen-fixing rhizobacteria of the genus Azospirillum" -
Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 64(5) (2015) 1024-1031
The review presents a discussion of the published data of 2002 to 2014 dealing with structural studies of O-specific polysaccharides, representatives of the Azospirillum diazotrophic rhizobacteria, summarizing the results of a series of authors? studies. Some general structures incorporated in O-specific polysaccharides responsible for classification of bacterial cultures into serogroups on the basis of immunochemical studies were characterized. The structures of O-specific polysaccharides of seven azospirillum strains identical to those of previously studied strains are presented in this review for the first time.
lipopolysaccharides, O-specific polysaccharides, Structures, Azospirillum, O-antigenic determinants
Publication DOI: 10.1007/s11172-015-0971-xJournal NLM ID: 100912060Publisher: New York: Consultants Bureau
Correspondence: si_elena@mail.ru
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms Russian Academy of Sciences, 13 prosp. Entuziastov, 410049 Saratov, Russian Federation
- Article ID: 5430
Evstigneeva SS, Sigida EN, Fedonenko YP, Konnova SA, Ignatov VV "Structural Properties of Capsular and O-Specific Polysaccharides of Azospirillum brasilense SP245 under Varying Cultivation Conditions" -
Mikrobiologiia = Microbiology [Russian] 85(6) (2016) 664-671
Effect of the carbon source in the culture medium and of the growth phase on the composition and structure of the capsular polysaccharides (CPSs) and lipopolysaccharides (LPSs) of the bacterium Azospirillum brasilense Sp245 was studied. Growth with fructose resulted in an increased carbohydrate content in the CPSs, while long-term cultivation resulted in an increased content of phosphorus in both CPSs and LPSs. The LPSs produced on the medium with fructose (regardless of the cultivation duration) and the LPSs of the bacteria grown with sodium malate until the stationary phase were characterized by higher levels of unsaturated fatty acids than the LPSs of the bacteria grown with sodium malate to the late exponential phase. The structures of the polysaccharides from the isolated glycopolymers were established using monosaccharide analysis, including determination of the absolute configurations and 1D and 2D NMR spectroscopy. This study is the first to report that the CPS of A. brasilense Sp245 grown with sodium malate to the end of the exponential phase is structurally identical to the O-polysaccharide from the LPS of this bacterium and that the LPS and CPS of A. brasilense Sp245 grown with fructose contain an additional homoglucan of the following structure: [→3)-α-D-Glcp-(1→]n.
Lipopolysaccharide, capsular polysaccharide, Azospirillum brasilense, Azospirillum, cultivation conditions
Publication DOI: 10.1134/S0026261716060096Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: Stels20295@yandex.ru
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russia, Chernyshevskii National Research Saratov State University, Saratov, Russia
Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, GLC-MS, SDS-PAGE, GLC, composition analysis
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
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2. Compound ID: 825
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b-D-Xylp-(1-2)-+
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-2)-a-D-Rhap-(1-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-
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b-D-Xylp-(1-4)-+ |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_114701,IEDB_1394181,IEDB_144831,IEDB_145005,IEDB_145006,IEDB_145010,IEDB_167188,IEDB_174332
The structure is contained in the following publication(s):
- Article ID: 226
Winn AM, Wilkinson SG "Structures of the O4 and O18 antigens of Stenotrophomonas maltophilia: a case of enantiomeric repeating units" -
Carbohydrate Research 330(2) (2001) 215-221
The O-specific side-chain polymers of lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroups O4 and O18 are both xylosylated rhamnans. In the O4 polymer, both sugar components are the D isomers, whereas the O18 polymer contains only the L isomers. By means of NMR spectroscopy, methylation analysis and Smith degradation, the repeating unit of the O4 polymer was identified as a doubly-branched pentasaccharide of the structure shown below. The O18 polymer is based on the enantiomeric pentasaccharide, but the xylosyl substituent at the 4-position is apparently absent from some units. The polymers closely resemble the O antigens found in Xanthomonas campestris pathovars.
Lipopolysaccharide, O antigens, Stenotrophomonas maltophilia, Xanthomonas
NCBI PubMed ID: 11217974Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: s.g.wilkinson@chem.hull.ac.uk
Institutions: Department of Chemistry, Faculty of Science and the Environment, University of Hull, Hull HU6 7RX, UK
Methods: methylation, NMR, Smith degradation
- Article ID: 1777
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1839
Knirel YA, Zdorovenko GM, Shashkov AS, Zakharova IY, Kochetkov NK "Antigenic polysaccharides of bacteria. 19. Structure of O-specific polysaccharide chain of Alcaligenes faecalis lipopolysaccharide" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12 (1986) 1530-1539
On mild acid hydrolysis of Alcaligenes faecalis lipopolysaccharide, the O-specific polysaccharide containing D-rhamnose and D-xylose in the 3:2 ratio was obtained. Solvolysis of the polysaccharide with hydrogen fluoride in methanol resulted in methyl glycoside of a branched tetrasaccharide including three rhamnose and one xylose residues. Smith degradation of the polysaccharide led to the glycoside of disaccharide composed of two rhamnose residues and glycerol. On the basis of identification of the oligosaccharide fragments, methylation, 1H and 13C NMR analysis (including nuclear Overhauser effect data), it was established that the polysaccharide linear chain is a rhamnan, both xylose residues being attached to one of the rhamnose residues as two branches. The repeating unit of the polysaccharide has the following structure: (Formula: see text).
NCBI PubMed ID: 2432903Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR, HF solvolysis, Smith degradation
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 6142
Shimoyama A, Di Lorenzo F, Yamaura H, Mizote K, Palmigiano A, Pither MD, Speciale I, Uto T, Masui S, Sturiale L, Garozzo D, Hosomi K, Shibata N, Kabayama K, Fujimoto Y, Silipo A, Kunisawa J, Kiyono H, Molinaro A, Fukase K "Lipopolysaccharide from Gut-Associated Lymphoid-Tissue-Resident Alcaligenes faecalis: Complete Structure Determination and Chemical Synthesis of Its Lipid A" -
Angewandte Chemie, International Edition 60(18) (2021) 10023-10031
Alcaligenes faecalis is the predominant Gram-negative bacterium inhabiting gut-associated lymphoid tissues, Peyer's patches. We previously reported that an A. faecalis lipopolysaccharide (LPS) acted as a weak agonist for Toll-like receptor 4 (TLR4)/myeloid differentiation factor-2 (MD-2) receptor as well as a potent inducer of IgA without excessive inflammation, thus suggesting that A. faecalis LPS might be used as a safe adjuvant. In this study, we characterized the structure of both the lipooligosaccharide (LOS) and LPS from A. faecalis. We synthesized three lipid A molecules with different degrees of acylation by an efficient route involving the simultaneous introduction of 1- and 4'-phosphates. Hexaacylated A. faecalis lipid A showed moderate agonistic activity towards TLR4-mediated signaling and the ability to elicit a discrete interleukin-6 release in human cell lines and mice. It was thus found to be the active principle of the LOS/LPS and a promising vaccine adjuvant candidate.
lipopolysaccharides, lipid A, Oligosaccharides, vaccines, glycolipids, Alcaligenes
NCBI PubMed ID: 33522128Publication DOI: 10.1002/anie.202012374Journal NLM ID: 0370543Publisher: Weinheim: Wiley-VCH
Correspondence: molinaro@unina.it; Koichi Fukase
Institutions: Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126, Naples, Italy, Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan, Project Research Center for Fundamental Sciences, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan, Department of Chemical Sciences and Task Force on Microbiome Studies, University of Naples Federico II, Via Cinthia 4, 80126, Naples, Italy, CNR, Institute for Polymers, Composites and Biomaterials IPCB, Via P. Gaifami 18, 95126, Catania, Italy, Laboratory of Vaccine Materials, Center for Vaccine and Adjuvant Research, and Laboratory of Gut Environmental System, National Institutes of Biomedical Innovation, Health and Nutrition, Osaka, 567-0085, Japan, Faculty of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo, 169-8555, Japan, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa, 223-8522, Japan, International Research and Development Center for Mucosal Vaccines, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku, Tokyo, 108-8639, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, GLC-MS, de-O-acylation, SDS-PAGE, TLC, 31P NMR, chemical synthesis, MALDI-TOF MS, composition analysis, HPLC, de-N-acylation
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3. Compound ID: 827
Structure type: polymer chemical repeating unit
Trivial name: common antigen, common polysaccharide antigen, A band polysaccharide, D-rhamnan, repeat unit of the lipopolysaccharide side-chain, A-band polysaccharide (A-PS), A-band polysaccharide
Compound class: O-polysaccharide, O-antigen, LPS, Enterobacterial common antigen, enterobacterial common antigen, CPA
Contained glycoepitopes: IEDB_1394181,IEDB_144831,IEDB_145005,IEDB_145006,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 226
Winn AM, Wilkinson SG "Structures of the O4 and O18 antigens of Stenotrophomonas maltophilia: a case of enantiomeric repeating units" -
Carbohydrate Research 330(2) (2001) 215-221
The O-specific side-chain polymers of lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroups O4 and O18 are both xylosylated rhamnans. In the O4 polymer, both sugar components are the D isomers, whereas the O18 polymer contains only the L isomers. By means of NMR spectroscopy, methylation analysis and Smith degradation, the repeating unit of the O4 polymer was identified as a doubly-branched pentasaccharide of the structure shown below. The O18 polymer is based on the enantiomeric pentasaccharide, but the xylosyl substituent at the 4-position is apparently absent from some units. The polymers closely resemble the O antigens found in Xanthomonas campestris pathovars.
Lipopolysaccharide, O antigens, Stenotrophomonas maltophilia, Xanthomonas
NCBI PubMed ID: 11217974Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: s.g.wilkinson@chem.hull.ac.uk
Institutions: Department of Chemistry, Faculty of Science and the Environment, University of Hull, Hull HU6 7RX, UK
Methods: methylation, NMR, Smith degradation
- Article ID: 355
Rahim R, Burrows LL, Monteiro MA, Perry MB, Lam JS "Involvement of the rml locus in core oligosaccharide and O polysaccharide assembly in Pseudomonas aeruginosa" -
Microbiology (2000) 2803-2814
L-Rhamnose (L-Rha) is a component of the lipopolysaccharide (LPS) core, several O antigen polysaccharides, and the cell surface surfactant rhamnolipid of Pseudomonas aeruginosa. In this study, four contiguous genes (rmlBDAC) responsible for the synthesis of dTDP-L-Rha in P. aeruginosa have been cloned and characterized. Non-polar chromosomal rmlC mutants were generated in P. aeruginosa strains PAO1 (serotype O5) and PAK (serotype O6) and LPS extracted from the mutants was analysed by SDS-PAGE and Western immunoblotting. rmlC mutants of both serotype O5 and serotype O6 synthesized a truncated core region which was unable to act as an attachment point for either A-band or B-band O antigen. A rmd rmlC PAO1 double mutant (deficient in biosynthesis of both D-Rha and L-Rha) was constructed to facilitate structural analysis of the mutant core region. This strain has an incomplete core oligosaccharide region and does not produce A-band O antigen. These results provide the genetic and structural evidence that L-Rha is the receptor on the P. aeruginosa LPS core for the attachment of O polysaccharides. This is the first report of a genetically defined mutation that affects the synthesis of a single sugar in the core oligosaccharide region of P. aeruginosa LPS, and provides further insight into the mechanisms of LPS biosynthesis and assembly in this bacterium.
Lipopolysaccharide, Pseudomonas aeruginosa, L-rhamnose, rml, rmd
NCBI PubMed ID: 11065359Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: jlam@uoguelph.ca
Institutions: Department of Microbiology, University of Guelph, Guelph, Ontario, Canada, N1G 2W1, Canadian Bacterial Diseases Network, Networks of Centers of Excellence, Heritage Medical Research Building, Hospital Drive, Calgary, Alberta, Canada T2N 4N1, Center for Infection and Biomaterials Research, NU13-143, Toronto General Hospital, Toronto, Ontario, Canada M5G 2C4, Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A OR6
Methods: genetic methods
- Article ID: 421
Winn AM, Wilkinson SG "The O7 antigen of Stenotrophomonas maltophilia is a linear D-rhamnan with a trisaccharide repeating unit that is also present in polymers from some Pseudomonas and Burkholderia species" -
FEMS Microbiology Letters 166(1) (1998) 57-61
The O antigen polymer recovered from the reference strain for Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia serogroup O7, after mild acid hydrolysis of the lipopolysaccharide, was constructed from D-rhamnose. By means of chemical degradations and NMR studies, the repeating unit of the polymer was shown to be a linear trisaccharide with the structure →2)-α-D-Rhap-(1→3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→. The same repeating unit is present in the common antigen of Pseudomonas aeruginosa and in O antigens from some pathovars of Pseudomonas syringae and a strain of Burkholderia (Pseudomonas) cepacia
Lipopolysaccharide, O antigen, Stenotrophomonas maltophilia, d-Rhamnan
NCBI PubMed ID: 9741084Journal NLM ID: 7705721Publisher: Blackwell Publishing
Correspondence: S.G.Wilkinson@chem.hull.ac.uk
Institutions: Department of Chemistry, University of Hull, Hull HU6 7RX, UK
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, FAB-MS, HPAEC, Smith degradation
- Article ID: 763
Cérantola S, Montrozier H "Structural elucidation of two polysaccharides present in the lipopolysaccharide of a clinical isolate of Burkholderia cepacia" -
European Journal of Biochemistry 246(2) (1997) 360-366
Based on the sugar composition, methylation analyses and Smith degradation, supported by NMR spectroscopic analyses and fast-atom-bombardment MS experiments, the lipopolysaccharide produced by a clinical isolate of Burkholderia cepacia was shown to contain two distinct polymers, both with linear trisaccharide repeating units; a major, containing D-rhamnose and D-galactose residues (2:1) with the structure →3)-α-D-Rhap(1→3)-α-D-Rhap(1→4)-α-D-Galp(1→ (major), and a minor repeating unit, constituted by D-rhamnosyl residues, with the structure →3)-α-D-Rhap(1→3)-α-D-Rhap(1→2)-α-D-Rhap(1→ (minor).
Lipopolysaccharide, LPS, clinical, isolate, structural, polysaccharide, Burkholderia, Burkholderia cepacia, polysaccharides, elucidation, cystic fibrosis, D-rhamnose, fast-atom-bombardment MS
NCBI PubMed ID: 9208925Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Institut de Pharmacologie et de Biologie Structurale du CNRS, Toulouse, France
Methods: NMR-2D, methylation, NMR, sugar analysis, Smith degradation, partial depolymerization
- Article ID: 912
Lam JS, Rocchetta HL, Burrows LL "Glycosyltransferases of Pseudomonas aeruginosa that assemble the O antigens of A band and B band lipopolysaccharide" -
Journal of Endotoxin Research (1999) 96-101
Pseudomonas aeruginosa produces two forms of lipopolysaccharide (LPS) designated A band and B band. The O-polysaccharide region of A band is a conserved D-rhamnan polymer arranged alfa1-2,alfa1-3,alfa1-3, while B band is serotype-specific with differences in the O-antigenic region dividing P. aeruginosa into 20 stereotypes. The B band O-antigen unit of serotype O5 is [-4)bDMan(2NAc3N)A(1-4)bDMan(2NAc3NAc)A(1-3)aDFuc2NAc]. The glycosidic structure of LPS molecules specified by the action of dedicated glycosyltransferases. The wbp clusters of A band and B band (serotype O5) were each found to contain three genes coding for putative glycosyltransferases: wbpX, wbpY, wbpZ, and wbpH, wbpJ, wbpL, respectively. To examine the role of these potential transferases in LPS assembly, chromosomal mutaions were generated within all 6 genes. LPS analysis reveals that wbpX, wbpY and wbpZ mutants express and A-B+ phenotype, while wbpH and wbpJ metanst are A+B-. Interstingly, mutations in wbpL, and Escherichia coli wecA homologue, abrogates both A band and B band LPS synthesis, Based on amino acid homologies, O-polysaccharide structures and LPS phenotypes of transferase mutants, we propose and assembly scheme for these two LPS molecules.
