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1. Compound ID: 1646
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b-D-GlcpA-(1-2)-+
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-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: K-antigen, CPS
Contained glycoepitopes: IEDB_115136,IEDB_133754,IEDB_136105,IEDB_140630,IEDB_2116141,IEDB_225177,IEDB_423153,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 510
Zeng Y, Kong F "Synthesis of a hexasaccharide fragment of group E streptococci polysaccharide and the tetrasaccharide repeating unit of E. coli O7:K98:H6" -
Carbohydrate Research 339(8) (2004) 1503-1510
Syntheses of a hexasaccharide, the dimer of the repeating unit of the group E streptococci polysaccharide, and a tetrasaccharide, the repeating unit of the E. coli O7:K98:H6, were achieved by constructing alternate α-L-(1→2)- and α-L-(1→3)-linked l-rhamnopyranose backbones and substituting with β-linked d-glucopyranose side chains for the former, and a d-glucopyranosyluronate branch for the latter, respectively, at O-2 of the l-rhamnose ring.
Rhamnose oligosaccharides, Trichloroacetimidates
NCBI PubMed ID: 15178394Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: fzkong@mail.rcees.ac.cn
Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China
- Article ID: 2201
Hahne M, Jann B, Jann K "Structure of the capsular polysaccharide (K98 antigen) of E. coli O7:K98:H6." -
Carbohydrate Research 222 (1991) 245-253
The capsular polysaccharide (K98 antigen) of E. coli O7:K98:H6 contains rhamnose, glucuronic acid, and acetate in the molar ratios 3:1:0.6. Methylation analysis, oligosaccharide analysis, and 1D- and 2D-n.m.r. spectroscopy revealed the polysaccharide to be a glucuronic acid-substituted rhamnan with the structure [formula; see text] Of the 3-linked rhamnose residues, approximately 60% are O-acetylated at position 2.
NCBI PubMed ID: 1813107Publication DOI: 10.1016/0008-6215(91)89023-9Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Max-Planck-Institut für Immunobiologie, Freiburg-Zähringen, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, ELISA, carboxyl reduction, de-O-acetylation
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2. Compound ID: 1839
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a-D-Fucp3NAc-(1-3)-+
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-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: L-rhamnan
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 578
Ovod V, Zdorovenko EL, Shashkov AS, Kocharova NA, Knirel YA "Structural diversity of the O-polysaccharides and serological classification of Pseudomonas syringae pv. garcae and other strains from genomospecies 4" -
Mikrobiologiia = Microbiology [Russian] 73(6) (2004) 666-677
Novel O-serotypes were revealed among Pseudomonas syringae pv. garcae strains by using a set of mouse monoclonal antibodies specific to the lipopolysaccharide O-polysaccharide. Structural studies showed that the O-polysaccharide of P. syringae pv. garcae NCPPB 2708 is a hitherto unknown linear L-rhamnan lacking strict regularity and having two oligosaccharide repeating units I and II, which differ in the position of substitution in one of the rhamnose residues and have the following structures: I: -3)-a-L-Rha-(1-2)-a-L-Rha-(1-2)-a-L-Rha-(1-3)-a-L-Rha-(1-; II: -3)-a-L-Rha-(1-3)-a-L-Rha-(1-2)-a-L-Rha-(1-3)-a-L-Rha-(1-. The branched O-polysaccharides of P. syringae pv. garcae ICMP 8047 and NCPPB 588T have the same L-rhamnan backbone with repeating units I and II and a lateral chain of (a1-4)- or (a1-3)-linked residues of 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc). Several monoclonal antibody epitopes associated with the L-rhamnan backbone or the lateral a-D-Fuc3NAc residues were characterized
structure, O-polysaccharide, 6-dideoxy-D-galactose, serological classification, 3-Acetamido-3, Pseudomonas syringae, L-rhamnose, diversity
NCBI PubMed ID: 15688937Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: evelina@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technologies, University of Tampere, Tampere, Finland
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, ELISA, GLC, Western blotting
- Article ID: 777
Corsaro MM, De Castro C, Evidente A, Lanzetta R, Lavermicocca P, Molinaro A, Sisto A, Parrilli M, Surico G "Lipopolysaccharides from three phytopathogenic pseudomonads" -
Phytochemistry 46(2) (1997) 289-292
Analysis of the polysaccharide and lipid moieties of the lipopolysaccharides (LPSs) of the phytopathogenic bacteria, Pseudomonas amygdali and P. syringae pv. ciccaronei has demonstrated that for both bacteria, the O-chain consists of a tetrasaccharide repeating unit of three α-L-Rhap and one terminal nonreducing α-D-Fucp3NAc. Two of the rhamnosyl residues are 3-linked, the third one 2,3-linked. This structure had been previously found for the O-chains of three phytopathogenic strains of P. syringae subsp. savastanoi, but this is the first report on its occurrence in P. amygdali and P. syringae pv. ciccaronei. The results of the LPS lipid residue analysis made it possible to make some chemotaxonomic considerations and therefore classify P. amygdali as a chemotype, which is different from that of the other two bacteria examined.
Lipopolysaccharide, lipopolysaccharides, LPS, structure, fatty acids, O-chain, Pseudomonas syringae, Phytopathogenic bacteria, chemotaxonomy, Pseudomonas amygdali
NCBI PubMed ID: 9311153Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Dipartimento di Scienze Chimico-Agrarie, Universita di Napoli Federico II, via Universita 100, I-80055 Portici, Italy, Dipartimento di Chimica Organica e Biologica, Universita di Napoli Federico II, via Mezzocannone 16, I-80134 Napoli, Italy, Instituto Tossine e Micotossine da Parassiti Vegetali del CNR, v.le L Einaudi 51, I-70125, Bari, Italy, Instituto di Patologia e Zoologia Forestale ed Agraria, Uniersita di Firenze, Piazzale delle Cascine 28, I-50144 Firenze, Italy.
Methods: methylation, NMR, sugar analysis, methanolysis
- 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: 1075
Ovod V, Zdorovenko EL, Shashkov AS, Kocharova NA, Knirel YA "Structure of the O polysaccharide and serological classification of Pseudomonas syringae pv. ribicola NCPPB 1010" -
European Journal of Biochemistry 267(8) (2000) 2372-2379
The O polysaccharide (OPS) moiety of the lipopolysaccharide (LPS) of a phytopathogenic bacterium Pseudomonas syringae pv. ribicola NCPPB 1010 was studied by sugar and methylation analyses, Smith degradation, and 1H- and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY and H-detected 1H,13C HMQC experiments. The OPS structure was elucidated, and shown to be composed of branched pentasaccharide repeating units (O repeats) of two types, major (1) and minor (2), differing in the position of substitution of one of the rhamnose residues. Both O repeats form structurally homogeneous blocks within the same polysaccharide molecule. Although P. syringae pv. ribicola NCPPB 1010 demonstrates genetic relatedness and similarity in the OPS chemical structure to some other P. syringae pathovars, it did not cross-react with any OPS-specific mAbs produced against heterologous P. syringae strains. Therefore, we propose to classify P. syringae pv. ribicola NCPPB 1010 in a new serogroup, O8.
