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1. Compound ID: 189
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-Glcp2Ac-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144825,IEDB_144826,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
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2. Compound ID: 190
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a-L-Rhap-(1-2)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144825,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
- Article ID: 1752
Michon F, Katzenellenbogen E, Kasper DL, Jennings HJ "Structure of the complex group-specific polysaccharide of Group B Streptococcus" -
Biochemistry 26 (1987) 476-486
The group-specific antigen was isolated from a type Ia group B streptococcal strain and is a complex polysaccharide composed of α-L-rhamnopyranosyl, α-D-galactopyranosyl, 2-acetamido-2-deoxy-β-D-glucopyranosyl, D-glucitol, and phosphate residues. The complexity of the group B polysaccharide antigen is evident from the fact that when depolymerized by basic hydrolysis it yielded three structurally related, but nevertheless significantly different, oligosaccharides. These oligosaccharides were obtained in different molar quantities as their monophosphate esters. This evidence strongly suggests that they are linked by phosphodiester bonds in the original group B antigen. If these oligosaccharides are in fact randomly situated throughout the linear polysaccharide, then this type of heterogeneous repeating unit is unusual for a polysaccharide of bacterial origin. However, this structural arrangement of the oligosaccharides has yet to be unambiguously established because the alternate explanation of there being three different polysaccharides in the group B antigen cannot be discounted in the evidence presented here. The oligosaccharides were enzymatically dephosphorylated, and the structures of two of the three oligosaccharides are (formula: see text) Despite their structural differences, the two oligosaccharides are related by the smaller being an integral part of the larger. In the structural analysis of the group B antigen, methylation analysis, periodate oxidation, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, fast atom bombardment mass spectrometry, and various specific chemical and enzymatic degradations were the principal methods used. Of particular interest was the use of an α-rhamnosidase to selectively degrade the larger oligosaccharide. This facilitated the assignment of signals in its 1H and 13C NMR spectra.
NCBI PubMed ID: 3548820Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A OR6
Methods: 13C NMR, 1H NMR
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3. Compound ID: 191
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a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_136105,IEDB_144825,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
- Article ID: 1752
Michon F, Katzenellenbogen E, Kasper DL, Jennings HJ "Structure of the complex group-specific polysaccharide of Group B Streptococcus" -
Biochemistry 26 (1987) 476-486
The group-specific antigen was isolated from a type Ia group B streptococcal strain and is a complex polysaccharide composed of α-L-rhamnopyranosyl, α-D-galactopyranosyl, 2-acetamido-2-deoxy-β-D-glucopyranosyl, D-glucitol, and phosphate residues. The complexity of the group B polysaccharide antigen is evident from the fact that when depolymerized by basic hydrolysis it yielded three structurally related, but nevertheless significantly different, oligosaccharides. These oligosaccharides were obtained in different molar quantities as their monophosphate esters. This evidence strongly suggests that they are linked by phosphodiester bonds in the original group B antigen. If these oligosaccharides are in fact randomly situated throughout the linear polysaccharide, then this type of heterogeneous repeating unit is unusual for a polysaccharide of bacterial origin. However, this structural arrangement of the oligosaccharides has yet to be unambiguously established because the alternate explanation of there being three different polysaccharides in the group B antigen cannot be discounted in the evidence presented here. The oligosaccharides were enzymatically dephosphorylated, and the structures of two of the three oligosaccharides are (formula: see text) Despite their structural differences, the two oligosaccharides are related by the smaller being an integral part of the larger. In the structural analysis of the group B antigen, methylation analysis, periodate oxidation, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, fast atom bombardment mass spectrometry, and various specific chemical and enzymatic degradations were the principal methods used. Of particular interest was the use of an α-rhamnosidase to selectively degrade the larger oligosaccharide. This facilitated the assignment of signals in its 1H and 13C NMR spectra.
NCBI PubMed ID: 3548820Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A OR6
Methods: 13C NMR, 1H NMR
- Article ID: 1755
Michon F, Brisson JR, Dell A, Kasper DL, Jennings HJ "Multiantennary group-specific polysaccharide of group B Streptococcus" -
Biochemistry 27 (1988) 5341-5351
The group-specific antigen of group B Streptococcus is composed of four different oligosaccharide units of Mw 766 (III), 1277 (II), 1462 (IV), and 1788 (I). The major constituent sugars of the oligosaccharides are α-L-rhamnopyranose, α-D-galactopyranose, 2-acetamido-2-deoxy-β-D-glucopyranosyl, and D-glucitol except that III does not contain α-D-galactopyranosyl or 2-acetamido-2-deoxy-β-D-glucopyranosyl residues and IV contains no D-glucitol but has one additional β-L-rhamnopyranosyl residue. The structures of II and III have been previously elucidated [Michon, F., Katzenellenbogen, E., Kasper, D. L., & Jennings, H. J. (1987) Biochemistry 26, 476-486]. In the group B antigen all the oligosaccharides are linked by one type of phosphodiester bond from O6 of the D-glucitol residue of one oligosaccharide to O6 of the α-D-galactopyranosyl residue of the next to form a complex and highly branched multiantennary structure. However, despite the heterogeneous nature of its component oligosaccharides, some order has been identified in the biosynthesis of the group B antigen from chemical and enzymatic sequence studies. Because III lacks an α-D-galactopyranosyl residue but has a D-glucitol residue, it is situated at the reducing terminus of all the branches of the group B antigen where it is always adjacent to a II moiety. Conversely, IV has an α-D-galactopyranosyl residue but has no D-glucitol and is therefore located at the reducing terminus of the group B antigen where it probably functions as a linker molecule between the group B polysaccharide and the cell wall peptidoglycan of the group B streptococcal organisms. Oligosaccharide I contains two α-D-galactopyranosyl residues and one D-glucitol residue and thus constitutes the branch point in the group B antigen, whereas II contains one of each of the above residues and therefore is situated in linear interchain positions. The group B antigen is highly branched and probably has a unique multiantennary structure.