Lipopolysaccharide, biosynthesis, genetic, antigen, characterization, O-antigen, B-band, O antigen, Pseudomonas, Pseudomonas aeruginosa, antigens, O antigens, O-antigens, glycosyltransferases, biochemical, review, glycosyltransferase, operon, A-band
Publication DOI: 10.1177/09680519990050011001Journal NLM ID: 9433350Publisher: Maney Publishing
Correspondence: jlam@uoguelph.ca
Institutions: Canadian Bacterial Diseases Network, Department of Microbiology, University of Gueoph, Gueoph, Ontario, Canada
- Article ID: 1071
Ovod V, Rudolph K, Knirel YA, Krohn K "Immunochemical characterization of O polysaccharides composing the a-D-rhamnose backbone of lipopolysaccharide of Pseudomonas syringae and classification of bacteria into serogroups O1 and O2 with monoclonal antibodies" -
Journal of Bacteriology 178 (1996) 6459-6465
Murine monoclonal antibodies (MAbs) reacting with Pseudomonas syringae lipopolysaccharide (LPS) O polysaccharides (OPS) composed of tetra- and tri-α-D-rhamnose repeats in the backbone [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1-2)D-Rha(α1] and [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1] were generated and used for immunochemical analysis and for serological classification of the bacteria. A total of 195 of 358 P. syringae strains tested representing 21 pathovars were shown to share a common epitope, 1a, and were classified into serogroup O1. All strains with pathovars aptata, glycinea, japonica, phaseolicola, and pisi, most of the strains with pathovars atrofaciens and striafaciens, and half of the strains with pathovar syringae were classified into serotypes O1a', O1b, O1c, and O1d within serogroup O1. Serogroup-specific epitope 1a was inferred to be related to the (α1-2)D-Rha(α1-3) site of the OPS backbone. The serotype-specific epitopes 1b, 1c, 1d, and 1a' were inferred as relating to the immunodominant lateral (α1-3)D-Rha, (β1-4)D-GlcNAc, and (α1-4)D-Fuc substituents and backbone-located site (α1-3)D-Rha(α1-2), respectively, of OPSs that share the common tetra-D-rhamnose repeats in the backbone. A total of 7.3% of the strains studied, all with pathovars morsprunorum and lapsa, were classified as serotypes O2a and O2d within serogroup 02. Serotype-specific epitope 2a was inferred as being related to the backbone-located site D-Rha(α1-3)D-Rha and epitope 2d to the immunodominant lateral (α1-4)D-Fuc residue of OPS consisting of tri-D-rhamnose repeats in the backbone. Epitope 2d alternated with 2a within the same LPS molecule and did not cross-react with epitope 1d. Serotypes O2a and O2d were observed in some strains correlating with the coexpression of the two chemotypes of OPS by the same strain. The serogroup O1-specific MAb Ps1a reacted weakly but definitely with all strains from serogroup 02. We propose serological formulas for serogroups O1 and 02 as well as for individual strains within these serogroups.
Lipopolysaccharide, LPS, characterization, polysaccharide, polysaccharides, Pseudomonas, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, serogroup, backbone, immunochemical, Pseudomonas syringae, classification, D-rhamnose
NCBI PubMed ID: 8932301Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Ltvlov@uta.fi
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Tampere, Finland, Department of Microbiology and Immunology, University of Kiev, Kiev, Ukraine, Institut fur Pflanzenpathologie und Pflanzenschutz der Georg-August-Universitat, Gottingen, Germany
Methods: serological methods
- Article ID: 1073
Ovod V, Knirel Y, Krohn K "Demonstration of the immunochemical diversity of O-chains of lipopolysaccharide of Pseudomonas syringae and inferring of the serogroup- and serotype-specific epitopes with monoclonal antibodies" -
Proceedings of International Conference on Pseudomonas syringae Pathovars and Related Pathogens (5th : 1995 : Berlin, Germany) (1997) Vol. 9, 532-537
Using serogroup- and serotyppe-specific murine monoclonal antibodies (MAbs) to Pseudomonas syringae lipopolysacharide (LPS) O-polysaccharides (OPS) (=O chains) with elucidated primary chemical structure of the O-repeating units, a rather high diversity of the OPS-related epitopes was demonstrated and most of them were inferred. The immunogenic properties of the O-serogroup- and O-serotype-specific epitopes were shown to depend on the nature and the number of sugar residues in the O-repeat as well as on the arrangement of the monosaccharides and the mode of linkages between them.
Lipopolysaccharide, LPS, structure, strain, Pseudomonas, chain, group, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, epitopes, O-polysaccharide, serogroup, immunochemical, O-chain, pathogen, pathogens, pathovar, Pseudomonas syringae, classification, diversity, serotype-specific
Publisher: Kluwer Academic Publishers, The Netherlands
Correspondence: knirel@ioc.ac.ru
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead DE, Vivian A, von Kietzell J
Institutions: Institute of Medical Technology, University of Tampere, Tampere, Finland, N.D. Zelinsy Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1074
Ovod V, Knirel YA, Samson R, Krohn K "Immunochemical characterization and taxonomic evaluation of the O polysaccharides of the lipopolysaccharides of Pseudomonas syringae serogroup O1 strains" -
Journal of Bacteriology 181(22) (1999) 6937-6947
The O polysaccharide (OPS) of the lipopolysaccharide (LPS) of Pseudomonas syringae pv. atrofaciens IMV 7836 and some other strains that are classified in serogroup O1 was shown to be a novel linear α-D-rhamnan with the tetrasaccharide O repeat →3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→2)-α-D-Rhap-(1→ (chemotype 1A). The same α-D-rhamnan serves as the backbone in branched OPSs with lateral (α1→3)-linked D-Rhap, (β1→4)-linked D-GlcpNAc, and (α1→4)-linked D-Fucf residues (chemotypes 1B, 1C, and 1D, respectively). Strains of chemotype 1C demonstrated variations resulting in a decrease of the degree of substitution of the backbone 1A with the lateral D-GlcNAc residue (chemotype 1C-1A), which may be described as branched regular <→ branched irregular → linear OPS structure alterations (1C <→ 1C-1A → 1A). Based on serological data, chemotype 1D was suggested to undergo a 1D <→ 1D-1A alteration, whereas chemotype 1B showed no alteration. A number of OPS backbone-specific monoclonal antibodies (MAbs), Ps(1-2)a, Ps(1-2)a(1), Ps1a, Ps1a(1), and Ps1a(2), as well as MAbs Ps1b, Ps1c, Ps1c(1), Ps1d, Ps(1-2)d, and Ps(1-2)d(1) specific to epitopes related to the lateral sugar substituents of the OPSs, were produced against P. syringae serogroup O1 strains. By using MAbs, some specific epitopes were inferred, serogroup O1 strains were serotyped in more detail, and thus, the serological classification scheme of P. syringae was improved. Screening with MAbs of about 800 strains representing all 56 known P. syringae pathovars showed that the strains classified in serogroup O1 were found among 15 pathovars and the strains with the linear OPSs of chemotype 1A were found among 9 of the 15 pathovars. A possible role for the LPS of P. syringae and related pseudomonads as a phylogenetic marker is discussed.
Lipopolysaccharide, lipopolysaccharides, LPS, strain, structural, characterization, polysaccharide, polysaccharides, Pseudomonas, antibody, epitope, monoclonal, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, serogroup, evaluation, backbone, immunochemical, Pseudomonas syringae, classification, linear, taxonomic, D-rhamnose
NCBI PubMed ID: 10559159Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Ltvlov@uta.fi
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Tampere, Finland, Pathologie Vegetale, Institut National de la Recherche Agronomique, Beaucouze Cedex, France
Methods: NMR
- Article ID: 1198
Senchenkova SN, Huang X, Laux P, Knirel YA, Shashkov AS, Rudolph K "Structures of the O-polysaccharide chains of the lipopolysaccharides of Xanthomonas campestris pv. phaseoli var. fuscans GSPB 271 and Xanthomonas campestris pv. malvacearum GSPB 1386 and GSPB 2388" -
Carbohydrate Research 337(19) (2002) 1723-1728
Lipopolysaccharide, lipopolysaccharides, LPS, structure, strain, structural, characterization, polysaccharide, Pseudomonas, chain, O-polysaccharide, O polysaccharide, bacteria, backbone, immunochemical, Pseudomonas syringae, Xanthomonas, Xanthomonas campestris, D-rhamnose
Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Moscow,Russia
Methods: NMR
- Article ID: 1246
Spitali M, Patel M, Smith ARW "Structures of lipopolysaccharide side-chains of NCPPB 2995, the neopathotype strain of Pseudomonas syringae pv morsprunorum and three other strains, in relation to O-serogroup" -
Phytopathologische Zeitschrift = Journal of Phytopathology 143(11-12) (1995) 671-677
Side-chains from the lipopolysaccharides (LPSs) of three virulent isolates of Pseudomonas syringae pv. mors-prunorum all contained D-rhamnose. Using Smith degradation, 'H- and 13C-nuclear magnetic resonance spectroscopy, methylation analysis, and GC-MS, the side-chain of strain CFBP 2115 was shown to consist of the repeat sequence: [formula: see text]. NCPPB 2995, the neopathotype strain of P. syringae pv. mors-prunorum, contained an identical side-chain, which co-purified with a gly-cogen-like polymer composed of terminal, 1,4,6- and 1,4-linked D-glucose residues in the ratio 1:1: 2.25. The side-chain of P. syringae pv. mors-prunorum strain NCPPB 2422 bore the same backbone structure as CFBP 2115, but was substituted by up to 80+ACU- with branch D-fucofuranose residues: [formula: see text]. From the pattern of hydrolysis by phage A7 rhamnanase, the tetra-and trisaccharide repeat sequences appeared to be irregularly interspersed. The side-chain from LPS of P. syringae pv. syringae strain C414 was of similar structure, but was only 35+ACU- fucosylated. Side-chain structures are correlated with a previously proposed serogrouping system.
Lipopolysaccharide, structure, strain, Pseudomonas, side chain, Pseudomonas syringae, O-serotype
Journal NLM ID: 9875585Publisher: Berlin: Parey
Institutions: School of Biological and Chemical Sciences, University of Greenwich, London SE18 6PF, UK
Methods: 13C NMR, 1H NMR, methylation, Smith degradation, serological methods
- Article ID: 1452
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 1464
Knirel YA, Kocharova NA "Structure and properties of the common polysaccharide antigen of Pseudomonas aeruginosa" -
Biochemistry (Moscow) 60(12) (1995) 1499-1507
The review is devoted to a surface carbohydrate antigen of the bacterium Pseudomonas aeruginosa which is common for the majority of the species and has a lipopolysaccharide nature. The occurrence, detection, isolation, structure, expression on the cell surface, interaction with antibodies, an antibiotic and a bacteriophage as well as the immunotherapeutic potential of the common polysaccharide antigen are discussed.
Lipopolysaccharide, structure, polysaccharide, Pseudomonas aeruginosa, monoclonal antibody, outer membrane, surface antigen, common polysaccharide antigen
NCBI PubMed ID: 8600991Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1465
Knirel YA, Zdorovenko GM "Structures of O-polysaccharide chains of lipopolysaccharides as the basis for classification of Pseudomonas syringae and related strains" -
Book: Pseudomonas Syringae Pathovars and Related Pathogens (series: Developments in Plant Pathology) (1997) 475-480
The O-polysaccharides of various serogroups of P. syringae were found to have similar structures with the main chain of a rhamnan which may carry a monosaccharide side chain of D-rhamnose, D-fucose, 2-acetamido-2-deoxy-D-glucose or 3-acetamido-3,6-dideoxy-D-galactose. The relationship between the serological specificity and the host-plant specificity of P. syringae and the structures of the O-polysaccharides is discussed.
Lipopolysaccharide, structure, O-antigen, O-polysaccharide, serological specificity, Pseudomonas syringae, Serogrouping, Host-plant specificity
Publication DOI: 10.1007/978-94-011-5472-7_85Publisher: Springer Netherlands
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead D, Vivian A, von Kietzell J
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Leninsky Pr. 47, Moscow B-334, Russia, D.K. Zabolotny Institute of Microbiology and Virology, Zabolotnogo 154, Kiev-143, Ukraine
- Article ID: 1777
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1852
Knirel YA, Zdorovenko GM, Shashkov AS, Mamyan SS, Yakovleva LM, Solyanik LP, Zakharova IY "Antigenic polysaccharides of bacteria. 26. Structure of O-specific polysaccharide chains of lipopolysaccharides from Pseudomonas cerasi 467 and Pseudomonas syringae pv. syringae strains 218 and P-55, belonging to serogroups II and III" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14 (1988) 82-91
Serologically active O-specific polysaccharides were obtained on mild acid hydrolysis of lipopolysaccharides from Pseudomonas cerasi 467 and Pseudomonas syringae pv. syringae strains 218 and P-55. On the basis of 1H- and 13C-NMR analysis, it was concluded that the P. cerasi polysaccharide has the following structure: →3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→ which is identical to that of O-specific polysaccharide from P. syringae pv. morsprunorum C28 (Smith A. R. W. et al. Eur. J. Biochem., 1985, V. 149, No 1, p. 73-78). The polysaccharides from P. syringae pv. syringae strains possess the same backbone but differ by the presence of D-fucose as monosaccharide branches. Methylation and 1H- and 13C-NMR analysis revealed the following structure of these polysaccharides: (Formula: see text). The degree of substitution of the backbone trisaccharide units by the fucofuranose residues is about 35% for the strain 218 and about 85% for the strain P-55.
NCBI PubMed ID: 2454625Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR
- Article ID: 1860
Kocharova NA, Knirel YA, Kochetkov NK, Stanislavsky ES "Characterization of a rhamnan derived from preparations of Pseudomonas aeruginosa lipopolysaccharides" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14(6) (1988) 701-703
A polysaccharide isolated from the degraded lipopolysaccharides of P. aeruginosa serogroup O7 (Lányi--Bergan classification) was characterized by liquid chromatography, acid hydrolysis, and 1H and 13C NMR spectroscopy. It has molecular mass 15,000 and represents mainly a rhamnan of the structure →2)-α-D-Rha-(1→3)-α-D-Rha-(1→3)-α-D-Rha-(1→, identical to the structure of O-specific polysaccharides of Pseudomonas aeruginosa pvs morsprunorum and cerasi. Some minor constituents, such as glucose, mannose, an unknown sugar, and phosphate, are found in the polysaccharide preparation as well. Distribution of the rhamnan in some other P. aeruginosa serogroups is discussed and its identity to the common polysaccharide antigen of P. aeruginosa is suggested.