structure, structural, polysaccharide, Pseudomonas, O-polysaccharide, O polysaccharide, serological, Pseudomonas syringae, classification, linear, heterogeneity
NCBI PubMed ID: 10759863Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, Finland
Methods: NMR-2D, methylation, NMR, sugar analysis, Smith degradation
- Article ID: 1314
Zdorovenko EL, Zatonsky GV, Zdorovenko GM, Pasichnik LA, Shashkov AS, Knirel YA "Structural heterogeneity in the lipopolysaccharides of Pseudomonas syringae with O-polysaccharide chains having different repeating units" -
Carbohydrate Research 336(4) (2001) 329-336
Studies by sugar and methylation analyses, Smith degradation, and 1H and 13C NMR spectroscopy revealed a structural heterogeneity in the O-polysaccharides of Pseudomonas syringae pvs. coronafaciens IMV 9030 and atrofaciens IMV 8281 owing to the presence of different types of repeating units. In strain IMV 9030, the major repeating units are a linear α-L-rhamnose trisaccharide and a tetrasaccharide (A, n=0 or 1). A minor repeating unit is a branched pentasaccharide with an α-L-rhamnose main chain and a lateral 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc) residue (B, X=2, n=1). In strain IMV 8281, all repeating units are branched and differ in size and position of substitution of one of the α-L-rhamnose residues (tetrasaccharide, B, X=3, n=0; pentasaccharides, B, X=2 or 3, n=1). [structure--see text] Reinvestigation of the structure of the branched O-polysaccharide of P. syringae pv. tomato IPGR 140 showed that, together with the major tetrasaccharide repeating unit (B, X=3, n=0) [Knirel, Y. A., et al. Carbohydr. Res. 1993, 243, 199-204], it has a minor pentasaccharide repeating unit (B, X=3, n=1)
Lipopolysaccharide, O-antigen, Bacterial polysaccharide, Pseudomonas syringae, phytopathogen, structural heterogeneity
NCBI PubMed ID: 11728403Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospeckt 47, Moscow, Russia, Zablotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukra, Zablotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine
Methods: NMR-2D, methylation, NMR, Smith degradation
- Article ID: 1321
Zdorovenko GM, Veremeichenko SN "Comparative characteristics of lipopolysaccharides of various Pseudomonas fluorescens strains (biovar I)" -
Mikrobiologiia = Microbiology [Russian] 70(4) (2001) 441-450
From the biomass of five Pseudomonas fluorescens biovar I strains, including the P. fluorescens type strain IMV 4125 (ATCC13525), lipopolysaccharides (LPS) were isolated (by extraction with a phenol- water mixture followed by repeated ultracentrifugation), as well as individual structural components of the LPS macromolecule: lipid A, the core oligosaccharide, and O-specific polysaccharide (O-PS). 3- Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, dodecanoic, hexadecanoic, octadecanoic, hexadecenoic, and octadecenoic fatty acids were present in lipid A of the LPS of all the strains studied. Glucosamine, ethanolamine, and phosphoethanolamine were revealed in the lipid A hydrophilic part of all of KDO, a trace amount of heptoses, ethanolamine, phosphoethanolamine, alanine, and phosphorus were identified as the main core components. Interstrain differences in the core oligosaccharide composition were revealed. Structural analysis showed that the O-PS of the type strain, as distinct from that of other strains, is heterogeneous and contains two types of repetitive units, including (1) three L-rhamnose residues (L-Rha), one 3-acetamide-3,6-dideoxy-D-galactose residue (D-Fuc3NAc) as a branching substitute of the L-rhamnan chain and (2) three L-Rha residues and two branching D- Fuc3NAc residues. The type strain is also serologically distinct from other biovar I strains due to the LPS O-chain structure, which is similar to those of the strains of the species Pseudomonas syringae, including the type strain. The data of structural analysis agree well with the results of immunochemical studies of LPS.
Lipopolysaccharide, structure, lipid A, core oligosaccharide, O-specific polysaccharide, Pseudomonas fluorescens, serological cross reactivity
NCBI PubMed ID: 11558277Publication DOI: 10.1023/A:1010486211742Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: zdorov@i.kiev.ua
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kiev, 252143 Ukraine
- 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: 2252
Knirel YA, Shashkov AS, Paramonov NA, Zdorovenko GM, Solyanic LP, Yakovleva LM "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide of Pseudomonas syringae pv. tomato 140(R)" -
Carbohydrate Research 243 (1993) 199-204
No abstract available
NCBI PubMed ID: 8324762Publication DOI: 10.1016/0008-6215(93)84092-kJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
Methods: 13C NMR, 1H NMR, NMR-2D, GLC
- Article ID: 3298
Adinolfi M, Corsaro MM, Lanzetta R, Marciano CE, Parrilli M, Evidente A, Surico G "Structure of the O-chain polysaccharide of three strains of Pseudomonas syringae ssp. savastanoi" -
Canadian Journal of Chemistry 72 (1994) 1839-1843
The structure of the O-chain portion of the lipopolysaccharide isolated from three different strains of Pseudomonas syringae ssp. savastanoi has been determined by chemical and NMR spectral analysis. For all of the strains the O-chain consists of a tetrasaccharide repeating unit of three ?-L-Rhap and one terminal nonreducing ?-D-Fucp3NAc. Two rhamnosyl residues are 3-linked and the third one is 2,3-linked. LPS from an olive strain, avirulent on oleander, was shown to attenuate the response of oleander plants inoculated with a homologous strain.
Lipopolysaccharide, NMR, LPS, structure, tetrasaccharide, strain, terminal, polysaccharide, repeating unit, analysis, Pseudomonas, chemical, O-chain, Pseudomonas syringae, nonreducing, plant
Publication DOI: 10.1139/v94-233Journal NLM ID: 0372705WWW link: http://www.nrcresearchpress.com/doi/pdf/10.1139/v94-233Publisher: National Research Council of Canada Canada
Institutions: Dipartirnento di Chirnica Organica e Biologics, Universita di Napoli Federico 11, Wa Mezzocannone 16,80134 Napoli, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, GLC, NMR-1D
- 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: 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: 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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3. Compound ID: 2475
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a-D-Fucp3NAc-(1-2)-+
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-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: L-rhamnan
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 848
Knirel YA, Zdorovenko GM, Paramonov NA, Veremeychenko SN, Toukach FV, Shashkov AS "Somatic antigens of pseudomonads: Structure of the O-specific polysaccharide of the reference strain for Pseudomonas fluorescens (IMV 4125, ATCC13525, biovar A)" -
Carbohydrate Research 291 (1996) 217-224
Lipopolysaccharide, antigen, LPS, structure, Bacterial, strain, polysaccharide, O-antigen, Pseudomonas, antigens, NMR spectroscopy, O-specific, O-specific polysaccharide, 6-dideoxy-D-galactose, reference, 3-Acetamido-3, biovar, Pseudomonas fluorescens, somatic
NCBI PubMed ID: 8864233Journal 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, Smith degradation
- Article ID: 856
Knirel YA, Ovod VV, Paramonov NA, Krohn KJ "Structural heterogeneity in the O polysaccharide of Pseudomonas syringae pv. coriandricola GSPB 2028 (NCPPB 3780, W-43)" -
European Journal of Biochemistry 258 (1998) 716-721
The O polysaccharide (OPS) of the lipopolysaccharide of Pseudomonas syringae pv. coriandricola GSPB 2028 (NCPPB 3780, W-43) was studied by Smith degradation and 1H NMR and 13C NMR spectroscopy, including two-dimensional COSY, TOCSY, NOESY, and H-detected 1H,13C heteronuclear multiple-quantum coherence (HMQC) experiments. The OPS was shown to consist of pentasaccharide O repeats of two types both containing four L-rhamnose and one 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc) residue. Structure 1 of the major O repeat which had been established earlier [Das, S., Ramm, M., Kochanowski, H. & Basu, S. (1994) J. Bacteriol. 176, 6550-6557], was confirmed by our data, and a new structure 2 was elucidated for the minor O repeat and found to differ from the structure 1 only in the position of substitution of one of the rhamnose residues in the main chain. [structures: see text] A role of structural and immunochemical features of the LPS for defining the taxonomical position of the bacterium studied is discussed.