NCBI PubMed ID: 3048399Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario
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4. Compound ID: 1346
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-3)-b-D-Galp-(1-2)-a-L-Rhap-(1-4)-b-D-GlcpA-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_133754,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_144825,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 426
Yang BY, Montgomery R "b-Elimination of glucosyluronic residues during methylation of an acidic polysaccharide from Erwinia chrysanthemi CU 643" -
Carbohydrate Research 332(3) (2001) 317-323
The Erwinia chrysanthemi CU643 EPS has a linear hexasaccharide repeating unit in which a 4-linked uronic acid residue is present. The EPS was methylated by either the NaOH-Me2SO-MeI or Li-dimsyl procedure. MALDI-TOF MS analysis of the methylated products indicates that the beta-eliminative degradation occurs during the methylation, as characterized by serial fragments of the hexasaccharide repeating units. The degradation was clearly defined from the methylation of a glucosyluronic-containing pyruvated pentasaccharide
methylation, acidic extracellular polysaccharide, Erwinia chrysanthemi, β-elimination
NCBI PubMed ID: 11376611Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rex-montgomery@uiowa.edu
Institutions: Department of Biochemistry, College of Medicine, University of Iowa, Iowa City, Iowa, IA 52242, USA
Methods: methylation, GLC-MS, MALDI-TOF MS
- Article ID: 1304
Yun Yang B, Gray JSS, Montgomery R "Extracellular polysaccharide of Erwinia chrysanthemi CU643" -
Carbohydrate Research 316(1-4) (1999) 138-154
Erwinia chrysanthemi are gram-negative bacterial phytopathogens causing soft rots in a number of plants. The structure of the extracellular polysaccharide (EPS) produced by E. chrysanthemi strain CU643, pathogenic to Philodendron, has been determined using a combination of chemical and physical techniques including methylation analysis, high- and low-pressure gel-filtration and anion-exchange chromatography, high-pH anion-exchange chromatography, partial acid hydrolysis, mass spectrometry, and 1- and 2-D NMR spectroscopy. In contrast to the structures of the EPS reported for other strains of E. chrysanthemi, the EPS from strain CU643 is a linear polysaccharide containing L-Rhap, D-Galp, and D-GlcAp in the ratio 4:1:1. Evidence is presented for the following hexasaccharide repeat unit [see text]
structure, extracellular polysaccharide, Erwinia chrysanthemi, Philodendron
NCBI PubMed ID: 10420593Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rex-montgomery@uiowa.edu
Institutions: Department of Biochemistry, College of Medicine, University of Iowa, Iowa City 52242, USA
Methods: NMR-2D, methylation, FAB-MS, partial acid hydrolysis, NMR, MALDI-TOF MS
- 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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5. Compound ID: 1443
Structure type: polymer chemical repeating unit
Trivial name: L-rhamnan, water-soluble EPS
Compound class: EPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_144825,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 457
De Castro C, Bedini E, Garozzo D, Sturiale L, Parrilli M "Structural determination of the O-chain moieties of the lipopolysaccharide fraction from Agrobacterium radiobacter DSM 30147" -
European Journal of Organic Chemistry (18) (2004) 3842-3849
Two O-chain structures were identified after acid hydrolysis of the lipopolysaccharide fraction of Agrobacterium radiobacter (type strain). The first is constituted by the linear tetrasaccharide repeating unit [2)-a-L-Rhap-(1-3)-a-L-Rhap- (1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-]n and the second by the (1-2)-branched repeating unit a-D-Manp-(1-2)-[3)-a-DFucp-(1-3)-a-D-Fucp-(1-]n.The two structures were determined mainly by 1D- and 2D NMR spectroscopy together with chemical-degradation methods. A detailed analysis of the NOESY spectrum, supported by molecular dynamics calculations, suggested that some unexpected NOEs were due to the sum of many small dipolar effects, whose identification was possible only by considering the 3D structure of an O-chain oligosaccharide bigger than the repeating unit.
Lipopolysaccharide, NMR spectroscopy, conformational analysis, Agrobacterium, Structure determination
Publication DOI: 10.1002/ejoc.200400238Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: decastro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita` di Napoli, Complesso Universitario Monte Sante Angelo, Via Cintia 4, 80126 Napoli, Italy, Istituto di Chimica e Tecnologia dei Polimeri, CNR Viale R. Margherita 6,95123 Catania, Italy
Methods: NMR-2D, methylation, NMR, Smith degradation, MALDI-TOF MS
- 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: 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: 1316
Zdorovenko EL, Zatonsky GV, Kocharova NA, Shashkov AS, Knirel YA, Ovod V "Structures of the O-polysaccharides of two strains of Pseudomonas syringae pv. porri from genomospecies 4" -
European Journal of Biochemistry 270(1) (2003) 20-27
Strains of Pseudomonas syringae pv. porri are characterized by a number of pathovar-specific phenotypic and genomic characters and constitute a highly homogeneous group. Using monoclonal antibodies, they all were classified in a novel P. syringae serogroup O9. The O polysaccharides (OPS) isolated from the lipopolysaccharides (LPS) of P. syringae pv. porri NCPPB 3365 and NCPPB 3364T possess multiple oligosaccharide O repeats, some of which are linear and composed of l-rhamnose (l-Rha), whereas the major O repeats are branched with l-rhamnose in the main chain and GlcNAc in side chains (structures 1 and 2). Both branched O repeats, which differ in the position of substitution of one of the Rha residues and in the site of attachment of GlcNAc, were found in the two strains studied, O repeat 1 being major in strain NCPPB 3365 and 2 in strain NCPPB 3364T. [formula: see text]. The relationship between OPS chemotype and serotype on one hand and the genomic characters of P. syringae pv. porri and other pathovars delineated in genomospecies 4 on the other hand is discussed
Lipopolysaccharide, monoclonal antibody, serological classification, Pseudomonas syringae, O polysaccharide structure
NCBI PubMed ID: 12492471Journal 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, Tampere, Finland
Methods: NMR-2D, methylation, NMR, Smith degradation
- Article ID: 1452
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 1465
Knirel YA, Zdorovenko GM "Structures of O-polysaccharide chains of lipopolysaccharides as the basis for classification of Pseudomonas syringae and related strains" -
Book: Pseudomonas Syringae Pathovars and Related Pathogens (series: Developments in Plant Pathology) (1997) 475-480
The O-polysaccharides of various serogroups of P. syringae were found to have similar structures with the main chain of a rhamnan which may carry a monosaccharide side chain of D-rhamnose, D-fucose, 2-acetamido-2-deoxy-D-glucose or 3-acetamido-3,6-dideoxy-D-galactose. The relationship between the serological specificity and the host-plant specificity of P. syringae and the structures of the O-polysaccharides is discussed.