NCBI PubMed ID: 2458737Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR
- Article ID: 1931
Arsenault TL, Hughes DW, MacLean DB, Szarek WA, Kropinski AM, Lam JS "Structural studies on the polysaccharide portion of "A-band" lipopolysaccharide from a mutant (AK1401) of Pseudomonas aeruginosa strain PAO1" -
Canadian Journal of Chemistry 69(8) (1991) 1273-1280
AK1401 is a mutant of Pseudomonas aeruginosa strain PAO1 (serotype 05) that does not express O-antigen, but does express "A-band" lipopolysaccharide (LPS). The polysaccharide portion of the A-band LPS (A-PS) from AK1401 was found to consist mainly of D-rhamnose, with smaller amounts of 3-O-methylrhamnose, ribose, mannose, glucose, and a 3-O-methylhexose. 1H nuclear magnetic resonance spectra of the intact A-PS indicated that the main structural feature was a repeating trisaccharide of α-D-rhamnose having the following structure: [formula: see text]. The 1H NMR spectrum of the repeating unit was completely assigned through the use of 2D shift-correlated and relayed coherence transfer NMR spectroscopy. The linkage positions and sequence of residues were found by nuclear Overhauser enhancement difference spectroscopy.
Lipopolysaccharide, Pseudomonas aeruginosa, 1H NMR
Publication DOI: 10.1139/v91-190Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Department of Chemistry, McMaster University, Hamilton, Ont., Canada, Department of Chemistry, Queen's University, Kingston, Ont., Canada, Department of Microbiology, University of Guelph, Guelph, Ont., Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, nOe
- Article ID: 1932
Arsenault TL, MacLean DB, Zou W, Szarek WA "Smith-degradative studies on the polysaccharide portion of A-band lipopolysaccharide from a mutant (AK1401) of Pseudomonas aeruginosa strain PAO1" -
Canadian Journal of Chemistry 72(5) (1994) 1376-1382
Hepta-O-acetyl-O-α-D-Rhap-(1 → 3)-O-α-D-Rhap-(1 → 2)-glycerol (5) was the major component derived by way of Smith degradation of A-band polysaccharide (a D-rhamnan isolated from a mutant, AK1401, of Pseudomonas aeruginosa strain PAO1). The structure has been verified by an unambiguous synthesis of 5. Based on mass spectrometric evidence, hepta-O-acetyl-O-Ribp-(1 → 3)-O-α-D-Rhap-(1 → 2)-glycerol is considered to be one of the minor components. The Smith degradation of A-band polysaccharide and the synthesis of 5 are reported.
Publication DOI: 10.1139/v94-172Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Department of Clzevzistty, McMaster University, Hamilton, ON L8S 4M1, Canada, Department of Ctzernistry, Queen's University, Kingston, ON K7L 3N6, Canada
Methods: GC-MS, NMR, TLC, Smith degradation, chemical synthesis, HPLC, optical rotation measurement
- Article ID: 2188
Vinogradov EV, Shashkov AS, Knirel YA, Zdorovenko GM, Solyanik LP, Gvozdyak RI "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide chain of Pseudomonas syringae pv. syringae (cerasi) 435 lipopolysaccharide" -
Carbohydrate Research 212 (1991) 295-299
No abstract available
NCBI PubMed ID: 1720346Publication DOI: 10.1016/0008-6215(91)84069-qJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow
Methods: 13C NMR, methylation, GLC-MS, sugar analysis, GLC, Smith degradation, GPC
- Article ID: 2407
Yokota SI, Kaya S, Sawada S, Kawamura T, Araki Y, Ito E "Characterization of a polysaccharide component of lipopolysaccharide from Pseudomonas aeruginosa IID 1008 (ATCC 27584) as D-rhamnan" -
European Journal of Biochemistry 167 (1987) 203-209
Structural studies were carried out on a rhamnose-rich polysaccharide isolated from the O-polysaccharide fraction of lipopolysaccharide in Pseudomonas aeruginosa IID 1008 (ATCC 27584) after destruction of the major O-specific chain by alkaline treatment. The isolated polysaccharide contained rhamnose, 3-O-methyl-6-deoxyhexose, glucose, xylose, alanine, galactosamine and phosphorus in a molar ratio of 67:6.9:4.3:2.1:1.1:1.0:4.1. Data from analysis involving Smith degradation, methylation, 1H-NMR spectroscopy and optical rotation measurement showed that the polysaccharide was built up of three moieties, a rhamnan chain composed of about 70 D-rhamnose residues, the core chain and an oligosaccharide chain comprising 3-O-methyl-6-deoxyhexose, xylose, rhamnose and probably glucose. The repeating unit of the rhamnan chain was indicated to have the following structure: →3)D-Rha(α1→3)D-Rha(α1→2)D-Rha(α1→. This structure is identical with that proposed previously for the repeating unit of the side chain of lipopolysaccharide from plant pathogenic bacteria Pseudomonas syringae pv. morsprunorum C28 [Smith, A.R.W., Zamze, S.E., Munro, S.M., Carter, K. J. and Hignett, R.C. (1985) Eur. J. Biochem. 149, 73-78].
NCBI PubMed ID: 3113949Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: 1H NMR, GC-MS
- Article ID: 2789
Ovod V, Ashorn P, Yakovleva L, Krohn K "Classification of Pseudomonas syringae with monoclonal antibodies against the core and O-side chains of the lipopolysaccharide" -
Phytopathology 85 (1995) 226-232
Journal NLM ID: 9427222Publisher: American Phytopathological Society
- Article ID: 3411
Faure R, Shiao TC, Lagnoux D, Giguere D, Roy R "En route to a carbohydrate-based vaccine against Burkholderia cepacia" -
Organic and Biomolecular Chemistry 5(16) (2007) 2704-2708
We report a very high yielding first total synthesis of trisaccharide 5, α-D-Rhap-(1→3)-α-D-Rhap-(1→4)-α-D-Galp, corresponding to the repeating unit 1 of an O-polysaccharide present in the lipopolysaccharide of clinical isolate of Burkholderia cepacia. The approach included two successive glycosylations, based on D-rhamnosyl trichloroacetimidate donors 12 and 14. The oligosaccharide 5 has been further functionalized by photochemical coupling or cross-metathesis with non-natural amino acid derivatives. Trisaccharidylamino acids 16 and 17 are now available, with the aim of preparing a novel synthetic carbohydrate-based vaccine
synthesis, Burkholderia cepacia, repeating unit, trisaccharide, O-polysaccharide, glycosylation, vaccine, Synthetic
NCBI PubMed ID: 18019546Publication DOI: 10.1039/b708365cJournal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Institutions: Equipe PharmaQAM, Departement de Chimie, Universite du Quebec a Montreal, P.O. Box 8888, Succ. Centre-Ville, H3C 3P8 Montreal, Quebec, Canada
Methods: 13C NMR, 1H NMR, ESI-MS, chemical methods, NMR-1D
- Article ID: 3546
Smith ARW "Structure of the lipopolysaccharide side-chain of Pseudomonas syringae pv. syringae strain S29" -
Phytopathologische Zeitschrift = Journal of Phytopathology 156(6) (2008) 362-364
Using 1H- and 13C-nuclear magnetic resonance spectroscopy, the repeat unit of the lipopolysaccharide side-chain from Pseudomonas syringae pv. syringae strain S29 was shown to have the following structure: 2)-b-L-Rhap(1-. This structure is identical with that of the side-chain of Pseudomonas syringae pv. mori CFPB 1656.
Pseudomonas syringae, Serogrouping, lipopolysaccharide side-chain structure
Publication DOI: 10.1111/j.1439-0434.2007.01363.xJournal NLM ID: 9875585Publisher: Berlin: Parey
Correspondence: SmiA672@aol.com
Institutions: Department of Life Science, School of Science, University of Greenwich, Medway Campus, Pembroke,Central Avenue, Chatham Maritime, Kent ME4 4TB, UK
Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, GC, composition analysis, colorimetry
- Article ID: 3582
Veremeichenko SN, Zdorovenko GM "Specific structural features and immunomodulatory properties of the lipopolysaccharides of Pseudomonas bacteria" -
Applied Biochemistry and Microbiology 44(6) (2008) 571-579
The results of in vitro studies of the immunomodulatory action of the lipopolysaccharides (LPS) of the Pseudomonas bacteria— P. fluorescens biovar I strains IMV 4125 = ATCC 13525, IMV 7769, and IMV 1152; P. fluorescens biovar IV strain IMV 2111; P. syringae pv. syringae IMV 281 = CPPB 281 = ATCC 19310 and IMV 467; and P. wieringae IMV 7923—on the mouse spleenocytes and human peripheral blood mononuclear cells (PBMC), B lymphocytes, and T lymphocytes are described. The proliferative activity of mouse spleenocytes correlated with the degree of LPS toxicity. The PBMC mitogenic activity induced by the P. fluorescens IMV 7769 LPS preparation exceeded the activity of E. coli 026: B6 LPS. The immunomodulatory effect of LPS on T cells was strain and dose dependent. The LPS of P. syringae pv. syringae INV 467 displayed a comparatively pronounced immunomodulatory effect on human blood B lymphocytes.
lipopolysaccharides, structural, Pseudomonas, specific, immunomodulatory
NCBI PubMed ID: 19145969Journal NLM ID: 0042510Publisher: Kluwer Academic/Plenum Publishers
Correspondence: stas@diapr.kiev.ua
Institutions: Research and Production Company Diaprof-Med, Kiev, 04123 Ukraine, Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, 02143 Ukraine
Methods: serological methods
- Article ID: 3743
Molinaro A, Newman M, Lanzetta R, Parrilli M "The structures of lipopolysaccharides from plant-associated Gram-negative bacteria" -
European Journal of Organic Chemistry 2009(34) (2009) 5887-5896
Gram-negative bacterial lipopolysaccharides (LPSs) have multiple roles in plant-microbe interactions. LPSs contribute to the low permeabilities of bacterial outer membranes, which act as barriers to protect bacteria from plant-derived antimicrobial substances. Conversely, perception of LPSs by plant cells can lead to the triggering of defence responses or to the priming of the plant to respond more rapidly and/or to a greater degree to subsequent pathogen challenge. LPSs are thus key molecules in the interactions between bacteria and plants, either in symbiosis or pathogenesis. Since LPSs are glycoconjugates genetically and chemically consisting of three different molecular regions, their detailed structure elucidation is a very topical and major scientific task for chemists, and is achieved by a combination of state-of-art chemical and spectroscopic techniques. Knowledge of LPSs' chemical structures is an important prerequisite for any further understanding of the biological processes in plant-microbe interactions. Moreover, the LPSs from Gram-negative bacteria - especially those originating from plant-associated bacteria - are a great source of novel monosaccharides with unusual and occasionally astounding chemical structures, never found in the eukaryotic world. This review presents the structures of LPSs from plant-associated bacteria isolated and identified from 2001 onwards.
lipopolysaccharides, structure elucidation, glycolipids, innate immunity, immunochemistry, plant-associated bacteria
Publication DOI: 10.1002/ejoc.200900682Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: molinaro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli “Federico II”, via Cinthia 4, 80126 Napoli, Italy, Fax: +39-081-674393, Faculty of Life Sciences, Department of Plant Biology & Biotechnology, University of Copenhagen, 1871 Frederiksberg, Denmark
- Article ID: 3968
Zdorovenko GM, Zdorovenko EL "Pseudomonas syringae lipopolysaccharides: Immunochemical characteristics and structure as a basis for strain classification" -
Mikrobiologiia = Microbiology [Russian] 79(1) (2010) 47-57
Lipopolysaccharide (LPS) preparations of 34 Pseudomonas syringae strains of 19 pathovars were prepared by saline extraction from wet cells and purified by repeated ultracentrifugation. The preparations reacted with homologous O-antisera, obtained by rabbit immunization with heat-killed bacterial cells. Through inhibition of homologous reactions between LPS preparations of heterologous strains (enzyme immunoassay, EIA), it was established for the first time that high serological affinity between strains is observed only if their LPS contains O-specific polysaccharide chains (OPS) comprised of completely identical rather than partially similar units. The central linear part of the OPS was found to be serologically inert when shielded with side groups. Data on immunochemical characteristics of the LPS and OPS structure are analyzed in relation to the design of P. syringae classification scheme.
Lipopolysaccharide, structure, O-specific polysaccharide, Pseudomonas syringae, classification, immunochemistry
NCBI PubMed ID: 20411661Publication DOI: 10.1134/S0026261710010078Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: evelina@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kyiv, 03143 Ukraine
Methods: partial acid hydrolysis, EIA, serological methods, de-N-acetylation/deamination
- Article ID: 4306
Greenfield LK, Whitfield C "Synthesis of lipopolysaccharide O-antigens by ABC transporter-dependent pathways" -
Carbohydrate Research 356 (2012) 12-24
The O-polysaccharide (O-PS; O-antigen) of bacterial lipopolysaccharides is made up of repeating units of one or more sugar residues and displays remarkable structural diversity. Despite the structural variations, there are only three strategies for O-PS assembly. The ATP-binding cassette (ABC)-transporter-dependent mechanism of O-PS biosynthesis is widespread. The Escherichia coli O9a and Klebsiella pneumoniae O2a antigens provide prototypes, which are distinguished by the fine details that link glycan polymerization and chain termination at the cytoplasmic face of the inner membrane to its export via the ABC transporter. Here, we describe the current understanding of these processes. Since glycoconjugate assembly complexes that utilize an ABC transporter-dependent pathway are widespread among the bacterial kingdom, the models described here are expected to extend beyond O-PS biosynthesis systems
Lipopolysaccharide, O-polysaccharide, ATP-binding cassette transporter, Escherichia coli O9a, Klebsiella pneumoniae O2a
NCBI PubMed ID: 22475157Publication DOI: 10.1016/j.carres.2012.02.027Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: C. Whitfield
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada N1G 2W1
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4527
Hao Y, King JD, Huszczynski S, Kocincova D, Lam JS "Five New Genes Are Important for Common Polysaccharide Antigen Biosynthesis in Pseudomonas aeruginosa" -
mBio 4(1) (2013) e00631-12
ABSTRACT. Common polysaccharide antigen (CPA) is a conserved cell surface polysaccharide produced by Pseudomonas aeruginosa. It contains a rhamnan homopolymer and is one of the two forms of O polysaccharide attached to P. aeruginosa lipopolysaccharide (LPS). Our laboratory has previously characterized an eight-gene cluster (pa5447-pa5454 in P. aeruginosa PAO1) required for biosynthesis of CPA. Here we demonstrate that an adjacent five-gene cluster pa5455-pa5459 is also involved. Using reverse transcriptase PCR (RT-PCR), we showed that the original eight-gene cluster and the new five-gene cluster are both organized as operons. We have analyzed the LPS phenotypes of in-frame deletion mutants made in each of the five genes, and the results verified that these five genes are indeed required for CPA biosynthesis, extending the CPA biosynthesis locus to contain 13 contiguous genes. By performing overexpression experiments of different sets of these biosynthesis genes, we were able to obtain information about their possible functions in CPA biosynthesis. IMPORTANCE. Lipopolysaccharide (LPS) is an important cell surface structure of Gram-negative bacteria. The human opportunistic pathogen Pseudomonas aeruginosa simultaneously produces an O-antigen-specific (OSA) form and a common polysaccharide antigen (CPA) form of LPS. CPA, the focus of this study, is composed of α-1-2, α-1-3-linked d-rhamnose sugars and has been shown to be important for attachment of the bacteria to human airway epithelial cells. Genome sequencing of this species revealed a new five-gene cluster that we predicted to be involved in CPA biosynthesis and modification. In this study, we have generated chromosomal knockouts by performing in-frame deletions and allelic replacements. Characterizing the function of each of the five genes is important for us to better understand CPA biosynthesis and the mechanisms of chain length termination and regulation of this unique D-rhamnan polysaccharide.
biosynthesis, Pseudomonas aeruginosa, rhamnan, genome sequencing
NCBI PubMed ID: 23341552Publication DOI: 10.1128/mBio.00631-12Journal NLM ID: 101519231Publisher: Washington, DC: American Society for Microbiology
Correspondence: Joseph S. Lam
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada
Methods: PCR, genetic methods
- Article ID: 4637
Wang S, Tanaka H, Hindsgaul O, Lam JS, Brockhausen I "A convenient synthesis of GDP-d-rhamnose: The donor substrate for D-rhamnosyltransferase WbpZ from Pseudomonas aeruginosa PAO1" -
Bioorganic and Medicinal Chemistry Letters 23(12) (2013) 3491-3495
Gram negative bacteria have lipopolysaccharides (LPS) that are critical for their survival. LPS molecules are composed of antigenic exopolysaccharide chains (O antigens). We are interested in discovering the enzymes involved in the biosynthesis of O antigens in Pseudomonas aeruginosa. The common polysaccharide antigen contains α-linked d-rhamnose residues. We have now synthesized GDP-d-rhamnose by a convenient synthesis in aqueous solution, and have shown that it can be used without extensive purification as the donor substrate for d-rhamnosyltransferase (WbpZ) from the P. aeruginosa strain PAO1. The availability of this nucleotide sugar preparation allows for characterization of d-rhamnosyltransferases.