Lipopolysaccharide, LPS, structure, strain, structural, characterization, polysaccharide, Pseudomonas, antibody, monoclonal, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, 6-dideoxy-D-galactose, serogroup, backbone, immunochemical, 3-Acetamido-3, Pseudomonas syringae, L-rhamnose, classification, heterogeneity
NCBI PubMed ID: 9874239Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, Smith degradation
- Article ID: 1318
Zdorovenko GM, Solyanic LP, Yakovleva LM, Paramonov NA "Characterization of O-antigens from different strains of Pseudomonas syringae pv. tabaci" -
Biochemistry (Moscow) 62(1) (1997) 28-37
O-Antigens (lipopolysaccharides, LPS) were isolated by NaCl extraction from microbial biomass of Pseudomonas syringae pv. tabaci and purified by ultracentrifugation. Individual structural components of the LPS macromolecule (O-specific polysaccharide (O-PS), core oligosaccharide, and lipid A) were obtained and characterized. Fatty acids 3-OH-C10:0, C12:0, 2-OH-C12:0, 3-OH-C12:0, C16:1, C16:0, C18:1, and C18:0 were identified in the lipid A composition. Glucosamine, ethanolamine, and phosphoethanolamine were found in the hydrophilic part of the lipid A macromolecule in all strains tested. Lipid A preparations contained phosphorus and amino acids. Rhamnose, glucose, glucosamine, 2-keto-3-deoxyoctulosonic acid, heptose, alanine, and phosphorus were identified as the main core components. The strains differed in O-PS structure. We describe the O-chain of LPS in strain P-28. It contains repeating units of the following structure: [formula: see text] The O-PS structures of LPS from strains P-28 and 225 are identical, however, they differ substantially from that of strain 223. Both structures from strains 223 and 225 were reported previously. Antibodies to antigenic epitopes of O-PS, core, and lipid A were revealed in O-serum against the whole bacterial cells. Correlation of O-PS structure with the serological grouping of strains was observed
Lipopolysaccharide, core, O-antigen, lipid A, Pseudomonas syringae, O-antigenlipopolysaccharide, O-specific polyaccharide, composition and structure of lipoplysaccharide
NCBI PubMed ID: 9113726Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: zdorov@i.kiev.ua
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine
Methods: NMR-2D, methylation, NMR
- Article ID: 1321
Zdorovenko GM, Veremeichenko SN "Comparative characteristics of lipopolysaccharides of various Pseudomonas fluorescens strains (biovar I)" -
Mikrobiologiia = Microbiology [Russian] 70(4) (2001) 441-450
From the biomass of five Pseudomonas fluorescens biovar I strains, including the P. fluorescens type strain IMV 4125 (ATCC13525), lipopolysaccharides (LPS) were isolated (by extraction with a phenol- water mixture followed by repeated ultracentrifugation), as well as individual structural components of the LPS macromolecule: lipid A, the core oligosaccharide, and O-specific polysaccharide (O-PS). 3- Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, dodecanoic, hexadecanoic, octadecanoic, hexadecenoic, and octadecenoic fatty acids were present in lipid A of the LPS of all the strains studied. Glucosamine, ethanolamine, and phosphoethanolamine were revealed in the lipid A hydrophilic part of all of KDO, a trace amount of heptoses, ethanolamine, phosphoethanolamine, alanine, and phosphorus were identified as the main core components. Interstrain differences in the core oligosaccharide composition were revealed. Structural analysis showed that the O-PS of the type strain, as distinct from that of other strains, is heterogeneous and contains two types of repetitive units, including (1) three L-rhamnose residues (L-Rha), one 3-acetamide-3,6-dideoxy-D-galactose residue (D-Fuc3NAc) as a branching substitute of the L-rhamnan chain and (2) three L-Rha residues and two branching D- Fuc3NAc residues. The type strain is also serologically distinct from other biovar I strains due to the LPS O-chain structure, which is similar to those of the strains of the species Pseudomonas syringae, including the type strain. The data of structural analysis agree well with the results of immunochemical studies of LPS.
Lipopolysaccharide, structure, lipid A, core oligosaccharide, O-specific polysaccharide, Pseudomonas fluorescens, serological cross reactivity
NCBI PubMed ID: 11558277Publication DOI: 10.1023/A:1010486211742Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: zdorov@i.kiev.ua
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kiev, 252143 Ukraine
- 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: 1877
Shashkov AS, Zdorovenko GM, Daeva ED, Yakovleva LM, Solyanik LP, Gvozdyak RI, Knirel YA, Kochetkov NK "Antigenic polysaccharides of bacteria. 37. Structure of the polysaccharide chain of Pseudomonas syringae pv. tabaci (serogroup VII) lipopolysaccharide" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 16(1) (1990) 90-97
The structure of the O-specific polysaccharide chain of Pseudomonas syringae pv. tabaci strain 223 (serogroup VII) lipopolysaccharide was established on the basis of one- and two-dimensional 1H NMR analysis, 13C NMR analysis and calculation of optical rotation. The structure determined by the non-destructive way was confirmed by acid hydrolysis and methylation. (Sequence: see text). O-Antigen of the strain studied is similar in structure and serological properties to O-antigens of Pseudomonas syringae strains belonging to serogroup I.
NCBI PubMed ID: 1693273Journal 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, NMR-2D
- 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: 2252
Knirel YA, Shashkov AS, Paramonov NA, Zdorovenko GM, Solyanic LP, Yakovleva LM "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide of Pseudomonas syringae pv. tomato 140(R)" -
Carbohydrate Research 243 (1993) 199-204
No abstract available
NCBI PubMed ID: 8324762Publication DOI: 10.1016/0008-6215(93)84092-kJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
Methods: 13C NMR, 1H NMR, NMR-2D, GLC
- Article ID: 3338
Spitali M, Smith ARW "Structure of the Lipopolysaccharide Side Chain of Pseudomonas syringae pv. tabaci Strain NCPPB 79 (?CFBP 1615), in Relation to O-serogroup" -
Phytopathologische Zeitschrift = Journal of Phytopathology 155(1) (2007) 1-7
The lipopolysaccharide (LPS) side chain from Pseudomonas syringae pv. tabaci strain NCPPB 79 (=CFBP 1615) contained l- and d-rhamnose, and GlcNAc. Using methylation analysis, periodate oxidation, Smith degradation and 1H- and 13C-nuclear magnetic resonance spectroscopy, the repeat unit was found to have the structure: 3)[bGlcNac(1-4)]-a-D-Rhap(1-3)-b-L-Rhap(1-4)-a-L-Rhap(1- . This structure is correlated with a previously proposed serogrouping system. The involvement of LPS generally in plant disease is briefly discussed.
Lipopolysaccharide, structure, strain, side chain, Pseudomonas syringae, Serogrouping, Pseudomonas syringae pv. tabaci
Publication DOI: 10.1111/j.1439-0434.2006.01159.xJournal NLM ID: 9875585Publisher: Berlin: Parey
Correspondence: SmaA672@aol.com
Institutions: Department of Life Sciences, University of Greenwich at Medway, Central Avenue, Chatham Maritime, Kent ME4 4TB, UK
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, acid hydrolysis, GC, Smith degradation, NMR-1D, serological methods, periodate oxidation
- 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: 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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4. Compound ID: 2476
|
a-D-Fucp3NAc-(1-2)-+
|
a-D-Fucp3NAc-(1-2)-+ |
| |
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 848
Knirel YA, Zdorovenko GM, Paramonov NA, Veremeychenko SN, Toukach FV, Shashkov AS "Somatic antigens of pseudomonads: Structure of the O-specific polysaccharide of the reference strain for Pseudomonas fluorescens (IMV 4125, ATCC13525, biovar A)" -
Carbohydrate Research 291 (1996) 217-224
Lipopolysaccharide, antigen, LPS, structure, Bacterial, strain, polysaccharide, O-antigen, Pseudomonas, antigens, NMR spectroscopy, O-specific, O-specific polysaccharide, 6-dideoxy-D-galactose, reference, 3-Acetamido-3, biovar, Pseudomonas fluorescens, somatic
NCBI PubMed ID: 8864233Journal 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, Smith degradation
- Article ID: 856
Knirel YA, Ovod VV, Paramonov NA, Krohn KJ "Structural heterogeneity in the O polysaccharide of Pseudomonas syringae pv. coriandricola GSPB 2028 (NCPPB 3780, W-43)" -
European Journal of Biochemistry 258 (1998) 716-721
The O polysaccharide (OPS) of the lipopolysaccharide of Pseudomonas syringae pv. coriandricola GSPB 2028 (NCPPB 3780, W-43) was studied by Smith degradation and 1H NMR and 13C NMR spectroscopy, including two-dimensional COSY, TOCSY, NOESY, and H-detected 1H,13C heteronuclear multiple-quantum coherence (HMQC) experiments. The OPS was shown to consist of pentasaccharide O repeats of two types both containing four L-rhamnose and one 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc) residue. Structure 1 of the major O repeat which had been established earlier [Das, S., Ramm, M., Kochanowski, H. & Basu, S. (1994) J. Bacteriol. 176, 6550-6557], was confirmed by our data, and a new structure 2 was elucidated for the minor O repeat and found to differ from the structure 1 only in the position of substitution of one of the rhamnose residues in the main chain. [structures: see text] A role of structural and immunochemical features of the LPS for defining the taxonomical position of the bacterium studied is discussed.