Lipopolysaccharide, structure, O-antigen, O-polysaccharide, serological specificity, Pseudomonas syringae, Serogrouping, Host-plant specificity
Publication DOI: 10.1007/978-94-011-5472-7_85Publisher: Springer Netherlands
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead D, Vivian A, von Kietzell J
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Leninsky Pr. 47, Moscow B-334, Russia, D.K. Zabolotny Institute of Microbiology and Virology, Zabolotnogo 154, Kiev-143, Ukraine
- Article ID: 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: 3457
De Castro C, Molinaro A, Lanzetta R, Silipo A, Parrilli M "Lipopolysaccharide structures from Agrobacterium and Rhizobiaceae species" -
Carbohydrate Research 343(12) (2008) 1924-1933
This review reports and discusses the structural and the biological data available for the lipopolysaccharides from the Gram-negative bacterium Agrobacterium together with those of other related Rhizobiaceae species
Lipopolysaccharide, Rhizobium, symbiosis, Agrobacterium, Tumor induction
NCBI PubMed ID: 18353297Publication DOI: 10.1016/j.carres.2008.01.036Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: decastro@unina.it; molinaro@unina.it
Institutions: Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario Monte Sant' Angelo, Via Cinthia 4, 80126 Napoli, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, MS, composition analysis, NMR-1D
- 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: 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
- 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: 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: 6029
Bellich B, Jou IA, Buriola C, Ravenscroft N, Brady JW, Fazli M, Tolker-Nielsen T, Rizzo R, Cescutti P "The biofilm of Burkholderia cenocepacia H111 contains an exopolysaccharide composed of l-rhamnose and l-mannose: Structural characterization and molecular modelling" -
Carbohydrate Research 499 (2021) 108231
Burkholderia cenocepacia belongs to the Burkholderia Cepacia Complex, a group of 22 closely related species both of clinical and environmental origin, infecting cystic fibrosis patients. B. cenocepacia accounts for the majority of the clinical isolates, comprising the most virulent and transmissible strains. The capacity to form biofilms is among the many virulence determinants of B. cenocepacia, a characteristic that confers enhanced tolerance to some antibiotics, desiccation, oxidizing agents, and host defenses. Exopolysaccharides are a major component of biofilm matrices, particularly providing mechanical stability to biofilms. Recently, a water-insoluble exopolysaccharide produced by B. cenocepacia H111 in biofilm was characterized. In the present study, a water-soluble exopolysaccharide was extracted from B. cenocepacia H111 biofilm, and its structure was determined by GLC-MS, NMR and ESI-MS. The repeating unit is a linear rhamno-tetrasaccharide with 50% replacement of a 3-α-L-Rha with a α-3-L-Man. [2)-α-L-Rhap-(1→3)-α-L-[Rhap or Manp]-(1→3)-α-L-Rhap-(1→2)-α-L-Rhap-(1→]n Molecular modelling was used to obtain information about local structural motifs which could give information about the polysaccharide conformation.