Pseudomonas aeruginosa, O-antigens, D-Rha-transferase, WbpZ, GDP-D-Rha
NCBI PubMed ID: 23664878Publication DOI: 10.1016/j.bmcl.2013.04.051Journal NLM ID: 9107377Publisher: Elsevier
Correspondence: I. Brockhausen
Institutions: Department of Medicine, Queen's University, Kingston, Ontario, Canada K7L 3N6, Department of Biomedical and Molecular Sciences, Queen's University, Kingston, Ontario, Canada K7L 3N6, Carlsberg Laboratory, Copenhagen-V DK-1799, Denmark
Methods: 1H NMR, glycosyltransferase assays, ESI-MS, MALDI-MS, Western blotting, chemical synthesis, biochemical methods
- Article ID: 4808
Wang S, Hao Y, Lam JS, Vlahakis JZ, Szarek WA, Vinnikova A, Veselovsky VV, Brockhausen I "Biosynthesis of the Common Polysaccharide Antigen of Pseudomonas aeruginosa PAO1: Characterization and role of GDP-D-rhamnose: GlcNAc/GalNAc-diphosphate-lipid a1,3-D-rhamnosyltransferase WbpZ" -
Journal of Bacteriology 197(12) (2015) 2012-2019
The opportunistic pathogen Pseudomonas aeruginosa produces two major cell surface lipopolysaccharides, characterized by distinct O antigens, called Common Polysaccharide Antigen (CPA) and O-specific antigen (OSA). CPA contains a polymer of D-rhamnose (D-Rha) in α-2 and α-3-linkages. Three putative glycosyltransferase genes, wbpX, wbpY, and wbpZ, are part of the CPA biosynthesis cluster. To characterize the enzymatic function of the wbpZ gene product, we chemically synthesized the donor substrate GDP-D-Rha and enzymatically synthesized GDP-D-[3H]Rha. Using NMR spectroscopy, we showed that WbpZ transferred one D-Rha residue from GDP-D-Rha in α1-3 linkage to both, GlcNAc- and GalNAc-diphosphate-lipid acceptor substrates. WbpZ is also capable of transferring D-mannose (D-Man) to these acceptors. Therefore, WbpZ has a relaxed specificity with respect to both, acceptor and donor substrates. The diphosphate group of the acceptor, however, is required for activity. WbpZ does not require divalent metal ion for activity and exhibits an unusually high pH optimum of 9. WbpZ from PAO1 is therefore a GDP-D-Rha: GlcNAc/GalNAc-diphosphate-lipid α1,3-D-rhamnosyltransferase that has significant activity of GDP-D-Man: GlcNAc/GalNAc-diphosphate-lipid α1,3-D-mannosyltransferase. We used site-directed mutagenesis to replace the Asp residues of the two DXD motifs with Ala. Neither of the mutant constructs of wbpZ (D172A or D254A) could be used to rescue CPA biosynthesis in the ∆wbpZ knockout mutant in a complementation assay. This suggested that D172 and D254 are essential for WbpZ function. This work is the first detailed characterization study of a D-Rha-transferase and a critical step in the development of CPA synthesis inhibitors. IMPORTANCE: This is the first characterization of a D-rhamnosyltransferase and shows that it is essential in Pseudomonas aeruginosa for the synthesis of the Common Polysaccharide Antigen.
O-antigen, Pseudomonas aeruginosa, glycosyltransferase, common polysaccharide antigen, D-Rha-transferase, WbpZ
NCBI PubMed ID: 25845842Publication DOI: 10.1128/JB.02590-14Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: brockhau@queensu.ca (Inka Brockhausen)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Molecular and Cellular Biology, University of Guelph, Guelph, ON, Canada N1G 2W1, Department of Medicine, Department of Biomedical and Molecular Sciences, Queens University, Kingston, Ontario, Canada K7L 3N6, Department of Chemistry, Queens University, Kingston, Ontario, Canada K7L 3N6
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, SDS-PAGE, DNA techniques, glycosyltransferase assays, kinetics assays, ESI-MS, Western blotting, NMR-1D, genetic methods, biochemical methods, radioactivity measurement, HPLC, mutation analysis, RP-HPLC, enzymatic synthesis
- Article ID: 5143
Cloutier M, Muru K, Ravicoularamin G, Gauthier C "Polysaccharides from Burkholderia species as targets for vaccine development, immunomodulation and chemical synthesis" -
Natural Product Reports 35(12) (2018) 1251-1293
Burkholderia species are a vast group of human pathogenic, phytopathogenic, and plant- or environment-associated bacteria. B. pseudomallei, B. mallei, and B. cepacia complex are the causative agents of melioidosis, glanders, and cystic fibrosis-related infections, respectively, which are fatal diseases in humans and animals. Due to their high resistance to antibiotics, high mortality rates, and increased infectivity via the respiratory tract, B. pseudomallei and B. mallei have been listed as potential bioterrorism agents by the Centers for Disease Control and Prevention. Burkholderia species are able to produce a large network of surface-exposed polysaccharides, i.e., lipopolysaccharides, capsular polysaccharides, and exopolysaccharides, which are virulence factors, immunomodulators, major biofilm components, and protective antigens, and have crucial implications in the pathogenicity of Burkholderia-associated diseases. This review provides a comprehensive and up-to-date account regarding the structural elucidation and biological activities of surface polysaccharides produced by Burkholderia species. The chemical synthesis of oligosaccharides mimicking Burkholderia polysaccharides is described in detail. Emphasis is placed on the recent research efforts toward the development of glycoconjugate vaccines against melioidosis and glanders based on synthetic or native Burkholderia oligo/polysaccharides.
lipopolysaccharides, Burkholderia, capsular polysaccharides, Oligosaccharides, glycoconjugate vaccines, antigens, exopolysaccharides, surface polysaccharide, virulence factor, Biofilm, chemical synthesis, bioterrorism
Publication DOI: 10.1039/C8NP00046HJournal NLM ID: 8502408Publisher: London: Royal Society of Chemistry
Correspondence: charles.gauthier@iaf.inrs.ca
Institutions: INRS-Institut Armand-Frappier, Universite du Quebec, 531, boul. des Prairies, Laval, Canada
- Article ID: 6206
Cairns C, St Michael F, Jamshidi MP, van Faassen H, Yang Q, Henry KA, Hussack G, Sauvageau J, Vinogradov EV, Cox AD "Structural Characterization and Evaluation of an Epitope at the Tip of the A-Band Rhamnan Polysaccharide of Pseudomonas aeruginosa" -
ACS Infectious Diseases 8(7) (2022) 1336-1346
Pseudomonas aeruginosa produces a variety of cell surface glycans. Previous studies identified a common polysaccharide (PS) antigen often termed A-band PS that was composed of a neutral d-rhamnan trisaccharide repeating unit as a relatively conserved cell surface carbohydrate. However, nuclear magnetic resonance (NMR) spectra and chemical analysis of A-PS preparations showed the presence of several additional components. Here, we report the characterization of the carbohydrate component responsible for these signals. The carbohydrate antigen consists of an immunogenic methylated rhamnan oligosaccharide at the nonreducing end of the A-band PS. Initial studies performed with the isolated antigen permitted the production of conjugates that were used to immunize mice and rabbits and generate monoclonal and polyclonal antibodies. The polyclonal antibodies were able to recognize the majority of P. aeruginosa strains in our collection, and three monoclonal antibodies were generated, one of which was able to recognize and facilitate opsonophagocytic killing of a majority of P. aeruginosa strains. This monoclonal antibody was able to recognize all P. aeruginosa strains in our collection that includes clinical and serotype strains. Synthetic oligosaccharides (mono- to pentasaccharides) representing the terminal 3-O-methyl d-rhamnan were prepared, and the trisaccharide was identified as the antigenic determinant required to effectively mimic the natural antigen recognized by the broadly cross-reactive monoclonal antibody. These data suggest that there is considerable promise in this antigen as a vaccine or therapeutic target.
Lipopolysaccharide, Pseudomonas aeruginosa, monoclonal antibody, glycoconjugate vaccine, common polysaccharide antigen, methylrhamnan
NCBI PubMed ID: 35653593Publication DOI: 10.1021/acsinfecdis.2c00183Journal NLM ID: 101654580Publisher: Washington, DC: American Chemical Society
Correspondence: A.D. Cox
Institutions: Vaccine and Emerging Infections Research, Human Health Therapeutics Research Centre, National Research Council, Ottawa, Ontario K1A 0R6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, ELISA, ESI-MS, anion-exchange chromatography, MALDI-MS, chemical synthesis, HPLC, serum bactericidal assays, periodate oxidation, gel chromatography, SEC, SPR, immunization, conjugation, alkaline treatment, opsonophagocytic assay, isolation, mAb epitope mapping
- Article ID: 6211
Del Bino L, Osterlid KE, Wu DY, Nonne F, Romano MR, Codée J, Adamo R "Synthetic Glycans to Improve Current Glycoconjugate Vaccines and Fight Antimicrobial Resistance" -
Chemical Reviews 122(20) (2022) 15672-15716
Antimicrobial resistance (AMR) is emerging as the next potential pandemic. Different microorganisms, including the bacteria Acinetobacter baumannii, Clostridioides difficile, Escherichia coli, Enterococcus faecium, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, non-typhoidal Salmonella, and Staphylococcus aureus, and the fungus Candida auris, have been identified by the WHO and CDC as urgent or serious AMR threats. Others, such as group A and B Streptococci, are classified as concerning threats. Glycoconjugate vaccines have been demonstrated to be an efficacious and cost-effective measure to combat infections against Haemophilus influenzae, Neisseria meningitis, Streptococcus pneumoniae, and, more recently, Salmonella typhi. Recent times have seen enormous progress in methodologies for the assembly of complex glycans and glycoconjugates, with developments in synthetic, chemoenzymatic, and glycoengineering methodologies. This review analyzes the advancement of glycoconjugate vaccines based on synthetic carbohydrates to improve existing vaccines and identify novel candidates to combat AMR. Through this literature survey we built an overview of structure-immunogenicity relationships from available data and identify gaps and areas for further research to better exploit the peculiar role of carbohydrates as vaccine targets and create the next generation of synthetic carbohydrate-based vaccines.
carbohydrates, glycan, glycoconjugate vaccine
NCBI PubMed ID: 35608633Publication DOI: 10.1021/acs.chemrev.2c00021Journal NLM ID: 2985134RPublisher: Chem Rev
Correspondence: J. Codée
; R. Adamo
Institutions: GSK, R&D, 53100 Siena, Italy, Leiden Institute of Chemistry, Leiden University, 2300 RA Leiden, The Netherlands
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4. Compound ID: 1206
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_1394181,IEDB_145005,IEDB_145006,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 380
Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" -
APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.
Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics
NCBI PubMed ID: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
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5. Compound ID: 1466
|
a-D-Fucp3NAc-(1-2)-+
|
a-D-Fucp3NAc-(1-2)-+ |
| |
Me-3)-{{{-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1-3)-}}}/n=16/-{{{-a-D-Rhap-(1-3)-}}}/n=1-3/-b-D-GalpNAc-(1--/Thr67 of S-layer protein/ |
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Structure type: oligomer
Aglycon: Thr67 of S-layer protein
Compound class: S-layer glycoprotein
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1394181,IEDB_144827,IEDB_145005,IEDB_145006,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 467
Schäffer C, Messner P "Surface-layer glycoproteins: an example for the diversity of bacterial glycosylation with promising impacts on nanobiotechnology" -
Glycobiology 14(8) (2004) 31R-42R
Bacterial cell surface layers, referred to simply as S-layers, have been described for all major phylogenetic groups of bacteria, which may indicate their pivotal role for a bacterium in its natural habitat. They have the unique ability to assemble into two-dimensional crystalline arrays that completely cover the bacterial cells. Glycosylation represents the most frequent modification of S-layer proteins. S-layer glycoproteins constitute a class of glycoconjugates first isolated in the mid-1970s, but S-layer glycoprotein research is still being regarded as an 'exotic field of glycobiology,' possibly because of its 'noneukaryotic' character. Extensive work over the past 30 years provided evidence of an enormous diversity of S-layer glycoproteins that have been created in nature over 3 billion years of prokaryotic evolution. These glycoconjugates are substantially different from eukaryotic glycoproteins, with regard to both composition and structure; nevertheless, some general structural concepts may be deduced. The awareness of the high application potential of S-layer glycoproteins, especially in combination with their intrinsic cell surface display feature, in the field of modern nanobiotechnology as a base for glycoengineering has recently led to the investigation of the S-layer protein glycosylation process at the molecular level, which has lagged behind the structural studies due to the lack of suitable molecular tools. From that work an even more interesting picture of this class of glycoconjugates is emerging. The availability of purified enzymes from S-layer glycan biosynthesis pathways exhibiting increased stabilities and/or rare sugar specificities in conjunction with preliminary genomic data on S-layer glycan biosynthesis clusters will pave the way for the rational design of S-layer neoglycoproteins.