Lipopolysaccharide, LPS, structure, strain, structural, characterization, polysaccharide, Pseudomonas, antibody, monoclonal, monoclonal antibody, O-polysaccharide, O polysaccharide, bacteria, 6-dideoxy-D-galactose, serogroup, backbone, immunochemical, 3-Acetamido-3, Pseudomonas syringae, L-rhamnose, classification, heterogeneity
NCBI PubMed ID: 9874239Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, Smith degradation
- Article ID: 1321
Zdorovenko GM, Veremeichenko SN "Comparative characteristics of lipopolysaccharides of various Pseudomonas fluorescens strains (biovar I)" -
Mikrobiologiia = Microbiology [Russian] 70(4) (2001) 441-450
From the biomass of five Pseudomonas fluorescens biovar I strains, including the P. fluorescens type strain IMV 4125 (ATCC13525), lipopolysaccharides (LPS) were isolated (by extraction with a phenol- water mixture followed by repeated ultracentrifugation), as well as individual structural components of the LPS macromolecule: lipid A, the core oligosaccharide, and O-specific polysaccharide (O-PS). 3- Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, dodecanoic, hexadecanoic, octadecanoic, hexadecenoic, and octadecenoic fatty acids were present in lipid A of the LPS of all the strains studied. Glucosamine, ethanolamine, and phosphoethanolamine were revealed in the lipid A hydrophilic part of all of KDO, a trace amount of heptoses, ethanolamine, phosphoethanolamine, alanine, and phosphorus were identified as the main core components. Interstrain differences in the core oligosaccharide composition were revealed. Structural analysis showed that the O-PS of the type strain, as distinct from that of other strains, is heterogeneous and contains two types of repetitive units, including (1) three L-rhamnose residues (L-Rha), one 3-acetamide-3,6-dideoxy-D-galactose residue (D-Fuc3NAc) as a branching substitute of the L-rhamnan chain and (2) three L-Rha residues and two branching D- Fuc3NAc residues. The type strain is also serologically distinct from other biovar I strains due to the LPS O-chain structure, which is similar to those of the strains of the species Pseudomonas syringae, including the type strain. The data of structural analysis agree well with the results of immunochemical studies of LPS.
Lipopolysaccharide, structure, lipid A, core oligosaccharide, O-specific polysaccharide, Pseudomonas fluorescens, serological cross reactivity
NCBI PubMed ID: 11558277Publication DOI: 10.1023/A:1010486211742Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: zdorov@i.kiev.ua
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kiev, 252143 Ukraine
- 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
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5. Compound ID: 3000
|
a-D-Fucp3NAc-(1-2)-+
|
-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- 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: 2190
Vinogradov EV, Shashkov AS, Knirel YA, Zdorovenko GM, Solyanik LP, Gubanova NY, Yakovleva LM "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide chain of Pseudomonas syringae pv. tabaci 225 (serogroup VIII) lipopolysaccharide" -
Carbohydrate Research 212 (1991) 307-311
No abstract available
NCBI PubMed ID: 1720348Publication DOI: 10.1016/0008-6215(91)84071-lJournal 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, GLC, de-N-acetylation/deamination
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6. Compound ID: 3264
|
65%b-L-Xylp-(1-4)-+
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b-L-Xylp-(1-2)-+ |
| |
-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1195
Senchenkova SN, Shashkov AS, Laux P, Knirel YA, Rudolph K "The O-chain polysaccharide of the lipopolysaccharide of Xanthomonas campestris pv. begoniae GSPB 525 is a partially L-xylosylated L-rhamnan" -
Carbohydrate Research 319(1-4) (1999) 148-153
Lipopolysaccharide, LPS, structure, strain, structural, characterization, polysaccharide, ion, O-polysaccharide, O polysaccharide, bacteria, O-chain, L-rhamnose, Xanthomonas, Xanthomonas campestris, heterogeneity, L-xylose
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: 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
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7. Compound ID: 3456
Structure type: polymer chemical repeating unit
Trivial name: O-antigen A-band
Compound class: O-polysaccharide, K-antigen, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1314
Zdorovenko EL, Zatonsky GV, Zdorovenko GM, Pasichnik LA, Shashkov AS, Knirel YA "Structural heterogeneity in the lipopolysaccharides of Pseudomonas syringae with O-polysaccharide chains having different repeating units" -
Carbohydrate Research 336(4) (2001) 329-336
Studies by sugar and methylation analyses, Smith degradation, and 1H and 13C NMR spectroscopy revealed a structural heterogeneity in the O-polysaccharides of Pseudomonas syringae pvs. coronafaciens IMV 9030 and atrofaciens IMV 8281 owing to the presence of different types of repeating units. In strain IMV 9030, the major repeating units are a linear α-L-rhamnose trisaccharide and a tetrasaccharide (A, n=0 or 1). A minor repeating unit is a branched pentasaccharide with an α-L-rhamnose main chain and a lateral 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc) residue (B, X=2, n=1). In strain IMV 8281, all repeating units are branched and differ in size and position of substitution of one of the α-L-rhamnose residues (tetrasaccharide, B, X=3, n=0; pentasaccharides, B, X=2 or 3, n=1). [structure--see text] Reinvestigation of the structure of the branched O-polysaccharide of P. syringae pv. tomato IPGR 140 showed that, together with the major tetrasaccharide repeating unit (B, X=3, n=0) [Knirel, Y. A., et al. Carbohydr. Res. 1993, 243, 199-204], it has a minor pentasaccharide repeating unit (B, X=3, n=1)
Lipopolysaccharide, O-antigen, Bacterial polysaccharide, Pseudomonas syringae, phytopathogen, structural heterogeneity
NCBI PubMed ID: 11728403Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospeckt 47, Moscow, Russia, Zablotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukra, Zablotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine
Methods: NMR-2D, methylation, NMR, Smith degradation
- Article ID: 1339
Zubkov VA, Nazarenko EL, Ivanova EP, Gorshkova NM, Gorshkova RP "Structure of the repeating unit of the O-specific polysaccharide of Marinomonas communis strain ATCC27118(T)" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 25(4) (1999) 290-292
O-specific polysaccharide was isolated from the bacteria Marinomonas communis strain ATCC27118(T) and studied by NMR spectroscopy and chemical methods. As a result following structure of the repeating unit was determined [see text]
structure, strain, polysaccharide, repeating unit, O-specific, O-specific polysaccharide, Marinomonas
Journal NLM ID: 7804941Publisher: Moskva: Nauka
Correspondence: elnaz@piboc.marine.su
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok
Methods: NMR-2D, methylation, NMR
- Article ID: 1642
Reuhs BL, Relic B, Forsberg LS, Marie C, Ojanen-Reuhs T, Stephens SB, Wong CH, Jabbouri S, Broughtjn WL "Structural characterization of a flavonoid-inducible Pseudomonas aeruginosa A-band-like O antigen of Rhizobium sp. strain NGR234, required for the formation of nitrogen-fixing nodules" -
Journal of Bacteriology 187(18) (2005) 6479-6487
Rhizobium (Sinorhizobium) sp. strain NGR234 contains three replicons, the smallest of which (pNGR234a) carries most symbiotic genes, including those required for nodulation and lipo-chito-oligosaccharide (Nod factor) biosynthesis. Activation of nod gene expression depends on plant-derived flavonoids, NodD transcriptional activators, and nod box promoter elements. Nod boxes NB6 and NB7 delimit six different types of genes, one of which (fixF) is essential for the formation of effective nodules on Vigna unguiculata. In vegetative culture, wild-type NGR234 produces a distinct, flavonoid-inducible lipopolysaccharide (LPS) that is not produced by the mutant (NGRomegafixF); this LPS is also found in nitrogen-fixing bacteroids isolated from V. unguiculata infected with NGR234. Electron microscopy showed that peribacteroid membrane formation is perturbed in nodule cells infected by the fixF mutant. LPSs were purified from free-living NGR234 cultured in the presence of apigenin. Structural analyses showed that the polysaccharide portions of these LPSs are specialized, rhamnose-containing O antigens attached to a modified core-lipid A carrier. The primary sequence of the O antigen is [-3)-α-L-Rhap-(1,3)-α-L-Rhap-(1,2)-α-L-Rhap-(1-]n, and the LPS core region lacks the acidic sugars commonly associated with the antigenic outer core of LPS from noninduced cells. This rhamnan O antigen, which is absent from noninduced cells, has the same primary sequence as the A-band O antigen of Pseudomonas aeruginosa, except that it is composed of L-rhamnose rather than the D-rhamnose characteristic of the latter. It is noteworthy that A-band LPS is selectively maintained on the P. aeruginosa cell surface during chronic cystic fibrosis lung infection, where it is associated with an increased duration of infection.