NMR, molecular modelling, polysaccharide structure, Biofilm, Burkholderia cenocepacia H111, L-mannose
NCBI PubMed ID: 33440288Publication DOI: 10.1016/j.carres.2020.108231Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Paola Cescutti
Institutions: Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa, Department of Life Sciences, University of Trieste, Via L. Giorgieri 1, Bdg. C11, 34127, Trieste, Italy, Department of Food Science, Cornell University, Ithaca, NY, 14853, USA, Costerton Biofilm Center, Department of Immunology and Microbiology, Faculty of Health and Medical Sciences, University of Copenhagen, Blegdamsvej 3B, 2200, Copenhagen, Denmark
Methods: 13C NMR, 1H NMR, NMR-2D, GLC-MS, partial acid hydrolysis, ESI-MS, GLC, MD simulations, composition analysis
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6. Compound ID: 1738
|
b-D-GlcpNAc-(1-2)-+
|
-2)-a-L-Rhap-(1-2)-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_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_143253,IEDB_144825,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 536
Ma Z, Zhang J, Kong F "A concise synthesis of two isomeric pentasaccharides, the O repeat units from the lipopolysaccharides of P. syringae pv. porri NCPPB 3364(T) and NCPPB 3365" -
Carbohydrate Research 339(1) (2004) 43-49
A concise synthesis of two isomeric pentasaccharides, α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-[β-D-GlcpNAc-(1→2)]-α-L-Rhap (A) and α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-[β-D-GlcpNAc-(1→2)]-α-L-Rhap-(1→3)-α-L-Rhap (B), the O repeats from the lipopolysaccharides of Pseudonomonas syringae pv. porri NCPPB 3364(T) and 3365 was achieved via assembly of the building blocks, allyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside (1), 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (2), allyl 4-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside (6), 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (7), and allyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside (10). Coupling of 1 with 2 followed by deallylation and trichloroacetimidate formation gave the disaccharide donor 5, while condensation of 6 with 7, followed by dechloroacetylation, offered the disaccharide acceptor 9. Then, 5 was coupled with 10 to obtain the trisaccharide 11, and subsequent deallylation and trichloroacetimidate formation furnished the trisaccharide donor 13. Coupling of 9 with 13, followed by deprotection, afforded pentasaccharide 19, while condensation of 9 with 5, followed by deallylation and trichloroacetimidate formation, gave the tetrasaccharide donor 16, whose coupling with 10 and subsequent deprotection yielded another pentasaccharide 22
oligosaccharide, rhamnose, Glucosamine
NCBI PubMed ID: 14659670Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: fzkong@mail.rcees.ac.cn
Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, Chinese Academy of Sciences, P.O. Box 2871, Beijing 100085, China
- Article ID: 1316
Zdorovenko EL, Zatonsky GV, Kocharova NA, Shashkov AS, Knirel YA, Ovod V "Structures of the O-polysaccharides of two strains of Pseudomonas syringae pv. porri from genomospecies 4" -
European Journal of Biochemistry 270(1) (2003) 20-27
Strains of Pseudomonas syringae pv. porri are characterized by a number of pathovar-specific phenotypic and genomic characters and constitute a highly homogeneous group. Using monoclonal antibodies, they all were classified in a novel P. syringae serogroup O9. The O polysaccharides (OPS) isolated from the lipopolysaccharides (LPS) of P. syringae pv. porri NCPPB 3365 and NCPPB 3364T possess multiple oligosaccharide O repeats, some of which are linear and composed of l-rhamnose (l-Rha), whereas the major O repeats are branched with l-rhamnose in the main chain and GlcNAc in side chains (structures 1 and 2). Both branched O repeats, which differ in the position of substitution of one of the Rha residues and in the site of attachment of GlcNAc, were found in the two strains studied, O repeat 1 being major in strain NCPPB 3365 and 2 in strain NCPPB 3364T. [formula: see text]. The relationship between OPS chemotype and serotype on one hand and the genomic characters of P. syringae pv. porri and other pathovars delineated in genomospecies 4 on the other hand is discussed
Lipopolysaccharide, monoclonal antibody, serological classification, Pseudomonas syringae, O polysaccharide structure
NCBI PubMed ID: 12492471Journal 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, Tampere, Finland
Methods: NMR-2D, methylation, NMR, Smith degradation
- 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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7. Compound ID: 1775
|
b-D-GlcpNAc-(1-3)-+
|
-2)-a-L-Rhap-(1-2)-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_131174,IEDB_133754,IEDB_135610,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_144825,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 555
Barone G, Bedini E, Unverzagt C, Parilli M "Synthesis of the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010" -
Carbohydrate Research 339(2) (2004) 393-400
The synthesis of the repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010 is reported. The strategy used was based on the successive coupling of a trisaccharide rhamnosyl trichloroacetimidate with a rhamnosyl acceptor with a free hydroxyl group on C-2. The pentasaccharide was then obtained by coupling with a N-Troc-tri-O-acetyl-glucosamine trichloroacetimidate. The synthesis allowed the oligomerisation of the repeating unit.
repeating unit, Oligosaccharides, O-chain, glycosylation, Pseudomonas ribicola
NCBI PubMed ID: 14698898Publication DOI: 10.1016/j.carres.2003.10.002Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: parrilli@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli ''Federico II'', Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy, Bioorganische Chemie, Gebaude NWI, Universitat Bayreuth,95440 Bayreuth, Germany
- 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: 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: 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: 5461
Knirel YA, Naumenko OI, Senchenkova SN, Perepelov AV "Chemical methods for selective cleavage of glycosidic linkages in structural analysis of bacterial polysaccharides" -
Russian Chemical Reviews = Uspekhi Khimii 88(4) (2019) 406-424
This review is devoted to methods for the selective cleavage of glycosidic bonds. The mechanisms of reactions underlying these methods are considered and examples of their practical application in the structural analysis of bacterial polysaccharides are given. Specific methods for the selective cleavage of polysaccharides, remaining relevant for researchers, include the Smith degradation based on destruction of monosaccharides containing vicinal diol groups, dephosphorylation of phosphate-containing polysaccharides with hydrofluoric acid and the hydrolytic cleavage of glycosyl phosphate bonds in the latter compounds. Non-specific methods, including partial acid hydrolysis, acetolysis and solvolysis with anhydrous organic (CF3SO3H, MeSO3H, CF3CO2H) and inorganic (HF) acids do not make any specific demands on the composition and structure of the polysaccharide and are sensitive to its fine structural features. The review addesses the issue of stability of glycosidic bonds in various monosaccharides to reagents used for non-specific selective cleavage.
structural analysis, Bacterial polysaccharide, selective cleavage, glycosidic bond
Publication DOI: 10.1070/RCR4856Journal NLM ID: 0404506Publisher: London: Chemical Society
Correspondence: Yu.A. Knirel
Institutions: N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
Methods: partial acid hydrolysis, HF solvolysis, acid hydrolysis, mild acid hydrolysis, alkaline degradation, b-elimination, Smith degradation, deamination, de-O-acetylation, HF treatment, reduction with NaBD4, triflic acid solvolysis, acetolysis, Li/ethylenediamine degradation, hydrazinolysis, reduction with NaBH4, mild acid degradation, trifluoroacetic acid solvolysis, partial solvolysis with anhydrous trifluoroacetic acid, de-N-acetylation with hydrazine, part acid hydrolysis, HF solvolysis; published polymerization frame was shifted for conformity with other records.