LPS, bacterial glycosylation, genomic glycosylation loci, glycan diversity, glycoengineering, S-layer nanoglycobiology
NCBI PubMed ID: 15044388Publication DOI: 10.1093/glycob/cwh064Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: paul.messner@boka.ac.at
Institutions: Center for NanoBiotechnology, University of Applied Life Sciences and Natural Resources, Gregor-Mendel-Strasse 33, A-1180 Wien, Austria
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6. Compound ID: 1480
|
a-Yerp-(1-2)-+
|
-2)-a-D-Rhap-(1-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-
Yer = 3,6-dideoxy-4-C-[(S)-1-hydroxyethyl]-D-xylo-hexose (yersiniose A) |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_1394181,IEDB_144831,IEDB_145005,IEDB_145006,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 468
Mattos KA, Todeschini AR, Heise N, Jones C, Previato JO, Mendonça-Previato L "Nitrogen-fixing bacterium Burkholderia brasiliensis produces a novel yersiniose A-containing O-polysaccharide" -
Glycobiology 15(3) (2005) 313-321
Burkholderia brasiliensis, a Gram-negative diazotrophic endophytic bacterium, was first isolated from roots, stems and leaves of rice plant in Brazil. The polysaccharide moiety was released by ammonolysis from the B. brasiliensis lipopolysaccharide (LPS), allowing the unambiguous characterization of a 3,6-dideoxy-4-C-(1-hydroxyethyl)-D-xylo-hexose (Yersiniose A), an uncommon feature for Burkholderia LPS. The complete structure of the yersiniose A-containing O-antigen was identified by sugar and methylation analyses and nuclear magnetic resonance spectroscopy. Our results show that the repeating oligosaccharide motif of LPS O-chain consists of a branched tetrasaccharide with the following structure: →2-α-D-Rhap-(1→3)-[α-YerAp-(1→2)]-α-D-Rhap-(1→3)-α-D-Rhap-(1→
Lipopolysaccharide, LPS, oligosaccharide, structure, branched, tetrasaccharide, characterization, polysaccharide, Burkholderia, O-antigen, O antigen, O-polysaccharide, O polysaccharide, bacteria, sugar, motif, methylation, Magnetic Resonance Spectroscopy, nuclear, nuclear magnetic resonance, nuclear magnetic resonance spectroscopy, resonance, spectroscopy, Gram-negative, O-chain, plant, leaf, nitrogen fixing, root, yersiniose
NCBI PubMed ID: 15509723Publication DOI: 10.1093/glycob/cwi009Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: luciamp@biof.ufrj.br
Institutions: Instituto de Biofisica Carlos Chagas Filho, Centro de Ciencias da Saude, Bloco G, Universidade Federal do Rio de Janeiro, 21944-970, Cidade Universitaria, Ilha do Fundao, Rio de Janeiro, RJ, Brasil
Methods: NMR-2D, methylation, NMR, sugar analysis
- Article ID: 3820
Banoub JH, El Aneed A, Cohen AM, Joly N "Structural investigation of bacterial lipopolysaccharides by mass spectrometry and tandem mass spectrometry" -
Mass Spectrometry Reviews 29(4) (2010) 606-650
Mass spectrometric studies are now playing a leading role in the elucidation of lipopolysaccharide (LPS) structures through the characterization of antigenic polysaccharides, core oligosaccharides and lipid A components including LPS genetic modifications. The conventional MS and MS/MS analyses together with CID fragmentation provide additional structural information complementary to the previous analytical experiments, and thus contribute to an integrated strategy for the simultaneous characterization and correct sequencing of the carbohydrate moiety.
LPS, O-antigen, lipid A, core oligosaccharide, MS and MS/MS analyses
NCBI PubMed ID: 20589944Publication DOI: 10.1002/mas.20258Journal NLM ID: 8219702Publisher: Wiley
Correspondence: joe.banoub@dfo-mpo.gc.ca
Institutions: Fisheries and Oceans Canada, Science Branch, Special Projects, P.O. Box 5667, St. John's, Newfoundland, Canada A1C 5X1, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada A1B 3V6, College of Pharmacy and Nutrition, University of Saskatchewan, Thorvaldson Building, 110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9, Unité de Catalyse et de Chimie du Solide, Site de l'Artois—UMR CNRS 8181, I.U.T. de Béthune, Département Chimie, 1230 rue de l'Université, BP819, 62408 Béthune Cedex, France, Institute for Marine Biosciences Room 219A, (NRC-IMB), National Research Council of Canada, Government of Canada, 1411 Oxford Street, Halifax, NS, Canada B3H 3Z1
Methods: MS/MS, MS
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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7. Compound ID: 1482
|
a-D-Fucp3NAc-(1-2)-+
|
a-D-Fucp3NAc-(1-2)-+ |
| |
-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1- |
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Structure type: polymer chemical repeating unit
; n=15
Trivial name: S-layer glycoprotein
Contained glycoepitopes: IEDB_1394181,IEDB_144827,IEDB_145005,IEDB_145006,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 470
Novotny R, Pfoestl A, Messner P, Schäffer C "Genetic organization of chromosomal S-layer glycan biosynthesis loci of Bacillaceae" -
Glycoconjugate Journal 20(7-8) (2004) 435-447
S-layer glycoproteins are cell surface glycoconjugates that have been identified in archaea and in bacteria. Usually, S-layer glycoproteins assemble into regular, crystalline arrays covering the entire bacterium. Our research focuses on thermophilic Bacillaceae, which are considered a suitable model system for studying bacterial glycosylation. During the past decade, investigations of S-layer glycoproteins dealt with the elucidation of the highly variable glycan structures by a combination of chemical degradation methods and nuclear magnetic resonance spectroscopy. It was only recently that the molecular characterization of the genes governing the formation of the S-layer glycoprotein glycan chains has been initiated. The S-layer glycosylation (slg) gene clusters of four of the 11 known S-layer glycan structures from members of the Bacillaceae have now been studied. The clusters are approximately 16 to approximately 25 kb in size and transcribed as polycistronic units. They include nucleotide sugar pathway genes that are arranged as operons, sugar transferase genes, glycan processing genes, and transporter genes. So far, the biochemical functions only of the genes required for nucleotide sugar biosynthesis have been demonstrated experimentally. The presence of insertion sequences and the decrease of the G + C content at the slg locus suggest that the investigated organisms have acquired their specific S-layer glycosylation potential by lateral gene transfer. In addition, S-layer protein glycosylation requires the participation of housekeeping genes that map outside the cluster. The gene encoding the respective S-layer target protein is transcribed monocistronically and independently of the slg cluster genes. Its chromosomal location is not necessarily in close vicinity to the slg gene cluster.
bacterial glycosylation, S-layer, glycosylation gene cluster, sugar nucleotides, S-layer gene, glycan biosynthesis
NCBI PubMed ID: 15316277Publication DOI: 10.1023/B:GLYC.0000038290.74944.65Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Institutions: University of Applied Life Sciences and Natural Resources, Center for NanoBiotechnology, Gregor-Mendel Strasse 33, A-1180 Wien, Austria
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8. Compound ID: 1483
|
a-D-Fucp3NAc-(1-2)-+
|
a-D-Fucp3NAc-(1-2)-+ |
| |
Me-3)-{{{-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1-3)-}}}/n=16/-{{{-a-D-Rhap-(1-3)-}}}/n=0-2/-a-D-Rhap-(1-3)-b-D-GalpNAc-(1-3)-Thr-(?--/Thr-67 in S-layer protein/ |
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Structure type: oligomer
Aglycon: Thr-67 in S-layer protein
Trivial name: S-layer glycoprotein
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1394181,IEDB_144827,IEDB_145005,IEDB_145006,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 470
Novotny R, Pfoestl A, Messner P, Schäffer C "Genetic organization of chromosomal S-layer glycan biosynthesis loci of Bacillaceae" -
Glycoconjugate Journal 20(7-8) (2004) 435-447
S-layer glycoproteins are cell surface glycoconjugates that have been identified in archaea and in bacteria. Usually, S-layer glycoproteins assemble into regular, crystalline arrays covering the entire bacterium. Our research focuses on thermophilic Bacillaceae, which are considered a suitable model system for studying bacterial glycosylation. During the past decade, investigations of S-layer glycoproteins dealt with the elucidation of the highly variable glycan structures by a combination of chemical degradation methods and nuclear magnetic resonance spectroscopy. It was only recently that the molecular characterization of the genes governing the formation of the S-layer glycoprotein glycan chains has been initiated. The S-layer glycosylation (slg) gene clusters of four of the 11 known S-layer glycan structures from members of the Bacillaceae have now been studied. The clusters are approximately 16 to approximately 25 kb in size and transcribed as polycistronic units. They include nucleotide sugar pathway genes that are arranged as operons, sugar transferase genes, glycan processing genes, and transporter genes. So far, the biochemical functions only of the genes required for nucleotide sugar biosynthesis have been demonstrated experimentally. The presence of insertion sequences and the decrease of the G + C content at the slg locus suggest that the investigated organisms have acquired their specific S-layer glycosylation potential by lateral gene transfer. In addition, S-layer protein glycosylation requires the participation of housekeeping genes that map outside the cluster. The gene encoding the respective S-layer target protein is transcribed monocistronically and independently of the slg cluster genes. Its chromosomal location is not necessarily in close vicinity to the slg gene cluster.
bacterial glycosylation, S-layer, glycosylation gene cluster, sugar nucleotides, S-layer gene, glycan biosynthesis
NCBI PubMed ID: 15316277Publication DOI: 10.1023/B:GLYC.0000038290.74944.65Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Institutions: University of Applied Life Sciences and Natural Resources, Center for NanoBiotechnology, Gregor-Mendel Strasse 33, A-1180 Wien, Austria
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9. Compound ID: 1773
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a-D-Rhap-(1-3)-+
|
-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: D-rhamnan
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_1394181,IEDB_144831,IEDB_145005,IEDB_145006,IEDB_145007,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 554
Bedini E, Carabellese A, Michela CM, De Castro C, Parrilli M "Synthesis of a D-rhamnose branched tetrasaccharide, repeating unit of the O-chain from Pseudomonas syringae pv. Syringae (cerasi) 435" -
Carbohydrate Research 339(11) (2004) 1907-1915
The first synthesis of a d-rhamnose branched tetrasaccharide, corresponding to the repeating unit of the O-chain from Pseudomonas syringae pv. cerasi 435, as methyl glycoside is reported. The approach used is based on the synthesis of an opportune building-block, that is the methyl 3-O-allyl-4-O-benzoyl-α-D-rhamnopyranoside, which was then converted into both a glycosyl acceptor and two different protected glycosyl trichloroacetimidate donors. Successive couplings of these three compounds afforded the target oligosaccharide. The reported synthesis is also useful to perform the oligomerization of the repeating unit
synthesis, repeating unit, O-chain, Pseudomonas cerasi, D-rhamnose, oligosaccharode
NCBI PubMed ID: 15261583Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: ebedini@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli 'Federico II', Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy
- Article ID: 1452
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 1465
Knirel YA, Zdorovenko GM "Structures of O-polysaccharide chains of lipopolysaccharides as the basis for classification of Pseudomonas syringae and related strains" -
Book: Pseudomonas Syringae Pathovars and Related Pathogens (series: Developments in Plant Pathology) (1997) 475-480
The O-polysaccharides of various serogroups of P. syringae were found to have similar structures with the main chain of a rhamnan which may carry a monosaccharide side chain of D-rhamnose, D-fucose, 2-acetamido-2-deoxy-D-glucose or 3-acetamido-3,6-dideoxy-D-galactose. The relationship between the serological specificity and the host-plant specificity of P. syringae and the structures of the O-polysaccharides is discussed.
Lipopolysaccharide, structure, O-antigen, O-polysaccharide, serological specificity, Pseudomonas syringae, Serogrouping, Host-plant specificity
Publication DOI: 10.1007/978-94-011-5472-7_85Publisher: Springer Netherlands
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead D, Vivian A, von Kietzell J
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Leninsky Pr. 47, Moscow B-334, Russia, D.K. Zabolotny Institute of Microbiology and Virology, Zabolotnogo 154, Kiev-143, Ukraine
- Article ID: 1777
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 2188
Vinogradov EV, Shashkov AS, Knirel YA, Zdorovenko GM, Solyanik LP, Gvozdyak RI "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide chain of Pseudomonas syringae pv. syringae (cerasi) 435 lipopolysaccharide" -
Carbohydrate Research 212 (1991) 295-299
No abstract available
NCBI PubMed ID: 1720346Publication DOI: 10.1016/0008-6215(91)84069-qJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow
Methods: 13C NMR, methylation, GLC-MS, sugar analysis, GLC, Smith degradation, GPC
- Article ID: 2789
Ovod V, Ashorn P, Yakovleva L, Krohn K "Classification of Pseudomonas syringae with monoclonal antibodies against the core and O-side chains of the lipopolysaccharide" -
Phytopathology 85 (1995) 226-232
Journal NLM ID: 9427222Publisher: American Phytopathological Society
- Article ID: 3968
Zdorovenko GM, Zdorovenko EL "Pseudomonas syringae lipopolysaccharides: Immunochemical characteristics and structure as a basis for strain classification" -
Mikrobiologiia = Microbiology [Russian] 79(1) (2010) 47-57
Lipopolysaccharide (LPS) preparations of 34 Pseudomonas syringae strains of 19 pathovars were prepared by saline extraction from wet cells and purified by repeated ultracentrifugation. The preparations reacted with homologous O-antisera, obtained by rabbit immunization with heat-killed bacterial cells. Through inhibition of homologous reactions between LPS preparations of heterologous strains (enzyme immunoassay, EIA), it was established for the first time that high serological affinity between strains is observed only if their LPS contains O-specific polysaccharide chains (OPS) comprised of completely identical rather than partially similar units. The central linear part of the OPS was found to be serologically inert when shielded with side groups. Data on immunochemical characteristics of the LPS and OPS structure are analyzed in relation to the design of P. syringae classification scheme.
Lipopolysaccharide, structure, O-specific polysaccharide, Pseudomonas syringae, classification, immunochemistry
NCBI PubMed ID: 20411661Publication DOI: 10.1134/S0026261710010078Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: evelina@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kyiv, 03143 Ukraine
Methods: partial acid hydrolysis, EIA, serological methods, de-N-acetylation/deamination
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10. Compound ID: 1774
Structure type: oligomer
Contained glycoepitopes: IEDB_1394181,IEDB_145006,IEDB_145007,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 554
Bedini E, Carabellese A, Michela CM, De Castro C, Parrilli M "Synthesis of a D-rhamnose branched tetrasaccharide, repeating unit of the O-chain from Pseudomonas syringae pv. Syringae (cerasi) 435" -
Carbohydrate Research 339(11) (2004) 1907-1915
The first synthesis of a d-rhamnose branched tetrasaccharide, corresponding to the repeating unit of the O-chain from Pseudomonas syringae pv. cerasi 435, as methyl glycoside is reported. The approach used is based on the synthesis of an opportune building-block, that is the methyl 3-O-allyl-4-O-benzoyl-α-D-rhamnopyranoside, which was then converted into both a glycosyl acceptor and two different protected glycosyl trichloroacetimidate donors. Successive couplings of these three compounds afforded the target oligosaccharide. The reported synthesis is also useful to perform the oligomerization of the repeating unit
synthesis, repeating unit, O-chain, Pseudomonas cerasi, D-rhamnose, oligosaccharode
NCBI PubMed ID: 15261583Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: ebedini@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli 'Federico II', Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy
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11. Compound ID: 2908
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b-D-GlcpNAc-(1-4)-+
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-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_1394181,IEDB_141807,IEDB_144827,IEDB_145005,IEDB_145006,IEDB_145008,IEDB_145010,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1038
Müller P, Zähringer U, Rudolph K "Induced resistance by bacterial lipopolysaccharides (LPS)" -
Proceedings of Plant Pathogenic Bacteria, International Conference (9th : 1996 : Madras, India) (1998) 569-575
Lipopolysaccharides (LPS) were extracted from the Pseudomonas syringae pathovars: tomato race 1 (GSPB Nr. 1778), tomato race 0 (GSPB Nr. 1776), and glycinea race 9 (GSPB Nr. 1986) by the phenol/chloroform/petroleumbenzene-method (Galanos -et al 1979). The chemical analysis revealed 10% contamination by levan, a polyfructose, but also high amounts of KDO, PO4 (3-), GlcNAc and rhamnose. Chemical structure-analysis identified the O-specific chain, the-core region and lipid A. Lipid A was composed of the typical fatty acids of Pseudomonas such as 3-OH-C 10:0, C12:0, 3-OH C 12:0 and 2-OH C12:0. The structure of the O-chain corresponded to the one reported by Zdovorvenko et al. 1992, typical for Pseudomonas syringae pv. glycinea. Determination of the core-region has not been completely finished, but seems to show strong similarities to Pseudomonas aeruginosa and P. fluorescens. Induced resistance was studied in tomato and tobacco leaves. We investigated the role of whole LPS as well as its subunits O-chain and core region on induced resistance in compatible and incompatible systems. Resistance was induced by 50 jig LPS/ml in the incompatible system (LPS of Pseudomonas syringae pv. glycinea race 9 against P. s. pv. tomato race 1 in tomato cv. "Lyconorma"). Neither the O-specific chain nor the core region alone induced resistance. When similar experiments were performed by pretreatment with P.s. pv. tomato LPS followed by inoculation with P. s. pv. tomato (compatible system) resistance was not induced. Tobacco leaves were pretreated with 50-1000 uxj LPS/ml of P. s. pv. glycinea race 9 followed by inoculation with 108cfu/ml P. s. pv. glycinea race 9 48 h later. The pretreatment delayed appearance of the HR from 20 to 60 hrs after bacterial inoculation. The O-chain or the coreregion did not cause this effect. Further experiments have to show why the plants can differentiate between compatible and incompatible LPS, and whether the complete LPS-molecule is necessary for resistance induction or whether lipid A alone can cause this effect.