antigen, strain, structural, characterization, O-antigen, O antigen, Pseudomonas, Pseudomonas aeruginosa, Rhizobia, Rhizobium, formation, nitrogen fixing, nodule
NCBI PubMed ID: 16159781Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: william.broughton@bioveg.unige.ch
Institutions: Whistler Center for Carbohydrate Research, Department of Food Science, Purdue University, 1160 Food Science Building, West Lafayette, Indiana 47907-11601, LBMPS, Universite de Geneve, 30 quai Ernest-Ansermet, 1211 Geneve 4, Switzerland, Complex Carbohydrate Research Center, The University of Georgia, 315 Riverbend Rd., Athens, GA, USA3, Pusat Penyelidikan Sains Kajihayat, Universiti Sains Malaysia, Pulau Pinang, Malaysia
Methods: NMR
- Article ID: 2108
Dengler T, Himmelspach K, Jann B, Jann K "Structure of the capsular K3 antigen of Escherichia coli O4:K3:H4, a polysaccharide containing a 4-deoxy-2-hexulosonic acid" -
Carbohydrate Research 178 (1988) 191-201
Journal NLM ID: 0043535Publisher: Elsevier
- 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: 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: 4441
Bedini E, Carabellese A, Comegna D, De Castro C, Parrilli M "Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria" -
Tetrahedron 62(36) (2006) 8474-8483
The synthesis of the tetrasaccharide rhamnanic motif a-l-Rha-(1-3)-a-l-Rha-(1-2)-a-l-Rha-(1-2)-a-l-Rha and its dimerization to octasaccharide have been developed. Three different pathways toward the dimerization have been investigated; the best one was based on a [4+2]+2 stepwise condensation of a rhamnose tetrasaccharide with two rhamnosyl N-phenyl trifluoroacetimidates as glycosyl donors and on an orthogonal set of protecting groups consisting of benzoyl, levulinoyl, and allyl groups.
Lipopolysaccharide, oligosaccharide, rhamnose, glycosylation, Phytopathogenic bacteria
Publication DOI: 10.1016/j.tet.2006.06.084Journal NLM ID: 2984170RPublisher: Pergamon Press
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
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, chemical methods
- Article ID: 5177
Laguri C, Silipo A, Martorana AM, Schanda P, Marchetti R, Polissi A, Molinaro A, Simorre JP "Solid State NMR Studies of Intact Lipopolysaccharide Endotoxin" -
ACS Chemical Biology 13(8) (2018) 2106-2113
Lipopolysaccharides (LPS) are complex glycolipids forming the outside layer of Gram-negative bacteria. Their hydrophobic and heterogeneous nature greatly hampers their structural study in an environment similar to the bacterial surface. We have studied LPS purified from E. coli and pathogenic P. aeruginosa with long O-antigen polysaccharides assembled in solution as vesicles or elongated micelles. Solid-state NMR with magic-angle spinning permitted the identification of NMR signals arising from regions with different flexibilities in the LPS, from the lipid components to the O-antigen polysaccharides. Atomic scale data on the LPS enabled the study of the interaction of gentamicin antibiotic bound to P. aeruginosa LPS, for which we could confirm that a specific oligosaccharide is involved in the antibiotic binding. The possibility to study LPS alone and bound to a ligand when it is assembled in membrane-like structures opens great prospects for the investigation of proteins and antibiotics that specifically target such an important molecule at the surface of Gram-negative bacteria.
NMR, LPS, O-antigen, identification, solid state, endotoxin, structural studies, glycolipid
NCBI PubMed ID: 29965728Publication DOI: 10.1021/acschembio.8b00271Journal NLM ID: 101282906Publisher: Washington, DC: American Chemical Society
Correspondence: molinaro@unina.it; jean-pierre.simorre@ibs.fr
Institutions: Universite Grenoble Alpes, CNRS, CEA, IBS, F-38000 Grenoble, France, University of Naples Federico II, Department of Chemical Sciences, via cintia 4, Napoli, Italy, University of Milano, Department of Pharmacological and Biomolecular Sciences, Via Balzaretti 9, Milano, Italy
Methods: STD NMR, MAS STD NMR
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8. Compound ID: 3462
|
Fucp3NAc-(1-2)-+
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1321
Zdorovenko GM, Veremeichenko SN "Comparative characteristics of lipopolysaccharides of various Pseudomonas fluorescens strains (biovar I)" -
Mikrobiologiia = Microbiology [Russian] 70(4) (2001) 441-450
From the biomass of five Pseudomonas fluorescens biovar I strains, including the P. fluorescens type strain IMV 4125 (ATCC13525), lipopolysaccharides (LPS) were isolated (by extraction with a phenol- water mixture followed by repeated ultracentrifugation), as well as individual structural components of the LPS macromolecule: lipid A, the core oligosaccharide, and O-specific polysaccharide (O-PS). 3- Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, dodecanoic, hexadecanoic, octadecanoic, hexadecenoic, and octadecenoic fatty acids were present in lipid A of the LPS of all the strains studied. Glucosamine, ethanolamine, and phosphoethanolamine were revealed in the lipid A hydrophilic part of all of KDO, a trace amount of heptoses, ethanolamine, phosphoethanolamine, alanine, and phosphorus were identified as the main core components. Interstrain differences in the core oligosaccharide composition were revealed. Structural analysis showed that the O-PS of the type strain, as distinct from that of other strains, is heterogeneous and contains two types of repetitive units, including (1) three L-rhamnose residues (L-Rha), one 3-acetamide-3,6-dideoxy-D-galactose residue (D-Fuc3NAc) as a branching substitute of the L-rhamnan chain and (2) three L-Rha residues and two branching D- Fuc3NAc residues. The type strain is also serologically distinct from other biovar I strains due to the LPS O-chain structure, which is similar to those of the strains of the species Pseudomonas syringae, including the type strain. The data of structural analysis agree well with the results of immunochemical studies of LPS.