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8. Compound ID: 1776
|
b-D-GlcpNAc-(1-3)-+
|
a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-7)-Bn |
Show graphically |
Structure type: oligomer
Trivial name: repeating unit of the O-polysaccharide
Contained glycoepitopes: IEDB_131174,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_144825,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 555
Barone G, Bedini E, Unverzagt C, Parilli M "Synthesis of the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010" -
Carbohydrate Research 339(2) (2004) 393-400
The synthesis of the repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010 is reported. The strategy used was based on the successive coupling of a trisaccharide rhamnosyl trichloroacetimidate with a rhamnosyl acceptor with a free hydroxyl group on C-2. The pentasaccharide was then obtained by coupling with a N-Troc-tri-O-acetyl-glucosamine trichloroacetimidate. The synthesis allowed the oligomerisation of the repeating unit.
repeating unit, Oligosaccharides, O-chain, glycosylation, Pseudomonas ribicola
NCBI PubMed ID: 14698898Publication DOI: 10.1016/j.carres.2003.10.002Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: parrilli@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli ''Federico II'', Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy, Bioorganische Chemie, Gebaude NWI, Universitat Bayreuth,95440 Bayreuth, Germany
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9. Compound ID: 1833
|
a-D-Fucp3NAc-(1-4)-+
|
-2)-a-L-Rhap-(1-2)-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_144825,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: 1312
Zdorovenko EL, Ovod V, Shashkov AS, Kocharova NA, Knirel YA, Krohn K "Structure of the O-polysaccharide of the lipopolysaccharide of Pseudomonas syringae pv. garcae ICMP 8047" -
Biochemistry (Moscow) 64(7) (1999) 765-773
The composition and structure of the O-polysaccharide of the lipopolysaccharide of Pseudomonas syringae pathovar garcae ICMP 8047 were studied using methylation analyses, Smith degradation, and 1H- and 13C NMR spectroscopy, including two-dimensional correlation spectroscopy (COSY), total correlation spectroscopy (TOCSY), nuclear Overhauser effect spectroscopy (NOESY), and H-detected 1H,13C heteronuclear multiple-quantum coherence (HMQC) experiments. The polysaccharide was found to contain L-rhamnose and 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc) in the ratio 4:1 and to consist of two types of pentasaccharide repeating units. The major (1) and minor (2) repeating units differ from each other only in the position of substitution of one of the rhamnose residues in the main chain. Similar structural heterogeneity has been reported formerly in O-polysaccharides of some other P. syringae strains having a similar monosaccharide composition. A Fuc3NAc residue is attached to the main rhamnan chain as a side chain by a (α1→4) glycosidic linkage; this has not hitherto been described in P. syringae: [figure].
Lipopolysaccharide, O-specific polysaccharide, 6-dideoxy-D-galactose, 3-Acetamido-3, Pseudomonas syringae, structural heterogeneity
NCBI PubMed ID: 10424899Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR-2D, methylation, NMR, Smith degradation
- Article ID: 1315
Zdorovenko EL, Zatonsky GV, Kocharova NA, Shashkov AS, Knirel YA, Ovod V "Structure of the O-polysaccharide of Pseudomonas syringae pv. delphinii NCPPB 1879T having side chains of 3-acetamido-3,6-dideoxy-D-galactose residues" -
Biochemistry (Moscow) 67(5) (2002) 558-565
The O-polysaccharide (OPS) was obtained from the lipopolysaccharide of Pseudomonas syringae pv. delphinii NCPPB 1879(T) and studied by sugar and methylation analyses, Smith degradation, and (1)H- and (13)C-NMR spectroscopy. The OPS was found to contain residues of L-rhamnose (L-Rha) and 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc), and the following structure of the major (n = 2) and minor (n = 3) heptasaccharide repeating units of the OPS was established: [carbohydrate structure: see text]. The OPS is distinguished by the presence of oligosaccharide side chains consisting of three D-Fuc3NAc residues that are connected to each other by the (α 1→2)-linkage. The OPS is characterized by a structural heterogeneity due to a different position of substitution of one of the four L-rhamnose residues in the main chain of the repeating unit as well as to the presence of oligosaccharide units with an incomplete side chain
Lipopolysaccharide, O-specific polysaccharide, 6-dideoxy-D-galactose, 3-Acetamido-3, Pseudomonas syringae
NCBI PubMed ID: 12059776Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, 33101 Tampere, P.O. Box 607, Finland, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia 2Institute of Medical Technology, University of Tampere, 33101 Tampere, P.O. Box 607, Finland
Methods: NMR-2D, methylation, NMR, Smith degradation
- Article ID: 1316
Zdorovenko EL, Zatonsky GV, Kocharova NA, Shashkov AS, Knirel YA, Ovod V "Structures of the O-polysaccharides of two strains of Pseudomonas syringae pv. porri from genomospecies 4" -
European Journal of Biochemistry 270(1) (2003) 20-27
Strains of Pseudomonas syringae pv. porri are characterized by a number of pathovar-specific phenotypic and genomic characters and constitute a highly homogeneous group. Using monoclonal antibodies, they all were classified in a novel P. syringae serogroup O9. The O polysaccharides (OPS) isolated from the lipopolysaccharides (LPS) of P. syringae pv. porri NCPPB 3365 and NCPPB 3364T possess multiple oligosaccharide O repeats, some of which are linear and composed of l-rhamnose (l-Rha), whereas the major O repeats are branched with l-rhamnose in the main chain and GlcNAc in side chains (structures 1 and 2). Both branched O repeats, which differ in the position of substitution of one of the Rha residues and in the site of attachment of GlcNAc, were found in the two strains studied, O repeat 1 being major in strain NCPPB 3365 and 2 in strain NCPPB 3364T. [formula: see text]. The relationship between OPS chemotype and serotype on one hand and the genomic characters of P. syringae pv. porri and other pathovars delineated in genomospecies 4 on the other hand is discussed
Lipopolysaccharide, monoclonal antibody, serological classification, Pseudomonas syringae, O polysaccharide structure
NCBI PubMed ID: 12492471Journal 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, Tampere, Finland
Methods: NMR-2D, methylation, NMR, Smith degradation
- Article ID: 1452
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 3968
Zdorovenko GM, Zdorovenko EL "Pseudomonas syringae lipopolysaccharides: Immunochemical characteristics and structure as a basis for strain classification" -
Mikrobiologiia = Microbiology [Russian] 79(1) (2010) 47-57
Lipopolysaccharide (LPS) preparations of 34 Pseudomonas syringae strains of 19 pathovars were prepared by saline extraction from wet cells and purified by repeated ultracentrifugation. The preparations reacted with homologous O-antisera, obtained by rabbit immunization with heat-killed bacterial cells. Through inhibition of homologous reactions between LPS preparations of heterologous strains (enzyme immunoassay, EIA), it was established for the first time that high serological affinity between strains is observed only if their LPS contains O-specific polysaccharide chains (OPS) comprised of completely identical rather than partially similar units. The central linear part of the OPS was found to be serologically inert when shielded with side groups. Data on immunochemical characteristics of the LPS and OPS structure are analyzed in relation to the design of P. syringae classification scheme.