Lipopolysaccharide, lipopolysaccharides, LPS, structure, core, Bacterial, lipid A, induced, O polysaccharide, bacteria, Pseudomonas syringae, composition, resistance, plant, pathogenic bacteria, pathogenic, HR
Correspondence: PMUELLE@GWDG.DE
Editors: Mahadevan A
Institutions: Institut fur Phytopathologie and Pflanzenschutz der Universitat Gottingen Grisebachstr. 6, D-37077 Gottingen, Germany, Zentrum fur Medizin and Biowissenschaften, Borstel, Germany
Methods: sugar analysis
- Article ID: 1777
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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12. Compound ID: 2933
Structure type: polymer chemical repeating unit
Trivial name: D-rhamnan
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_1394181,IEDB_144827,IEDB_145005,IEDB_145006,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 1071
Ovod V, Rudolph K, Knirel YA, Krohn K "Immunochemical characterization of O polysaccharides composing the a-D-rhamnose backbone of lipopolysaccharide of Pseudomonas syringae and classification of bacteria into serogroups O1 and O2 with monoclonal antibodies" -
Journal of Bacteriology 178 (1996) 6459-6465
Murine monoclonal antibodies (MAbs) reacting with Pseudomonas syringae lipopolysaccharide (LPS) O polysaccharides (OPS) composed of tetra- and tri-α-D-rhamnose repeats in the backbone [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1-2)D-Rha(α1] and [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1] were generated and used for immunochemical analysis and for serological classification of the bacteria. A total of 195 of 358 P. syringae strains tested representing 21 pathovars were shown to share a common epitope, 1a, and were classified into serogroup O1. All strains with pathovars aptata, glycinea, japonica, phaseolicola, and pisi, most of the strains with pathovars atrofaciens and striafaciens, and half of the strains with pathovar syringae were classified into serotypes O1a', O1b, O1c, and O1d within serogroup O1. Serogroup-specific epitope 1a was inferred to be related to the (α1-2)D-Rha(α1-3) site of the OPS backbone. The serotype-specific epitopes 1b, 1c, 1d, and 1a' were inferred as relating to the immunodominant lateral (α1-3)D-Rha, (β1-4)D-GlcNAc, and (α1-4)D-Fuc substituents and backbone-located site (α1-3)D-Rha(α1-2), respectively, of OPSs that share the common tetra-D-rhamnose repeats in the backbone. A total of 7.3% of the strains studied, all with pathovars morsprunorum and lapsa, were classified as serotypes O2a and O2d within serogroup 02. Serotype-specific epitope 2a was inferred as being related to the backbone-located site D-Rha(α1-3)D-Rha and epitope 2d to the immunodominant lateral (α1-4)D-Fuc residue of OPS consisting of tri-D-rhamnose repeats in the backbone. Epitope 2d alternated with 2a within the same LPS molecule and did not cross-react with epitope 1d. Serotypes O2a and O2d were observed in some strains correlating with the coexpression of the two chemotypes of OPS by the same strain. The serogroup O1-specific MAb Ps1a reacted weakly but definitely with all strains from serogroup 02. We propose serological formulas for serogroups O1 and 02 as well as for individual strains within these serogroups.
Lipopolysaccharide, LPS, characterization, polysaccharide, polysaccharides, Pseudomonas, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, serogroup, backbone, immunochemical, Pseudomonas syringae, classification, D-rhamnose
NCBI PubMed ID: 8932301Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Ltvlov@uta.fi
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Tampere, Finland, Department of Microbiology and Immunology, University of Kiev, Kiev, Ukraine, Institut fur Pflanzenpathologie und Pflanzenschutz der Georg-August-Universitat, Gottingen, Germany
Methods: serological methods
- Article ID: 1073
Ovod V, Knirel Y, Krohn K "Demonstration of the immunochemical diversity of O-chains of lipopolysaccharide of Pseudomonas syringae and inferring of the serogroup- and serotype-specific epitopes with monoclonal antibodies" -
Proceedings of International Conference on Pseudomonas syringae Pathovars and Related Pathogens (5th : 1995 : Berlin, Germany) (1997) Vol. 9, 532-537
Using serogroup- and serotyppe-specific murine monoclonal antibodies (MAbs) to Pseudomonas syringae lipopolysacharide (LPS) O-polysaccharides (OPS) (=O chains) with elucidated primary chemical structure of the O-repeating units, a rather high diversity of the OPS-related epitopes was demonstrated and most of them were inferred. The immunogenic properties of the O-serogroup- and O-serotype-specific epitopes were shown to depend on the nature and the number of sugar residues in the O-repeat as well as on the arrangement of the monosaccharides and the mode of linkages between them.
Lipopolysaccharide, LPS, structure, strain, Pseudomonas, chain, group, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, epitopes, O-polysaccharide, serogroup, immunochemical, O-chain, pathogen, pathogens, pathovar, Pseudomonas syringae, classification, diversity, serotype-specific
Publisher: Kluwer Academic Publishers, The Netherlands
Correspondence: knirel@ioc.ac.ru
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead DE, Vivian A, von Kietzell J
Institutions: Institute of Medical Technology, University of Tampere, Tampere, Finland, N.D. Zelinsy Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1074
Ovod V, Knirel YA, Samson R, Krohn K "Immunochemical characterization and taxonomic evaluation of the O polysaccharides of the lipopolysaccharides of Pseudomonas syringae serogroup O1 strains" -
Journal of Bacteriology 181(22) (1999) 6937-6947
The O polysaccharide (OPS) of the lipopolysaccharide (LPS) of Pseudomonas syringae pv. atrofaciens IMV 7836 and some other strains that are classified in serogroup O1 was shown to be a novel linear α-D-rhamnan with the tetrasaccharide O repeat →3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→2)-α-D-Rhap-(1→ (chemotype 1A). The same α-D-rhamnan serves as the backbone in branched OPSs with lateral (α1→3)-linked D-Rhap, (β1→4)-linked D-GlcpNAc, and (α1→4)-linked D-Fucf residues (chemotypes 1B, 1C, and 1D, respectively). Strains of chemotype 1C demonstrated variations resulting in a decrease of the degree of substitution of the backbone 1A with the lateral D-GlcNAc residue (chemotype 1C-1A), which may be described as branched regular <→ branched irregular → linear OPS structure alterations (1C <→ 1C-1A → 1A). Based on serological data, chemotype 1D was suggested to undergo a 1D <→ 1D-1A alteration, whereas chemotype 1B showed no alteration. A number of OPS backbone-specific monoclonal antibodies (MAbs), Ps(1-2)a, Ps(1-2)a(1), Ps1a, Ps1a(1), and Ps1a(2), as well as MAbs Ps1b, Ps1c, Ps1c(1), Ps1d, Ps(1-2)d, and Ps(1-2)d(1) specific to epitopes related to the lateral sugar substituents of the OPSs, were produced against P. syringae serogroup O1 strains. By using MAbs, some specific epitopes were inferred, serogroup O1 strains were serotyped in more detail, and thus, the serological classification scheme of P. syringae was improved. Screening with MAbs of about 800 strains representing all 56 known P. syringae pathovars showed that the strains classified in serogroup O1 were found among 15 pathovars and the strains with the linear OPSs of chemotype 1A were found among 9 of the 15 pathovars. A possible role for the LPS of P. syringae and related pseudomonads as a phylogenetic marker is discussed.
Lipopolysaccharide, lipopolysaccharides, LPS, strain, structural, characterization, polysaccharide, polysaccharides, Pseudomonas, antibody, epitope, monoclonal, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, serogroup, evaluation, backbone, immunochemical, Pseudomonas syringae, classification, linear, taxonomic, D-rhamnose
NCBI PubMed ID: 10559159Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Ltvlov@uta.fi
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Tampere, Finland, Pathologie Vegetale, Institut National de la Recherche Agronomique, Beaucouze Cedex, France
Methods: NMR
- Article ID: 1313
Zdorovenko EL, Ovod V, Zatonsky GV, Shashkov AS, Kocharova NA, Knirel YA "Location of the O-methyl groups in the O polysaccharide of Pseudomonas syringae pv. phaseolicola" -
Carbohydrate Research 330(4) (2001) 505-510
The O-methylation pattern of the O polysaccharide (OPS) of the lipopolysaccharide of Pseudomonas syringae pv. phaseolicola GSPB 1552 was revealed by methylation (CD3I) analysis, Smith degradation, and NMR spectroscopy. Together with the major O repeats consisting of D-rhamnopyranose (D-Rhap) and D-fucofuranose (D-Fucf), there are minor repeats (approximately 30%) containing 3-O-methyl-D-rhamnose (D-acofriose), which is 2-substituted in the interior repeats and occupies the terminal non-reducing end of the OPS. It was suggested that the methylated O repeats are linked to each other nearby the non-reducing end of the OPS and that the 'biological' O repeat of the OPS has the following structure: [molecular structure: see text]
Lipopolysaccharide, Pseudomonas syringae, O-polysaccharides, O-methylation, phytopathogens
NCBI PubMed ID: 11269402Publication DOI: 10.1016/S0008-6215(01)00005-2Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: Institute of Medical Technology, University of Tampere, Tampere, Finland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Institute of Medical Technology, University of Tampere, Tampere, Finalnd
Methods: NMR-2D, methylation, NMR, Smith degradation
- Article ID: 1452
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 1465
Knirel YA, Zdorovenko GM "Structures of O-polysaccharide chains of lipopolysaccharides as the basis for classification of Pseudomonas syringae and related strains" -
Book: Pseudomonas Syringae Pathovars and Related Pathogens (series: Developments in Plant Pathology) (1997) 475-480
The O-polysaccharides of various serogroups of P. syringae were found to have similar structures with the main chain of a rhamnan which may carry a monosaccharide side chain of D-rhamnose, D-fucose, 2-acetamido-2-deoxy-D-glucose or 3-acetamido-3,6-dideoxy-D-galactose. The relationship between the serological specificity and the host-plant specificity of P. syringae and the structures of the O-polysaccharides is discussed.
Lipopolysaccharide, structure, O-antigen, O-polysaccharide, serological specificity, Pseudomonas syringae, Serogrouping, Host-plant specificity
Publication DOI: 10.1007/978-94-011-5472-7_85Publisher: Springer Netherlands
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead D, Vivian A, von Kietzell J
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Leninsky Pr. 47, Moscow B-334, Russia, D.K. Zabolotny Institute of Microbiology and Virology, Zabolotnogo 154, Kiev-143, Ukraine
- Article ID: 1853
Knirel YA, Zdorovenko GM, Shashkov AS, Gubanova NY, Yakovleva LM, Gvozdyak RI "Antigenic polysaccharides of bacteria. 27. Structure of the O-specific polysaccharide chain of lipopolysaccharides from Pseudomonas syringae pvs atrofaciens 2399, phaseolicola 120a and Pseudomonas holci 8299, belonging to serogroup VI" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14(1) (1988) 92-99
Lipopolysaccharides from Pseudomonas syringae pvs atrofaciens 2399. phaseolicola 120a and Pseudomonas holci 8299, belonging to serogroup VI. possess an identical polysaccharide chain composed of D-rhamnose and D-fucose. On the hasis of methylation, partial acid hydrolysis, 1H- and 13C-NMR data, it was concluded that the backbone of the polysaccharide represents D-rhamnan built up of tetrasaccharide repeating units and α-D-fucofuranose residues are attached to the backbone as the monosaccharide branches. The following structure of the repeating unit is established: (Formula: see text).
NCBI PubMed ID: 2454626Journal NLM ID: 7804941WWW link: http://www.rjbc.ru/arc/14/1/0092-0099.pdfPublisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR
- Article ID: 2789
Ovod V, Ashorn P, Yakovleva L, Krohn K "Classification of Pseudomonas syringae with monoclonal antibodies against the core and O-side chains of the lipopolysaccharide" -
Phytopathology 85 (1995) 226-232
Journal NLM ID: 9427222Publisher: American Phytopathological Society
- Article ID: 3968
Zdorovenko GM, Zdorovenko EL "Pseudomonas syringae lipopolysaccharides: Immunochemical characteristics and structure as a basis for strain classification" -
Mikrobiologiia = Microbiology [Russian] 79(1) (2010) 47-57
Lipopolysaccharide (LPS) preparations of 34 Pseudomonas syringae strains of 19 pathovars were prepared by saline extraction from wet cells and purified by repeated ultracentrifugation. The preparations reacted with homologous O-antisera, obtained by rabbit immunization with heat-killed bacterial cells. Through inhibition of homologous reactions between LPS preparations of heterologous strains (enzyme immunoassay, EIA), it was established for the first time that high serological affinity between strains is observed only if their LPS contains O-specific polysaccharide chains (OPS) comprised of completely identical rather than partially similar units. The central linear part of the OPS was found to be serologically inert when shielded with side groups. Data on immunochemical characteristics of the LPS and OPS structure are analyzed in relation to the design of P. syringae classification scheme.
Lipopolysaccharide, structure, O-specific polysaccharide, Pseudomonas syringae, classification, immunochemistry
NCBI PubMed ID: 20411661Publication DOI: 10.1134/S0026261710010078Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: evelina@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kyiv, 03143 Ukraine
Methods: partial acid hydrolysis, EIA, serological methods, de-N-acetylation/deamination
Expand this compound
Collapse this compound
13. Compound ID: 2978
|
a-D-Rhap-(1-3)-+
|
-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: D-rhamnan
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_1394181,IEDB_144827,IEDB_144828,IEDB_145005,IEDB_145006,IEDB_145007,IEDB_145010
The structure is contained in the following publication(s):
- Article ID: 1071
Ovod V, Rudolph K, Knirel YA, Krohn K "Immunochemical characterization of O polysaccharides composing the a-D-rhamnose backbone of lipopolysaccharide of Pseudomonas syringae and classification of bacteria into serogroups O1 and O2 with monoclonal antibodies" -
Journal of Bacteriology 178 (1996) 6459-6465
Murine monoclonal antibodies (MAbs) reacting with Pseudomonas syringae lipopolysaccharide (LPS) O polysaccharides (OPS) composed of tetra- and tri-α-D-rhamnose repeats in the backbone [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1-2)D-Rha(α1] and [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1] were generated and used for immunochemical analysis and for serological classification of the bacteria. A total of 195 of 358 P. syringae strains tested representing 21 pathovars were shown to share a common epitope, 1a, and were classified into serogroup O1. All strains with pathovars aptata, glycinea, japonica, phaseolicola, and pisi, most of the strains with pathovars atrofaciens and striafaciens, and half of the strains with pathovar syringae were classified into serotypes O1a', O1b, O1c, and O1d within serogroup O1. Serogroup-specific epitope 1a was inferred to be related to the (α1-2)D-Rha(α1-3) site of the OPS backbone. The serotype-specific epitopes 1b, 1c, 1d, and 1a' were inferred as relating to the immunodominant lateral (α1-3)D-Rha, (β1-4)D-GlcNAc, and (α1-4)D-Fuc substituents and backbone-located site (α1-3)D-Rha(α1-2), respectively, of OPSs that share the common tetra-D-rhamnose repeats in the backbone. A total of 7.3% of the strains studied, all with pathovars morsprunorum and lapsa, were classified as serotypes O2a and O2d within serogroup 02. Serotype-specific epitope 2a was inferred as being related to the backbone-located site D-Rha(α1-3)D-Rha and epitope 2d to the immunodominant lateral (α1-4)D-Fuc residue of OPS consisting of tri-D-rhamnose repeats in the backbone. Epitope 2d alternated with 2a within the same LPS molecule and did not cross-react with epitope 1d. Serotypes O2a and O2d were observed in some strains correlating with the coexpression of the two chemotypes of OPS by the same strain. The serogroup O1-specific MAb Ps1a reacted weakly but definitely with all strains from serogroup 02. We propose serological formulas for serogroups O1 and 02 as well as for individual strains within these serogroups.