Lipopolysaccharide, structure, lipid A, core oligosaccharide, O-specific polysaccharide, Pseudomonas fluorescens, serological cross reactivity
NCBI PubMed ID: 11558277Publication DOI: 10.1023/A:1010486211742Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: zdorov@i.kiev.ua
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kiev, 252143 Ukraine
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9. Compound ID: 4053
|
a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rha-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rha-(1-7)-Bn |
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Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1495
Bedini E, De Castro C, Erbs G, Mangoni L, Dow JM, Newman MA, Parrilli M, Unverzagt C "Structure-dependent modulation of a pathogen response in plants by synthetic O-antigen polysaccharides" -
Journal of the American Chemical Society 127(8) (2005) 2414-2416
Many phytopathogenic bacteria display lipopolysaccharides (LPS) with the O-chain repeating unit [α-L-Rha-(1→3)-α-L-Rha-(1→3)-α-L-Rha-(1→2)](n). This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressing the hypersensitive response (HR) and in inducing PR-1 gene expression in Arabidopsis thaliana. Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculations revealed that a coiled structure develops with increasing chain length of the oligosaccharide. This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP)
Lipopolysaccharide, structure, O-antigen, molecular dynamics, NMR spectroscopy, conformational analysis, Pseudomonas syringae, gene expression, rhamnan, Arabidopsis
NCBI PubMed ID: 15724995Journal NLM ID: 7503056Publisher: American Chemical Society
Institutions: Dipartimento di Chimica Organica e Biochimica Complesso, Universitario Monte Sant'Angelo, Via Cintia 4, 80126, Napoli, Italy, Section for Plant Pathology, Royal Veterinary and Agricultural University, Thorvaldsensvej 40, 1871 Frederiksberg, Denmark, BIOMERIT Research Centre, Department of Microbiology, BioSciences Institute, National University of Ireland, Cork, Ireland, Bioorganische Chemie, Gebäude NWI, Universität Bayreuth, D-95440 Bayreuth, Germany
Methods: NMR-2D, NMR, chemical synthesis, biological assays, MD simulations
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10. Compound ID: 4368
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_137477,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1642
Reuhs BL, Relic B, Forsberg LS, Marie C, Ojanen-Reuhs T, Stephens SB, Wong CH, Jabbouri S, Broughtjn WL "Structural characterization of a flavonoid-inducible Pseudomonas aeruginosa A-band-like O antigen of Rhizobium sp. strain NGR234, required for the formation of nitrogen-fixing nodules" -
Journal of Bacteriology 187(18) (2005) 6479-6487
Rhizobium (Sinorhizobium) sp. strain NGR234 contains three replicons, the smallest of which (pNGR234a) carries most symbiotic genes, including those required for nodulation and lipo-chito-oligosaccharide (Nod factor) biosynthesis. Activation of nod gene expression depends on plant-derived flavonoids, NodD transcriptional activators, and nod box promoter elements. Nod boxes NB6 and NB7 delimit six different types of genes, one of which (fixF) is essential for the formation of effective nodules on Vigna unguiculata. In vegetative culture, wild-type NGR234 produces a distinct, flavonoid-inducible lipopolysaccharide (LPS) that is not produced by the mutant (NGRomegafixF); this LPS is also found in nitrogen-fixing bacteroids isolated from V. unguiculata infected with NGR234. Electron microscopy showed that peribacteroid membrane formation is perturbed in nodule cells infected by the fixF mutant. LPSs were purified from free-living NGR234 cultured in the presence of apigenin. Structural analyses showed that the polysaccharide portions of these LPSs are specialized, rhamnose-containing O antigens attached to a modified core-lipid A carrier. The primary sequence of the O antigen is [-3)-α-L-Rhap-(1,3)-α-L-Rhap-(1,2)-α-L-Rhap-(1-]n, and the LPS core region lacks the acidic sugars commonly associated with the antigenic outer core of LPS from noninduced cells. This rhamnan O antigen, which is absent from noninduced cells, has the same primary sequence as the A-band O antigen of Pseudomonas aeruginosa, except that it is composed of L-rhamnose rather than the D-rhamnose characteristic of the latter. It is noteworthy that A-band LPS is selectively maintained on the P. aeruginosa cell surface during chronic cystic fibrosis lung infection, where it is associated with an increased duration of infection.
antigen, strain, structural, characterization, O-antigen, O antigen, Pseudomonas, Pseudomonas aeruginosa, Rhizobia, Rhizobium, formation, nitrogen fixing, nodule
NCBI PubMed ID: 16159781Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: william.broughton@bioveg.unige.ch
Institutions: Whistler Center for Carbohydrate Research, Department of Food Science, Purdue University, 1160 Food Science Building, West Lafayette, Indiana 47907-11601, LBMPS, Universite de Geneve, 30 quai Ernest-Ansermet, 1211 Geneve 4, Switzerland, Complex Carbohydrate Research Center, The University of Georgia, 315 Riverbend Rd., Athens, GA, USA3, Pusat Penyelidikan Sains Kajihayat, Universiti Sains Malaysia, Pulau Pinang, Malaysia
Methods: NMR
- Article ID: 3829
Carlson RW, Forsberg LS, Kannenberg EL "Lipopolysaccharides in Rhizobium-Legume Symbioses" -
Book: Endotoxins: Structure, Function and Recognition (series: Subcellular Biochemistry, 2010, Part 1) (2010) Vol. 53, Chapter 16, 339-386
The establishment of nitrogen-fixing symbiosis between a legume plant and its rhizobial symbiont requires that the bacterium adapt to changing conditions that occur with the host plant that both promotes and allows infection of the host root nodule cell, regulates and resists the host defense response, permits the exchange of metabolites, and contributes to the overall health of the host. This adaptive process involves changes to the bacterial cell surface and, therefore, structural modifications to the lipopolysaccharide (LPS). In this chapter, we describe the structures of the LPSs from symbiont members of the Rhizobiales, the genetics and mechanism of their biosynthesis, the modifications that occur during symbiosis, and their possible functions.
biosynthesis, lipopolysaccharides, structure, Rhizobium, symbiosis, plant defense
NCBI PubMed ID: 20593275Publication DOI: 10.1007/978-90-481-9078-2_16Publisher: Springer Science+Business Media B.V.
Correspondence: rcarlson@ccrc.uga.edu
Editors: Wang X, Quinn PJ
Institutions: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Rd., Athens, GA 30602, USA
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11. Compound ID: 4645
|
a-D-Fucp3NAc-(1-4)-+
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- 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: 5322
|
b-D-GlcpA-(1-2)-+
|
-3)-a-L-Rhap2(60%)Ac-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: K-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130422,IEDB_133754,IEDB_136105,IEDB_140630,IEDB_2116141,IEDB_225177,IEDB_423153,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 2201
Hahne M, Jann B, Jann K "Structure of the capsular polysaccharide (K98 antigen) of E. coli O7:K98:H6." -
Carbohydrate Research 222 (1991) 245-253
The capsular polysaccharide (K98 antigen) of E. coli O7:K98:H6 contains rhamnose, glucuronic acid, and acetate in the molar ratios 3:1:0.6. Methylation analysis, oligosaccharide analysis, and 1D- and 2D-n.m.r. spectroscopy revealed the polysaccharide to be a glucuronic acid-substituted rhamnan with the structure [formula; see text] Of the 3-linked rhamnose residues, approximately 60% are O-acetylated at position 2.
NCBI PubMed ID: 1813107Publication DOI: 10.1016/0008-6215(91)89023-9Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Max-Planck-Institut für Immunobiologie, Freiburg-Zähringen, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, ELISA, carboxyl reduction, de-O-acetylation
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13. Compound ID: 7777
|
b-D-Glcp-(1-3)-+
|
-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_2116141,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3464
Fedonenko YP, Zdorovenko EL, Konnova SA, Kachala VV, Ignatov VV "Structural analysis of the O-antigen of the lipopolysaccharide from Azospirillum lipoferum SR65" -
Carbohydrate Research 343(16) (2008) 2841-2844
A neutral O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide isolated by phenol/water extraction from the asymbiotic diazotrophic rhizobacterium Azospirillum lipoferum SR65. The following structure of the O-polysaccharide was established by composition and methylation analyses, Smith degradation, and 1H and 13C NMR spectroscopy, including a 2D ROESY experiment:
Lipopolysaccharide, bacterial polysaccharide structure, Azospirillum lipoferum
NCBI PubMed ID: 18561903Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E.L. Zdorovenko
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Prospekt Entuziastov 13, 410049 Saratov, Russia.
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, chemical analysis, Smith degradation
- 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: 4015
Fedonenko YP, Boyko AS, Zdorovenko EL, Konnova SA, Shashkov AS, Ignatov VV, Knirel YA "Structural pecularities of the O-specific polysaccharides of Azospirillum bacteria of serogroup III" -
Biochemistry (Moscow) 76(7) (2011) 797-802
Azospirillum brasilense SR55, isolated from the rhizosphere of Triticum durum, was classified as serogroup II on the basis of serological tests. Such serogroup affiliation is uncharacteristic of wheat-associated Azospirillum species. The lipid A of A. brasilense SR55 lipopolysaccharide contained 3-hydroxytetradecanoic, 3-hydroxyhexadecanoic, hexadecanoic and octadecenoic fatty acids. The structure of the lipopolysaccharide's O polysaccharide was established, with the branched octasaccharide repeating unit being represented by l-rhamnose, l-3-O-Me-rhamnose, d-galactose and d-glucuronic acid. The SR55 lipopolysaccharide induced deformations of wheat root hairs. The lipopolysaccharide was not involved in bacterial cell aggregation, but its use to pretreat wheat roots was conducive to cell adsorption. This study shows that Azospirillum bacteria can utilise their own lipopolysaccharide as a carbon source, which may give them an advantage in competitive natural environments.