Lipopolysaccharide, structure, O-specific polysaccharide, Pseudomonas syringae, classification, immunochemistry
NCBI PubMed ID: 20411661Publication DOI: 10.1134/S0026261710010078Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: evelina@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kyiv, 03143 Ukraine
Methods: partial acid hydrolysis, EIA, serological methods, de-N-acetylation/deamination
Expand this compound
Collapse this compound
10. Compound ID: 1837
|
a-D-Fucp3NAc-(1-3)-+
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-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_144825,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: 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: 1249
Spitali M, Smith ARW "Structure of the lipopolysaccharide side-chain of Pseudomonas syringae pv. tomato strain GFBP 2545 in relation to O-serotype" -
Phytopathologische Zeitschrift = Journal of Phytopathology 148(11-12) (2000) 555-561
The side-chain from the lipopolysaccharide (LPS) of Pseudomonas syringae pv. tomato strain CFBP 2545 contained L-rhamnose. By 1H- and 13C-nuclear magnetic resonance spectroscopy, methylation analysis and Smith degradation, the polysaccharide was shown to be a backbone composed of 2,3)-a-L-Rhap(1-, 2)-a-L-Rhap(1-, and 3)-a-L-Rhap(1- residues with N-acetyl-fucosamine as a branch residue, primarily of the following structure: [formula: see text]. An oligosaccharide of the following probable structure: [formula: see text] comprising 28+ACU- of the total carbohydrate was unexpectedly recovered from the side-chain during the course of Smith degradation. The polysaccharide differed from the side-chains of LPSs from P. syringae pv. tomato strains 140(R) and GSPB 483. The side-chain structure is correlated with a previously proposed sero-grouping system.
Lipopolysaccharide, structure, strain, Pseudomonas, side chain, Pseudomonas syringae, O-serotype, Pseudomonas syringae pv. tomato, ide-chain structure
Publication DOI: 10.1111/j.1439-0434.2000.00574.xJournal NLM ID: 9875585Publisher: Berlin: Parey
Institutions: School of Chemical and Life Sciences, University of Greenwich, London SE18 6PF, UK
Methods: 13C NMR, 1H NMR, methylation, 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: 1315
Zdorovenko EL, Zatonsky GV, Kocharova NA, Shashkov AS, Knirel YA, Ovod V "Structure of the O-polysaccharide of Pseudomonas syringae pv. delphinii NCPPB 1879T having side chains of 3-acetamido-3,6-dideoxy-D-galactose residues" -
Biochemistry (Moscow) 67(5) (2002) 558-565
The O-polysaccharide (OPS) was obtained from the lipopolysaccharide of Pseudomonas syringae pv. delphinii NCPPB 1879(T) and studied by sugar and methylation analyses, Smith degradation, and (1)H- and (13)C-NMR spectroscopy. The OPS was found to contain residues of L-rhamnose (L-Rha) and 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc), and the following structure of the major (n = 2) and minor (n = 3) heptasaccharide repeating units of the OPS was established: [carbohydrate structure: see text]. The OPS is distinguished by the presence of oligosaccharide side chains consisting of three D-Fuc3NAc residues that are connected to each other by the (α 1→2)-linkage. The OPS is characterized by a structural heterogeneity due to a different position of substitution of one of the four L-rhamnose residues in the main chain of the repeating unit as well as to the presence of oligosaccharide units with an incomplete side chain
Lipopolysaccharide, O-specific polysaccharide, 6-dideoxy-D-galactose, 3-Acetamido-3, Pseudomonas syringae
NCBI PubMed ID: 12059776Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, 33101 Tampere, P.O. Box 607, Finland, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia 2Institute of Medical Technology, University of Tampere, 33101 Tampere, P.O. Box 607, Finland
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: 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: 1856
Knirel YA, Zdorovenko GM, Shashkov AS, Mamyan SS, Gubanova NY, Yakovleva LM, Solyanik LP "Antigenic polysaccharides of bacteria. 30. Structure of the polysaccharide chain of the Pseudomonas syringae pv. syringae 281 (serogroup I) lipopolysaccharide" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14(2) (1988) 180-186
Anomeric methyl 3-O-(D-mannopyranosyl- and L-rhamnopyranosyl)-β-D-talopyranosides were synthesised by the stereoselective 1,2-cis- and 1,2-trans manno- and rhamnosylation of methyl 2,4,6-tri-O-acetyl-β-D-talopyranoside, which has been prepared from methyl β-D-galactopyranoside by a synthetic scheme including conversion of the C2 configuration. From 13C-NMR spectra of the disaccharides obtained the spectral alpha- and beta-effects of O3-glycosylation of talopyranose were determined.