Lipopolysaccharide, LPS, characterization, polysaccharide, polysaccharides, Pseudomonas, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, serogroup, backbone, immunochemical, Pseudomonas syringae, classification, D-rhamnose
NCBI PubMed ID: 8932301Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Ltvlov@uta.fi
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Tampere, Finland, Department of Microbiology and Immunology, University of Kiev, Kiev, Ukraine, Institut fur Pflanzenpathologie und Pflanzenschutz der Georg-August-Universitat, Gottingen, Germany
Methods: serological methods
- Article ID: 1073
Ovod V, Knirel Y, Krohn K "Demonstration of the immunochemical diversity of O-chains of lipopolysaccharide of Pseudomonas syringae and inferring of the serogroup- and serotype-specific epitopes with monoclonal antibodies" -
Proceedings of International Conference on Pseudomonas syringae Pathovars and Related Pathogens (5th : 1995 : Berlin, Germany) (1997) Vol. 9, 532-537
Using serogroup- and serotyppe-specific murine monoclonal antibodies (MAbs) to Pseudomonas syringae lipopolysacharide (LPS) O-polysaccharides (OPS) (=O chains) with elucidated primary chemical structure of the O-repeating units, a rather high diversity of the OPS-related epitopes was demonstrated and most of them were inferred. The immunogenic properties of the O-serogroup- and O-serotype-specific epitopes were shown to depend on the nature and the number of sugar residues in the O-repeat as well as on the arrangement of the monosaccharides and the mode of linkages between them.
Lipopolysaccharide, LPS, structure, strain, Pseudomonas, chain, group, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, epitopes, O-polysaccharide, serogroup, immunochemical, O-chain, pathogen, pathogens, pathovar, Pseudomonas syringae, classification, diversity, serotype-specific
Publisher: Kluwer Academic Publishers, The Netherlands
Correspondence: knirel@ioc.ac.ru
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead DE, Vivian A, von Kietzell J
Institutions: Institute of Medical Technology, University of Tampere, Tampere, Finland, N.D. Zelinsy Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1074
Ovod V, Knirel YA, Samson R, Krohn K "Immunochemical characterization and taxonomic evaluation of the O polysaccharides of the lipopolysaccharides of Pseudomonas syringae serogroup O1 strains" -
Journal of Bacteriology 181(22) (1999) 6937-6947
The O polysaccharide (OPS) of the lipopolysaccharide (LPS) of Pseudomonas syringae pv. atrofaciens IMV 7836 and some other strains that are classified in serogroup O1 was shown to be a novel linear α-D-rhamnan with the tetrasaccharide O repeat →3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→2)-α-D-Rhap-(1→ (chemotype 1A). The same α-D-rhamnan serves as the backbone in branched OPSs with lateral (α1→3)-linked D-Rhap, (β1→4)-linked D-GlcpNAc, and (α1→4)-linked D-Fucf residues (chemotypes 1B, 1C, and 1D, respectively). Strains of chemotype 1C demonstrated variations resulting in a decrease of the degree of substitution of the backbone 1A with the lateral D-GlcNAc residue (chemotype 1C-1A), which may be described as branched regular <→ branched irregular → linear OPS structure alterations (1C <→ 1C-1A → 1A). Based on serological data, chemotype 1D was suggested to undergo a 1D <→ 1D-1A alteration, whereas chemotype 1B showed no alteration. A number of OPS backbone-specific monoclonal antibodies (MAbs), Ps(1-2)a, Ps(1-2)a(1), Ps1a, Ps1a(1), and Ps1a(2), as well as MAbs Ps1b, Ps1c, Ps1c(1), Ps1d, Ps(1-2)d, and Ps(1-2)d(1) specific to epitopes related to the lateral sugar substituents of the OPSs, were produced against P. syringae serogroup O1 strains. By using MAbs, some specific epitopes were inferred, serogroup O1 strains were serotyped in more detail, and thus, the serological classification scheme of P. syringae was improved. Screening with MAbs of about 800 strains representing all 56 known P. syringae pathovars showed that the strains classified in serogroup O1 were found among 15 pathovars and the strains with the linear OPSs of chemotype 1A were found among 9 of the 15 pathovars. A possible role for the LPS of P. syringae and related pseudomonads as a phylogenetic marker is discussed.
Lipopolysaccharide, lipopolysaccharides, LPS, strain, structural, characterization, polysaccharide, polysaccharides, Pseudomonas, antibody, epitope, monoclonal, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, serogroup, evaluation, backbone, immunochemical, Pseudomonas syringae, classification, linear, taxonomic, D-rhamnose
NCBI PubMed ID: 10559159Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Ltvlov@uta.fi
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Tampere, Finland, Pathologie Vegetale, Institut National de la Recherche Agronomique, Beaucouze Cedex, France
Methods: NMR
- Article ID: 1452
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 1465
Knirel YA, Zdorovenko GM "Structures of O-polysaccharide chains of lipopolysaccharides as the basis for classification of Pseudomonas syringae and related strains" -
Book: Pseudomonas Syringae Pathovars and Related Pathogens (series: Developments in Plant Pathology) (1997) 475-480
The O-polysaccharides of various serogroups of P. syringae were found to have similar structures with the main chain of a rhamnan which may carry a monosaccharide side chain of D-rhamnose, D-fucose, 2-acetamido-2-deoxy-D-glucose or 3-acetamido-3,6-dideoxy-D-galactose. The relationship between the serological specificity and the host-plant specificity of P. syringae and the structures of the O-polysaccharides is discussed.
Lipopolysaccharide, structure, O-antigen, O-polysaccharide, serological specificity, Pseudomonas syringae, Serogrouping, Host-plant specificity
Publication DOI: 10.1007/978-94-011-5472-7_85Publisher: Springer Netherlands
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead D, Vivian A, von Kietzell J
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Leninsky Pr. 47, Moscow B-334, Russia, D.K. Zabolotny Institute of Microbiology and Virology, Zabolotnogo 154, Kiev-143, Ukraine
- Article ID: 1777
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1854
Knirel YA, Zdorovenko GM, Yakovleva LM, Shashkov AS, Solyanik LP, Zakharova IY "Antigenic polysaccharides of bacteria. 28. Structure of O-specific chain of lipopolysaccharide of Pseudomonas syringae pv. atrofaciens K-1025 and Pseudomonas holci 90a (serogroup II)" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14(2) (1988) 166-171
Lipopolysaccharides of serologically related strains of Pseudomonas syringae pv. atrofaciens K-1025 and Pseudomonas holci 90a possess the identical O-specific polysaccharide chains, representing a homopolymer of D-rhamnose. On the basis of methylation, partial and complete Smith degradation, and analysis by 1H- and 13C-NMR-spectroscopy, it was concluded that the repeating unit of the polysaccharide is a branched pentasaccharide of the following structure: (formula; see text)
NCBI PubMed ID: 2454627Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR, methylation, sugar analysis, Smith degradation
- Article ID: 2188
Vinogradov EV, Shashkov AS, Knirel YA, Zdorovenko GM, Solyanik LP, Gvozdyak RI "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide chain of Pseudomonas syringae pv. syringae (cerasi) 435 lipopolysaccharide" -
Carbohydrate Research 212 (1991) 295-299
No abstract available
NCBI PubMed ID: 1720346Publication DOI: 10.1016/0008-6215(91)84069-qJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow
Methods: 13C NMR, methylation, GLC-MS, sugar analysis, GLC, Smith degradation, GPC
- Article ID: 2234
Lipkind GM, Shashkov AS, Nifant'ev NE, Kochetkov NK "Computer-assisted analysis of the structure of regular branched polysaccharides containing 2,3-disubstituted rhamnopyranose and mannopyranose residues on the basis of 13C NMR" -
Carbohydrate Research 237 (1992) 11-22
A computer-assisted approach to the analysis of the structure of branched polysaccharides that contain 2,3-di-O-glycosylated α-rhamnopyranose and α-mannopyranose residues is based on evaluation of the 13C NMR spectra, using glycosylation effects and their deviations from additivity (delta delta values) at the branch points. This approach, in combination with monosaccharide and methylation analysis data, has been verified on a series of bacterial polysaccharides of known structure
NCBI PubMed ID: 1284111Publication DOI: 10.1016/S0008-6215(92)84229-LJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
Methods: 13C NMR
- Article ID: 2789
Ovod V, Ashorn P, Yakovleva L, Krohn K "Classification of Pseudomonas syringae with monoclonal antibodies against the core and O-side chains of the lipopolysaccharide" -
Phytopathology 85 (1995) 226-232
Journal NLM ID: 9427222Publisher: American Phytopathological Society
- Article ID: 3313
Zdorovenko GM, Zdorovenko EL, Varbanets LD "Composition, structure, and biological properties of lipopolysaccharides from different strains of Pseudomonas syringae pv. atrofaciens" -
Mikrobiologiia = Microbiology [Russian] 76(6) (2007) 683-697
The composition, structure, and certain biological properties of lipopolysaccharides (LPS) isolated from six strains of bacteria Pseudomonas syringae pv.atrofaciens pathogenic for grain-crops (wheat, rye) are presented. The LPS-protein complexes were isolated by a sparing procedure (extraction from microbial cells with a weak salt solution). They reacted with the homologous O sera and contained one to three antigenic determinants. Against the cells of warm-blooded animals (mice, humans) they exhibited the biological activity typical of endotoxins (stimulation of cytokine production, mitogenetic activity, etc.). The LCD of the biovar type strain was highly toxic to mice sensitized with D-galactosamine. The structural components of LPS macromolecules obtained by mild acidic degradation were characterized: lipid A, core oligosaccharide, and O-specific polysaccharide (OPS). Fatty acids 3-HO-C10:0, C12:0, 2-HO-C12:0, 3-HO-C12:0, C16:0, C16:1, C18:0, and C18:1 were identified in lipid A of all the strains, as well as the components of the hydrophilic part: glucosamine (GlcN), ethanolamine (EtN), phosphate, and phosphoethanolamine (EtN-P). In the core LPS, glucose (Glc), rhamnose(Rha), L-glycero-D-manno-heptose (Hep), GlcN, galactosamine (GalN), 2-keto-3-deoxy-D-mannooctonoi acid (KDO), alanine (Ala), and phosphate were present. The O chain of all the strains consisted of repeated elements containing a linear chain of three to four L- (two strains) or D-Rha (four strains) residues supplemented with a single residue of 3-acetamido-3,6-dideoxy-D-galactose (D-Fucp3Nac), N-acetyl-D-glucosamine(D-GlcpNAc), D-fucose (D-Fucf), or D-Rhap (strain-dependent) as a side substituent. In different strains the substitution position for Rha residues in the repeated components of the major rhamnan chain was also different.One strain exhibited a unique type of O-chain heterogeneity. Immunochemical investigation of the LPS antigenic properties revealed the absence of close serological relations between the strains of one pathovar; this finding correlates with the differences in their OPS structure. Resemblance between the investigated strains and other P.syringae strains with similar LPS structures was revealed. The results of LPS analysis indicate the absence of correlation between the OPS structure and the pathovar affiliation of the strains.
Lipopolysaccharide, structure, lipid A, core oligosaccharide, O-specific polysaccharide, biological activity, immunochemistry, Pseudomonas syringae pv.atrofaciens
NCBI PubMed ID: 18297868Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: alz@i.com.ua; evelina@ioc.ac.ru
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
Methods: 13C NMR, 1H NMR, GLC-MS, sugar analysis, serological methods
- Article ID: 3968
Zdorovenko GM, Zdorovenko EL "Pseudomonas syringae lipopolysaccharides: Immunochemical characteristics and structure as a basis for strain classification" -
Mikrobiologiia = Microbiology [Russian] 79(1) (2010) 47-57
Lipopolysaccharide (LPS) preparations of 34 Pseudomonas syringae strains of 19 pathovars were prepared by saline extraction from wet cells and purified by repeated ultracentrifugation. The preparations reacted with homologous O-antisera, obtained by rabbit immunization with heat-killed bacterial cells. Through inhibition of homologous reactions between LPS preparations of heterologous strains (enzyme immunoassay, EIA), it was established for the first time that high serological affinity between strains is observed only if their LPS contains O-specific polysaccharide chains (OPS) comprised of completely identical rather than partially similar units. The central linear part of the OPS was found to be serologically inert when shielded with side groups. Data on immunochemical characteristics of the LPS and OPS structure are analyzed in relation to the design of P. syringae classification scheme.
Lipopolysaccharide, structure, O-specific polysaccharide, Pseudomonas syringae, classification, immunochemistry
NCBI PubMed ID: 20411661Publication DOI: 10.1134/S0026261710010078Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: evelina@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kyiv, 03143 Ukraine
Methods: partial acid hydrolysis, EIA, serological methods, de-N-acetylation/deamination
Expand this compound
Collapse this compound
14. Compound ID: 2979
|
b-D-GlcpNAc-(1-4)-+
|
-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: D-rhamnan
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_1394181,IEDB_141807,IEDB_144827,IEDB_144829,IEDB_145005,IEDB_145006,IEDB_145008,IEDB_145010,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1071
Ovod V, Rudolph K, Knirel YA, Krohn K "Immunochemical characterization of O polysaccharides composing the a-D-rhamnose backbone of lipopolysaccharide of Pseudomonas syringae and classification of bacteria into serogroups O1 and O2 with monoclonal antibodies" -
Journal of Bacteriology 178 (1996) 6459-6465
Murine monoclonal antibodies (MAbs) reacting with Pseudomonas syringae lipopolysaccharide (LPS) O polysaccharides (OPS) composed of tetra- and tri-α-D-rhamnose repeats in the backbone [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1-2)D-Rha(α1] and [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1] were generated and used for immunochemical analysis and for serological classification of the bacteria. A total of 195 of 358 P. syringae strains tested representing 21 pathovars were shown to share a common epitope, 1a, and were classified into serogroup O1. All strains with pathovars aptata, glycinea, japonica, phaseolicola, and pisi, most of the strains with pathovars atrofaciens and striafaciens, and half of the strains with pathovar syringae were classified into serotypes O1a', O1b, O1c, and O1d within serogroup O1. Serogroup-specific epitope 1a was inferred to be related to the (α1-2)D-Rha(α1-3) site of the OPS backbone. The serotype-specific epitopes 1b, 1c, 1d, and 1a' were inferred as relating to the immunodominant lateral (α1-3)D-Rha, (β1-4)D-GlcNAc, and (α1-4)D-Fuc substituents and backbone-located site (α1-3)D-Rha(α1-2), respectively, of OPSs that share the common tetra-D-rhamnose repeats in the backbone. A total of 7.3% of the strains studied, all with pathovars morsprunorum and lapsa, were classified as serotypes O2a and O2d within serogroup 02. Serotype-specific epitope 2a was inferred as being related to the backbone-located site D-Rha(α1-3)D-Rha and epitope 2d to the immunodominant lateral (α1-4)D-Fuc residue of OPS consisting of tri-D-rhamnose repeats in the backbone. Epitope 2d alternated with 2a within the same LPS molecule and did not cross-react with epitope 1d. Serotypes O2a and O2d were observed in some strains correlating with the coexpression of the two chemotypes of OPS by the same strain. The serogroup O1-specific MAb Ps1a reacted weakly but definitely with all strains from serogroup 02. We propose serological formulas for serogroups O1 and 02 as well as for individual strains within these serogroups.