Lipopolysaccharide, O-antigen, O-Polysaccharide structure, serological characterization, Azospirillum
NCBI PubMed ID: 21999541Publication DOI: 10.1134/S0006297911070108Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: room308@ibppm.sgu.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory of Biochemistry, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russia, Saratov State University, ul. Astrakhanskaya 83, 410012 Saratov, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, sugar analysis, acid hydrolysis, GLC
- 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: 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: 4973
Abronina PI, Burygin GL, Kononov LO "Synthesis of fragments of O-antigenic polysaccharides of nitrogen-fixing rhyzobacteria of the genus Azospirillum" -
Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 65(6) (2016) 1448-1463
Fragments of Oantigen polysaccharides of nitrogenfixing rhizobacteria of the genus Azospirillum isolated from natural sources may greatly vary in the monosaccharide composition, molecular weight, as well as in the presence of side chains and branching sites along the main chain. These variations, along with the differences in purity and homogeneity of the samples, hamper investigations of the role of individual components of Oantigen polysaccha rides of the rhizobacteria Azospirillum in interactions with plants, including important cereal crops. Therefore, synthetic oligosaccharides, which correspond to Oantigen polysaccharide fragments of rhizobacteria of the genus Azospirillum and have a strictly defined structure and high purity, are highly demanded. The review summarizes the data on the synthesis of these oligosaccharide fragments as promising tools for investigation of the mechanism of formation of a symbiotic association with plants.
synthesis, polysaccharides, O-antigens, fragment, nitrogen fixing, 1, Azospirillum, 2-cisglycosylation
Publication DOI: 10.1007/s11172-016-1472-2Journal NLM ID: 100912060Publisher: New York: Consultants Bureau
Correspondence: polinaabronina@yandex.ru; kononov@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, Russian Federation, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 prosp. Entuziastov, 410049 Saratov, Russian Federation
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, MS, glycosylation
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14. Compound ID: 7778
|
b-D-Glcp-(1-2)-+
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_2116141,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3464
Fedonenko YP, Zdorovenko EL, Konnova SA, Kachala VV, Ignatov VV "Structural analysis of the O-antigen of the lipopolysaccharide from Azospirillum lipoferum SR65" -
Carbohydrate Research 343(16) (2008) 2841-2844
A neutral O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide isolated by phenol/water extraction from the asymbiotic diazotrophic rhizobacterium Azospirillum lipoferum SR65. The following structure of the O-polysaccharide was established by composition and methylation analyses, Smith degradation, and 1H and 13C NMR spectroscopy, including a 2D ROESY experiment:
Lipopolysaccharide, bacterial polysaccharide structure, Azospirillum lipoferum
NCBI PubMed ID: 18561903Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E.L. Zdorovenko
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Prospekt Entuziastov 13, 410049 Saratov, Russia.
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, chemical analysis, Smith degradation
- Article ID: 3465
Fedonenko YP, Konnova ON, Zatonsky GV, Konnova SA, Shashkov AS, Zdorovenko EL, Ignatov VV, Knirel YA "Structural studies of the polysaccharides from the Azospirillum brasilense S17 lipopolysaccharide" -
Carbohydrate Research 343(4) (2008) 810-816
A mixture of two structurally distinct neutral O-polysaccharides was obtained by mild acid degradation of the lipopolysaccharideisolated by the phenol/water extraction from the asymbiotic diazotrophic rhizobacterium Azospirillum brasilense S17.The following structures of the O-polysaccharides were established by composition and methylation analyses, Smith degradation,and 1H and 13C NMR spectroscopy, including a 2D NOESY experiment: where L-Rha2Me stands for 2-O-methyl-L-rhamnose and SHb for the (S)-3-hydroxybutanoyl group. The occurrence of two distinct polysaccharides is reported for the first time in Azospirillum spp.2007 Elsevier Ltd. All rights reserved
Lipopolysaccharide, Azospirillum brasilense, bacterial polysaccharide structure, 2-O-Methyl-L-rhamnose
NCBI PubMed ID: 18226805Publication DOI: 10.1016/j.carres.2007.12.013Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E.L. Zdorovenko
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Prospekt Entuziastov 13, 410049 Saratov, Russia, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, Smith degradation, composition analysis
- Article ID: 4015
Fedonenko YP, Boyko AS, Zdorovenko EL, Konnova SA, Shashkov AS, Ignatov VV, Knirel YA "Structural pecularities of the O-specific polysaccharides of Azospirillum bacteria of serogroup III" -
Biochemistry (Moscow) 76(7) (2011) 797-802
Azospirillum brasilense SR55, isolated from the rhizosphere of Triticum durum, was classified as serogroup II on the basis of serological tests. Such serogroup affiliation is uncharacteristic of wheat-associated Azospirillum species. The lipid A of A. brasilense SR55 lipopolysaccharide contained 3-hydroxytetradecanoic, 3-hydroxyhexadecanoic, hexadecanoic and octadecenoic fatty acids. The structure of the lipopolysaccharide's O polysaccharide was established, with the branched octasaccharide repeating unit being represented by l-rhamnose, l-3-O-Me-rhamnose, d-galactose and d-glucuronic acid. The SR55 lipopolysaccharide induced deformations of wheat root hairs. The lipopolysaccharide was not involved in bacterial cell aggregation, but its use to pretreat wheat roots was conducive to cell adsorption. This study shows that Azospirillum bacteria can utilise their own lipopolysaccharide as a carbon source, which may give them an advantage in competitive natural environments.
Lipopolysaccharide, O-antigen, O-Polysaccharide structure, serological characterization, Azospirillum
NCBI PubMed ID: 21999541Publication DOI: 10.1134/S0006297911070108Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: room308@ibppm.sgu.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory of Biochemistry, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russia, Saratov State University, ul. Astrakhanskaya 83, 410012 Saratov, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, sugar analysis, acid hydrolysis, GLC
- 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: 4823
Sigida EN, Fedonenko YP, Shashkov AS, Zdorovenko EL, Konnova SA, Ignatov VV, Knirel YA "Structure of the polysaccharides from the lipopolysaccharide of Azospirillum brasilense Jm125A2" -
Carbohydrate Research 416 (2015) 37-40
Two polysaccharides were obtained by mild acid degradation of the lipopolysaccharide of associative nitrogen-fixing bacteria Azospirillum brasilense Jm125A2 isolated from the rhizosphere of a pearl millet. The following structures of the polysaccharides were established by sugar and methylation analyses, Smith degradation, and (1)H and (13)C NMR spectroscopy: [Formula: see text] Structure 1 has been reported earlier for a polysaccharide from A.?brasilense S17 (Fedonenko YP, Konnova ON, Zdorovenko EL, Konnova SA, Zatonsky GV, Shaskov AS, Ignatov VV, Knirel YA. Carbohydr Res 2008;343:810-6), whereas to our knowledge structure 2 has not been hitherto found in bacterial polysaccharides.