NCBI PubMed ID: 2454629Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia
Methods: 13C NMR, 1H NMR
- Article ID: 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: 3743
Molinaro A, Newman M, Lanzetta R, Parrilli M "The structures of lipopolysaccharides from plant-associated Gram-negative bacteria" -
European Journal of Organic Chemistry 2009(34) (2009) 5887-5896
Gram-negative bacterial lipopolysaccharides (LPSs) have multiple roles in plant-microbe interactions. LPSs contribute to the low permeabilities of bacterial outer membranes, which act as barriers to protect bacteria from plant-derived antimicrobial substances. Conversely, perception of LPSs by plant cells can lead to the triggering of defence responses or to the priming of the plant to respond more rapidly and/or to a greater degree to subsequent pathogen challenge. LPSs are thus key molecules in the interactions between bacteria and plants, either in symbiosis or pathogenesis. Since LPSs are glycoconjugates genetically and chemically consisting of three different molecular regions, their detailed structure elucidation is a very topical and major scientific task for chemists, and is achieved by a combination of state-of-art chemical and spectroscopic techniques. Knowledge of LPSs' chemical structures is an important prerequisite for any further understanding of the biological processes in plant-microbe interactions. Moreover, the LPSs from Gram-negative bacteria - especially those originating from plant-associated bacteria - are a great source of novel monosaccharides with unusual and occasionally astounding chemical structures, never found in the eukaryotic world. This review presents the structures of LPSs from plant-associated bacteria isolated and identified from 2001 onwards.
lipopolysaccharides, structure elucidation, glycolipids, innate immunity, immunochemistry, plant-associated bacteria
Publication DOI: 10.1002/ejoc.200900682Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: molinaro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli “Federico II”, via Cinthia 4, 80126 Napoli, Italy, Fax: +39-081-674393, Faculty of Life Sciences, Department of Plant Biology & Biotechnology, University of Copenhagen, 1871 Frederiksberg, Denmark
- Article ID: 3968
Zdorovenko GM, Zdorovenko EL "Pseudomonas syringae lipopolysaccharides: Immunochemical characteristics and structure as a basis for strain classification" -
Mikrobiologiia = Microbiology [Russian] 79(1) (2010) 47-57
Lipopolysaccharide (LPS) preparations of 34 Pseudomonas syringae strains of 19 pathovars were prepared by saline extraction from wet cells and purified by repeated ultracentrifugation. The preparations reacted with homologous O-antisera, obtained by rabbit immunization with heat-killed bacterial cells. Through inhibition of homologous reactions between LPS preparations of heterologous strains (enzyme immunoassay, EIA), it was established for the first time that high serological affinity between strains is observed only if their LPS contains O-specific polysaccharide chains (OPS) comprised of completely identical rather than partially similar units. The central linear part of the OPS was found to be serologically inert when shielded with side groups. Data on immunochemical characteristics of the LPS and OPS structure are analyzed in relation to the design of P. syringae classification scheme.
Lipopolysaccharide, structure, O-specific polysaccharide, Pseudomonas syringae, classification, immunochemistry
NCBI PubMed ID: 20411661Publication DOI: 10.1134/S0026261710010078Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: evelina@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kyiv, 03143 Ukraine
Methods: partial acid hydrolysis, EIA, serological methods, de-N-acetylation/deamination
- Article ID: 4306
Greenfield LK, Whitfield C "Synthesis of lipopolysaccharide O-antigens by ABC transporter-dependent pathways" -
Carbohydrate Research 356 (2012) 12-24
The O-polysaccharide (O-PS; O-antigen) of bacterial lipopolysaccharides is made up of repeating units of one or more sugar residues and displays remarkable structural diversity. Despite the structural variations, there are only three strategies for O-PS assembly. The ATP-binding cassette (ABC)-transporter-dependent mechanism of O-PS biosynthesis is widespread. The Escherichia coli O9a and Klebsiella pneumoniae O2a antigens provide prototypes, which are distinguished by the fine details that link glycan polymerization and chain termination at the cytoplasmic face of the inner membrane to its export via the ABC transporter. Here, we describe the current understanding of these processes. Since glycoconjugate assembly complexes that utilize an ABC transporter-dependent pathway are widespread among the bacterial kingdom, the models described here are expected to extend beyond O-PS biosynthesis systems
Lipopolysaccharide, O-polysaccharide, ATP-binding cassette transporter, Escherichia coli O9a, Klebsiella pneumoniae O2a
NCBI PubMed ID: 22475157Publication DOI: 10.1016/j.carres.2012.02.027Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: C. Whitfield
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada N1G 2W1
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11. Compound ID: 1864
|
-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: rhamnan backbone
Compound class: O-polysaccharide, O-antigen, cell wall polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_144825,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 601
Ansaruzzaman M, Albert MJ, Holme T, Jansson P, Rahman MM, Widmalm G "A Klebsiella pneumoniae strain that shares a type-specific antigen with Shigella flexneri serotype 6. Characterization of the strain and structural studies of the O-antigenic polysaccharide" -
European Journal of Biochemistry 237 (1996) 786-791
A strain of Klebsiella pneumoniae was found as the only isolate with pathogenic potential from the stool of a two-year old patient with diarrhoea. A strong serological cross-reactivity with Shigella flexneri serotype 6 was demonstrated. The cross-reacting antigens were shown to reside in the cell wall lipopolysaccharide. Studies of the pathogenic potential of the Klebsiella strain showed low level of invasion of HEp-2 cells. However, tests for adherence to HEp-2 cells as well as tests for toxin production were negative. The strain had several small plasmids and was multidrug resistant. These data do not form a sufficient basis for estimating the pathogenic potential of the organism. No K antigen was detected. The structure of the O-antigenic polysaccharide from the K. pneumoniae strain was investigated using methylation analysis, NMR spectroscopy, and Smith degradation as the principal methods. The O-antigenic polysaccharide has the following pentasaccharide repeating unit: -3)aLRhap(1-3)aLRhap(1-2)aLRhap(1-2)aLRhap(1-2)aLRhap(1-. This structure is not identical to any of the previously described O-antigens of K. pneumoniae. The strong serological cross-reactivity with the Shigella flexneri serotype 6 O-antigen can most likely be attributed to the structural element a-L-Rhap-(l→2)-a-L-Rhap present in the O-polysaccharide repeating unit of this serotype. Antiserum raised against the K. pneumoniae strain also agglutinated S. dysenteriae serotype 1 and strains of all different serotypes of S. flexneri. The Shigella strains contain the structural element a-L-Rhap-(l→3)-a-L-Rhap in their O-antigen polysaccharides which may be responsible for the observed cross-reactivity.