Lipopolysaccharide, LPS, characterization, polysaccharide, polysaccharides, Pseudomonas, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, serogroup, backbone, immunochemical, Pseudomonas syringae, classification, D-rhamnose
NCBI PubMed ID: 8932301Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Ltvlov@uta.fi
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Tampere, Finland, Department of Microbiology and Immunology, University of Kiev, Kiev, Ukraine, Institut fur Pflanzenpathologie und Pflanzenschutz der Georg-August-Universitat, Gottingen, Germany
Methods: serological methods
- Article ID: 1073
Ovod V, Knirel Y, Krohn K "Demonstration of the immunochemical diversity of O-chains of lipopolysaccharide of Pseudomonas syringae and inferring of the serogroup- and serotype-specific epitopes with monoclonal antibodies" -
Proceedings of International Conference on Pseudomonas syringae Pathovars and Related Pathogens (5th : 1995 : Berlin, Germany) (1997) Vol. 9, 532-537
Using serogroup- and serotyppe-specific murine monoclonal antibodies (MAbs) to Pseudomonas syringae lipopolysacharide (LPS) O-polysaccharides (OPS) (=O chains) with elucidated primary chemical structure of the O-repeating units, a rather high diversity of the OPS-related epitopes was demonstrated and most of them were inferred. The immunogenic properties of the O-serogroup- and O-serotype-specific epitopes were shown to depend on the nature and the number of sugar residues in the O-repeat as well as on the arrangement of the monosaccharides and the mode of linkages between them.
Lipopolysaccharide, LPS, structure, strain, Pseudomonas, chain, group, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, epitopes, O-polysaccharide, serogroup, immunochemical, O-chain, pathogen, pathogens, pathovar, Pseudomonas syringae, classification, diversity, serotype-specific
Publisher: Kluwer Academic Publishers, The Netherlands
Correspondence: knirel@ioc.ac.ru
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead DE, Vivian A, von Kietzell J
Institutions: Institute of Medical Technology, University of Tampere, Tampere, Finland, N.D. Zelinsy Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1320
Zdorovenko GM, Shashkov AS, Zdorovenko EL, Kocharova NA, Yakovleva LM, Knirel YA, Rudolph K "Characterization of the lipopolysaccharide and structure of the O-specific polysaccharide of the bacterium Pseudomonas syringae pv. atrofaciens IMV 948" -
Biochemistry (Moscow) 66(4) (2001) 369-377
Lipopolysaccharide (LPS) was isolated from the phytopathogenic bacterium Pseudomonas syringae pv. atrofaciens IMV 948 by mild extraction of the microbial cells with saline, and the properties, composition, and structure of the LPS were studied. The LPS showed low toxicity in D- galactosamine-sensitized mice and low biological activity in plants. Structural components of LPS--lipid A, core oligosaccharide, and O-specific polysaccharide (OPS)--were obtained by mild acid degradation and characterized. The lipid A contained fatty acids 3-HO-C10:0, C12:0, 2-HO-C12:0, 3-HO-C12:0, C16:0, C16:1, C18:0, and C18:1, as well as components of the hydrophilic moiety: GlcN, ethanolamine, phosphate, and phosphoethanolamine. The LPS core contained components typical of pseudomonads: glucose, rhamnose (Rha), L-glycero-D-manno-heptose, GlcN, GalN, 2-keto-3-deoxy-D-manno-octonic acid, alanine, and phosphate. The OPS consisted of L-Rha and D-GlcNAc in the ratio 4 : 1 and was structurally heterogeneous. The main pentasaccharide repeating unit of the OPS has the following structure: [structure see text]. Immunochemical studies showed that P. syringae pv. atrofaciens IMV 948 is serologically separate from other P. syringae strains, including those that have structurally similar OPS
Lipopolysaccharide, structure, Pseudomonas syringae, composition, immunochemistry, omposition
NCBI PubMed ID: 11403642Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: zdorov@i.kiev.ua
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, 252143, Ukraine, Institut fur Pflazenpathologie und Pfalnzenschutz, Georg-August-Universitat, Gottingen, 37077, Germany
Methods: NMR-2D, methylation, NMR
- Article ID: 1452
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 1465
Knirel YA, Zdorovenko GM "Structures of O-polysaccharide chains of lipopolysaccharides as the basis for classification of Pseudomonas syringae and related strains" -
Book: Pseudomonas Syringae Pathovars and Related Pathogens (series: Developments in Plant Pathology) (1997) 475-480
The O-polysaccharides of various serogroups of P. syringae were found to have similar structures with the main chain of a rhamnan which may carry a monosaccharide side chain of D-rhamnose, D-fucose, 2-acetamido-2-deoxy-D-glucose or 3-acetamido-3,6-dideoxy-D-galactose. The relationship between the serological specificity and the host-plant specificity of P. syringae and the structures of the O-polysaccharides is discussed.
Lipopolysaccharide, structure, O-antigen, O-polysaccharide, serological specificity, Pseudomonas syringae, Serogrouping, Host-plant specificity
Publication DOI: 10.1007/978-94-011-5472-7_85Publisher: Springer Netherlands
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead D, Vivian A, von Kietzell J
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Leninsky Pr. 47, Moscow B-334, Russia, D.K. Zabolotny Institute of Microbiology and Virology, Zabolotnogo 154, Kiev-143, Ukraine
- Article ID: 1834
Knirel YA, Zdorovenko GM, Dashunin VM, Yakovleva LM, Shashkov AS, Zakharova IY, Gvozdyak RI, Kochetkov NK "Antigenic polysaccharides of bacteria. 15. Structure of the repeating unit of O-specific polysaccharide chain of Pseudomonas wieringae lipopolysaccharide" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 12(9) (1986) 1253-1262
No abstract available
Journal NLM ID: 7804941WWW link: http://www.rjbc.ru/arc/12/9/1253-1262.pdfPublisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR
- Article ID: 2789
Ovod V, Ashorn P, Yakovleva L, Krohn K "Classification of Pseudomonas syringae with monoclonal antibodies against the core and O-side chains of the lipopolysaccharide" -
Phytopathology 85 (1995) 226-232
Journal NLM ID: 9427222Publisher: American Phytopathological Society
- Article ID: 5242
Zdorovenko EL, Besarab NV, Shashkov AS, Novik GI, Shirokov AA, Burov AM, Knirel YA "Investigation of O-polysaccharides from bacterial strains of Pseudomonas genus as potential receptors of bacteriophage BIM BV-45." -
International Journal of Biological Macromolecules 118 (2018) 1065-1072
The structure of potential bacteriophage receptors located on cell walls of Gram-negative bacteria deposited at Belarusian collection of microorganisms was investigated. Studies by 1D and 2D 1H and 13C NMR spectroscopy enabled to elucidate the structure of the O-specific polysaccharides (OPS) constituting lipopolysaccharide (LPS) of some Pseudomonas species. The capacity of bacteriophage to adsorb to LPS molecules was tested.
Pseudomonas, NMR spectroscopy, Bacteriophages, electron microscopy, Adsorption, O-polysaccharides (OPS)
Publication DOI: 10.1016/j.ijbiomac.2018.06.165Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: zdorovenkoe@mail.ru
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology, National Academy of Sciences of Belarus, 220141 Minsk, Belarus, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 410049, Saratov, Russian Federation
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, mild acid hydrolysis, GC, GPC, analysis of bacteriophage morphology, analysis of the bacteriophages adsorption
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15. Compound ID: 2980
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a-D-Fucp-(1-4)-+
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-3)-a-D-Rhap-(1-3)-a-D-Rhap-(1-2)-a-D-Rhap-(1-2)-a-D-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115015,IEDB_1394181,IEDB_142489,IEDB_144827,IEDB_145005,IEDB_145006,IEDB_145009,IEDB_145010,IEDB_149135,SB_86
The structure is contained in the following publication(s):
- Article ID: 1071
Ovod V, Rudolph K, Knirel YA, Krohn K "Immunochemical characterization of O polysaccharides composing the a-D-rhamnose backbone of lipopolysaccharide of Pseudomonas syringae and classification of bacteria into serogroups O1 and O2 with monoclonal antibodies" -
Journal of Bacteriology 178 (1996) 6459-6465
Murine monoclonal antibodies (MAbs) reacting with Pseudomonas syringae lipopolysaccharide (LPS) O polysaccharides (OPS) composed of tetra- and tri-α-D-rhamnose repeats in the backbone [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1-2)D-Rha(α1] and [3)D-Rha(α1-3)D-Rha(α1-2)D-Rha(α1] were generated and used for immunochemical analysis and for serological classification of the bacteria. A total of 195 of 358 P. syringae strains tested representing 21 pathovars were shown to share a common epitope, 1a, and were classified into serogroup O1. All strains with pathovars aptata, glycinea, japonica, phaseolicola, and pisi, most of the strains with pathovars atrofaciens and striafaciens, and half of the strains with pathovar syringae were classified into serotypes O1a', O1b, O1c, and O1d within serogroup O1. Serogroup-specific epitope 1a was inferred to be related to the (α1-2)D-Rha(α1-3) site of the OPS backbone. The serotype-specific epitopes 1b, 1c, 1d, and 1a' were inferred as relating to the immunodominant lateral (α1-3)D-Rha, (β1-4)D-GlcNAc, and (α1-4)D-Fuc substituents and backbone-located site (α1-3)D-Rha(α1-2), respectively, of OPSs that share the common tetra-D-rhamnose repeats in the backbone. A total of 7.3% of the strains studied, all with pathovars morsprunorum and lapsa, were classified as serotypes O2a and O2d within serogroup 02. Serotype-specific epitope 2a was inferred as being related to the backbone-located site D-Rha(α1-3)D-Rha and epitope 2d to the immunodominant lateral (α1-4)D-Fuc residue of OPS consisting of tri-D-rhamnose repeats in the backbone. Epitope 2d alternated with 2a within the same LPS molecule and did not cross-react with epitope 1d. Serotypes O2a and O2d were observed in some strains correlating with the coexpression of the two chemotypes of OPS by the same strain. The serogroup O1-specific MAb Ps1a reacted weakly but definitely with all strains from serogroup 02. We propose serological formulas for serogroups O1 and 02 as well as for individual strains within these serogroups.
Lipopolysaccharide, LPS, characterization, polysaccharide, polysaccharides, Pseudomonas, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, serogroup, backbone, immunochemical, Pseudomonas syringae, classification, D-rhamnose
NCBI PubMed ID: 8932301Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Ltvlov@uta.fi
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Tampere, Finland, Department of Microbiology and Immunology, University of Kiev, Kiev, Ukraine, Institut fur Pflanzenpathologie und Pflanzenschutz der Georg-August-Universitat, Gottingen, Germany
Methods: serological methods
- Article ID: 1073
Ovod V, Knirel Y, Krohn K "Demonstration of the immunochemical diversity of O-chains of lipopolysaccharide of Pseudomonas syringae and inferring of the serogroup- and serotype-specific epitopes with monoclonal antibodies" -
Proceedings of International Conference on Pseudomonas syringae Pathovars and Related Pathogens (5th : 1995 : Berlin, Germany) (1997) Vol. 9, 532-537
Using serogroup- and serotyppe-specific murine monoclonal antibodies (MAbs) to Pseudomonas syringae lipopolysacharide (LPS) O-polysaccharides (OPS) (=O chains) with elucidated primary chemical structure of the O-repeating units, a rather high diversity of the OPS-related epitopes was demonstrated and most of them were inferred. The immunogenic properties of the O-serogroup- and O-serotype-specific epitopes were shown to depend on the nature and the number of sugar residues in the O-repeat as well as on the arrangement of the monosaccharides and the mode of linkages between them.
Lipopolysaccharide, LPS, structure, strain, Pseudomonas, chain, group, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, epitopes, O-polysaccharide, serogroup, immunochemical, O-chain, pathogen, pathogens, pathovar, Pseudomonas syringae, classification, diversity, serotype-specific
Publisher: Kluwer Academic Publishers, The Netherlands
Correspondence: knirel@ioc.ac.ru
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead DE, Vivian A, von Kietzell J
Institutions: Institute of Medical Technology, University of Tampere, Tampere, Finland, N.D. Zelinsy Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 3313
Zdorovenko GM, Zdorovenko EL, Varbanets LD "Composition, structure, and biological properties of lipopolysaccharides from different strains of Pseudomonas syringae pv. atrofaciens" -
Mikrobiologiia = Microbiology [Russian] 76(6) (2007) 683-697
The composition, structure, and certain biological properties of lipopolysaccharides (LPS) isolated from six strains of bacteria Pseudomonas syringae pv.atrofaciens pathogenic for grain-crops (wheat, rye) are presented. The LPS-protein complexes were isolated by a sparing procedure (extraction from microbial cells with a weak salt solution). They reacted with the homologous O sera and contained one to three antigenic determinants. Against the cells of warm-blooded animals (mice, humans) they exhibited the biological activity typical of endotoxins (stimulation of cytokine production, mitogenetic activity, etc.). The LCD of the biovar type strain was highly toxic to mice sensitized with D-galactosamine. The structural components of LPS macromolecules obtained by mild acidic degradation were characterized: lipid A, core oligosaccharide, and O-specific polysaccharide (OPS). Fatty acids 3-HO-C10:0, C12:0, 2-HO-C12:0, 3-HO-C12:0, C16:0, C16:1, C18:0, and C18:1 were identified in lipid A of all the strains, as well as the components of the hydrophilic part: glucosamine (GlcN), ethanolamine (EtN), phosphate, and phosphoethanolamine (EtN-P). In the core LPS, glucose (Glc), rhamnose(Rha), L-glycero-D-manno-heptose (Hep), GlcN, galactosamine (GalN), 2-keto-3-deoxy-D-mannooctonoi acid (KDO), alanine (Ala), and phosphate were present. The O chain of all the strains consisted of repeated elements containing a linear chain of three to four L- (two strains) or D-Rha (four strains) residues supplemented with a single residue of 3-acetamido-3,6-dideoxy-D-galactose (D-Fucp3Nac), N-acetyl-D-glucosamine(D-GlcpNAc), D-fucose (D-Fucf), or D-Rhap (strain-dependent) as a side substituent. In different strains the substitution position for Rha residues in the repeated components of the major rhamnan chain was also different.One strain exhibited a unique type of O-chain heterogeneity. Immunochemical investigation of the LPS antigenic properties revealed the absence of close serological relations between the strains of one pathovar; this finding correlates with the differences in their OPS structure. Resemblance between the investigated strains and other P.syringae strains with similar LPS structures was revealed. The results of LPS analysis indicate the absence of correlation between the OPS structure and the pathovar affiliation of the strains.
Lipopolysaccharide, structure, lipid A, core oligosaccharide, O-specific polysaccharide, biological activity, immunochemistry, Pseudomonas syringae pv.atrofaciens
NCBI PubMed ID: 18297868Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: alz@i.com.ua; evelina@ioc.ac.ru
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
Methods: 13C NMR, 1H NMR, GLC-MS, sugar analysis, serological methods
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