Lipopolysaccharide, Azospirillum brasilense, bacterial polysaccharide structure
NCBI PubMed ID: 26343325Publication DOI: 10.1016/j.carres.2015.08.011Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: si_elena@mail.ru (E.N. Sigida)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Prospekt Entuziastov 13, 410049 Saratov, Russia, Chernyshevsky Saratov State University, Ulitsa Astrakhanskaya 83, 410012 Saratov, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, GLC, mild acid hydrolysis, Smith degradation, composition analysis, 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: 4973
Abronina PI, Burygin GL, Kononov LO "Synthesis of fragments of O-antigenic polysaccharides of nitrogen-fixing rhyzobacteria of the genus Azospirillum" -
Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 65(6) (2016) 1448-1463
Fragments of Oantigen polysaccharides of nitrogenfixing rhizobacteria of the genus Azospirillum isolated from natural sources may greatly vary in the monosaccharide composition, molecular weight, as well as in the presence of side chains and branching sites along the main chain. These variations, along with the differences in purity and homogeneity of the samples, hamper investigations of the role of individual components of Oantigen polysaccha rides of the rhizobacteria Azospirillum in interactions with plants, including important cereal crops. Therefore, synthetic oligosaccharides, which correspond to Oantigen polysaccharide fragments of rhizobacteria of the genus Azospirillum and have a strictly defined structure and high purity, are highly demanded. The review summarizes the data on the synthesis of these oligosaccharide fragments as promising tools for investigation of the mechanism of formation of a symbiotic association with plants.
synthesis, polysaccharides, O-antigens, fragment, nitrogen fixing, 1, Azospirillum, 2-cisglycosylation
Publication DOI: 10.1007/s11172-016-1472-2Journal NLM ID: 100912060Publisher: New York: Consultants Bureau
Correspondence: polinaabronina@yandex.ru; kononov@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, Russian Federation, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 prosp. Entuziastov, 410049 Saratov, Russian Federation
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, MS, glycosylation
- Article ID: 5498
Sigida EN, Fedonenko YP, Shashkov AS, Toukach PV, Shelud'ko AV, Zdorovenko EL, Knirel YA, Konnova SA "Structural studies of O-specific polysaccharide(s) and biological activity toward plants of the lipopolysaccharide from Azospirillum brasilense SR8" -
International Journal of Biological Macromolecules 126 (2019) 246-253
Lipopolysaccharide (LPS) was extracted from dry bacterial cells of plant-growth-promoting bacterium Azospirillum brasilense SR8 (IBPPM 5). The O-specific polysaccharide (OPS) was obtained by mild acid hydrolysis of the lipopolysaccharide and studied by sugar analysis, 1H and 13C NMR spectroscopy, including 1H,1H COSY, TOCSY, ROESY, and 1H,13C HSQC and HMBC experiments, computational NMR-based structure analysis, and Smith degradation. The OPS was shown to contain two types of repeating units of the following structure: Both OPS structures are present in A. brasilense 54, from which structure 1 has been reported earlier (Fedonenko et al., 2011), whereas to our knowledge structure 2 has not been hitherto found in bacterial saccharides. Treatment of wheat seedling roots with LPS of A. brasilense SR8 increased the number of root hair deformations as compared to seedlings grown without LPS, but had no effect on adsorption of the bacteria to the root surface. A. brasilense SR8 was able to utilize LPS of several structurally related Azospirillum strains.
Lipopolysaccharide, structure, O-specific polysaccharide, Azospirillum brasilense, Chemotaxis, NMR simulation, Root hair deformation
NCBI PubMed ID: 30590146Publication DOI: 10.1016/j.ijbiomac.2018.12.229Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: E.N. Sigida
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospect Entuziastov, Saratov 410049, Russia, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, Russia, N. G. Chernyshevsky Saratov State University, 83 Ulitsa Astrakhanskaya, Saratov 410012, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, de-O-acylation, SDS-PAGE, sugar analysis, acid hydrolysis, GLC, GC, Smith degradation, GPC, 13C NMR analysis by GRASS, experiments on plants
- Article ID: 5846
Sigida EN, Kokoulin MS, Dmitrenok PS, Grinev VS, Fedonenko YP, Konnova SA "The Structure of the O-Specific Polysaccharide and Lipid A of the Type Strain Azospirillum rugosum DSM-19657" -
Russian Journal of Bioorganic Chemistry 46(1) (2020) 60-70
The paper reports the structural study of the lipopolysaccharide from the type strain of the soil nitrogen-fixing bacterium Azospirillum rugosum isolated from oil-polluted soils. Based on the chemical analysis and 1D- and 2D 1H and 13C NMR spectroscopy data it has been demonstrated that the O-specific polysaccharide consists of the two types of repeating units identical to those previously described for the O-specific polysaccharide of the Azospirillum brasilense strain Jm125A2. Structural analysis of the lipid A using gas-liquid chromatography (GLC) and MALDI mass spectrometry revealed the presence of penta-, tetra-, and triacylated species. The primary fatty acids in the lipid A are the N-linked 16:0(3-OH) and O-linked 14:0(3-OH). Microheterogeneity within each species arises from the presence of different secondary fatty acids (16:0, 18:1, or 19:0) acylating the 16:0(3-OH) acid of the distal GlcN ring.
Lipopolysaccharide, lipid A, NMR spectroscopy, O-specific polysaccharide, Azospirillum rugosum, MALDI mass spectrometry
Publication DOI: 10.1134/S1068162020010112Journal NLM ID: 9420101Publisher: Springer Science and Business Media
Correspondence: si_elena@mail.ru
Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 410049, Saratov, Russia, Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, 690022, Vladivostok, Russia, Chernyshevskii Saratov National Research State University, 410012, Saratov, Saratov oblast, Russia
Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, methylation, de-O-acylation, sugar analysis, acid hydrolysis, GLC, GC, MS/MS, MALDI-TOF MS, composition analysis
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15. Compound ID: 8432
|
b-D-Glcp-(1-3)-+
|
-3)-a-L-Rhap2Ac-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, CPS
Contained glycoepitopes: IEDB_130422,IEDB_133754,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_2116141,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3676
Choma A, Komaniecka I, Sowinski P "Revised structure of the repeating unit of the O-specific polysaccharide from Azospirillum lipoferum strain SpBr17" -
Carbohydrate Research 344(7) (2009) 936-939
A neutral O-polysaccharide liberated by mild acid hydrolysis of a lipopolysaccharide isolated from Azospirillum lipoferum SpBr17 was investigated using 1D and 2D (1)H and (13)C NMR spectroscopy, including HSQC, HMBC, and NOESY as well as SDS-PAGE electrophoresis along with sugar and methylation analyses. The structure of the O-specific polysaccharide repeating unit was established as follows: [Formula: see text]. The presented structure is a revised version of the formula that was published earlier in the Abstracts of the 9th International Congress on Nitrogen Fixation in Cancun (Mexico, 1992)
Lipopolysaccharide, O-antigen, Azospirillum lipoferum
NCBI PubMed ID: 19324329Publication DOI: 10.1016/j.carres.2009.02.021Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: achoma@hektor.umcs.lublin.pl
Institutions: Department of Genetics and Microbiology, Maria Curie-Sklodowska University, 19 Akademicka St., 20-033 Lublin, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, acid hydrolysis, NMR-1D, PAGE
- Article ID: 4015
Fedonenko YP, Boyko AS, Zdorovenko EL, Konnova SA, Shashkov AS, Ignatov VV, Knirel YA "Structural pecularities of the O-specific polysaccharides of Azospirillum bacteria of serogroup III" -
Biochemistry (Moscow) 76(7) (2011) 797-802
Azospirillum brasilense SR55, isolated from the rhizosphere of Triticum durum, was classified as serogroup II on the basis of serological tests. Such serogroup affiliation is uncharacteristic of wheat-associated Azospirillum species. The lipid A of A. brasilense SR55 lipopolysaccharide contained 3-hydroxytetradecanoic, 3-hydroxyhexadecanoic, hexadecanoic and octadecenoic fatty acids. The structure of the lipopolysaccharide's O polysaccharide was established, with the branched octasaccharide repeating unit being represented by l-rhamnose, l-3-O-Me-rhamnose, d-galactose and d-glucuronic acid. The SR55 lipopolysaccharide induced deformations of wheat root hairs. The lipopolysaccharide was not involved in bacterial cell aggregation, but its use to pretreat wheat roots was conducive to cell adsorption. This study shows that Azospirillum bacteria can utilise their own lipopolysaccharide as a carbon source, which may give them an advantage in competitive natural environments.
Lipopolysaccharide, O-antigen, O-Polysaccharide structure, serological characterization, Azospirillum
NCBI PubMed ID: 21999541Publication DOI: 10.1134/S0006297911070108Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: room308@ibppm.sgu.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory of Biochemistry, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russia, Saratov State University, ul. Astrakhanskaya 83, 410012 Saratov, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, sugar analysis, acid hydrolysis, GLC
- 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: 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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