Lipopolysaccharide, antigen, O-antigenic polysaccharide, Shigella flexneri, Klebsiella pneumoniae, type-specific
NCBI PubMed ID: 8647126Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, International Centre for Diarrhoeal Disease Research, Dhaka, Bangladesh, Microbiology and Tumor Biology Center, Karolinska Institute, Stockholm, Sweden, Clinical Research Centre, Analytical Unit, Karolinska Institute, Novum, Huddinge Hospital, Huddinge, Sweden
Methods: methylation, GLC-MS, NMR, SDS-PAGE, ELISA, Smith degradation, agglutination, invasion assays, plasmid analysis
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 6239
Guérin H, Kulakauskas S, Chapot-Chartier MP "Structural variations and roles of rhamnose-rich cell wall polysaccharides in Gram-positive bacteria" -
Journal of Biological Chemistry 298(10) (2022) 102488
Rhamnose-rich cell wall polysaccharides (Rha-CWPSs) have emerged as crucial cell wall components of numerous Gram-positive, ovoid-shaped bacteria-including streptococci, enterococci, and lactococci-of which many are of clinical or biotechnological importance. Rha-CWPS are composed of a conserved polyrhamnose backbone with side-chain substituents of variable size and structure. Because these substituents contain phosphate groups, Rha-CWPS can also be classified as polyanionic glycopolymers, similar to wall teichoic acids, of which they appear to be functional homologs. Recent advances have highlighted the critical role of these side-chain substituents in bacterial cell growth and division, as well as in specific interactions between bacteria and infecting bacteriophages or eukaryotic hosts. Here, we review the current state of knowledge on the structure and biosynthesis of Rha-CWPS in several ovoid-shaped bacterial species. We emphasize the role played by multicomponent transmembrane glycosylation systems in the addition of side-chain substituents of various sizes as extracytoplasmic modifications of the polyrhamnose backbone. We provide an overview of the contribution of Rha-CWPS to cell wall architecture and biogenesis and discuss current hypotheses regarding their importance in the cell division process. Finally, we sum up the critical roles that Rha-CWPS can play as bacteriophage receptors or in escaping host defenses, roles that are mediated mainly through their side-chain substituents. From an applied perspective, increased knowledge of Rha-CWPS can lead to advancements in strategies for preventing phage infection of lactococci and streptococci in food fermentation and for combating pathogenic streptococci and enterococci.
polysaccharide, cell wall, rhamnose, teichoic acid, bacteriophage, rhamnan, gram-positive bacteria, antibiotic development, multicomponent glycosylation system, ovoid-shaped, T-C fold glycosyltransferase
NCBI PubMed ID: 36113580Publication DOI: 10.1016/j.jbc.2022.102488Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: M.P. Chapot-Chartier
Institutions: Université Paris-Saclay, INRAE, AgroParisTech, Micalis Institute, Jouy-en-Josas, France
- Article ID: 6289
Palusiak A "Proteus mirabilis and Klebsiella pneumoniae as pathogens capable of causing co-infections and exhibiting similarities in their virulence factors" -
Frontiers in Cellular and Infection Microbiology 12 (2022) 991657
The genera Klebsiella and Proteus were independently described in 1885. These Gram-negative rods colonize the human intestinal tract regarded as the main reservoir of these opportunistic pathogens. In favorable conditions they cause infections, often hospital-acquired ones. The activity of K. pneumoniae and P. mirabilis, the leading pathogens within each genus, results in infections of the urinary (UTIs) and respiratory tracts, wounds, bacteremia, affecting mainly immunocompromised patients. P. mirabilis and K. pneumoniae cause polymicrobial UTIs, which are often persistent due to the catheter biofilm formation or increasing resistance of the bacteria to antibiotics. In this situation a need arises to find the antigens with features common to both species. Among many virulence factors produced by both pathogens urease shows some structural similarities but the biggest similarities have been observed in lipids A and the core regions of lipopolysaccharides (LPSs). Both species produce capsular polysaccharides (CPSs) but only in K. pneumoniae these antigens play a crucial role in the serological classification scheme, which in Proteus spp. is based on the structural and serological diversity of LPS O-polysaccharides (OPSs). Structural and serological similarities observed for Klebsiella spp. and Proteus spp. polysaccharides are important in the search for the cross-reacting vaccine antigens.
Lipopolysaccharide, core oligosaccharide, Proteus mirabilis, Klebsiella pneumoniae, virulence factors
NCBI PubMed ID: 36339335Publication DOI: 10.3389/fcimb.2022.991657Journal NLM ID: 101585359Publisher: Lausanne: Frontiers Media SA
Correspondence: A. Palusiak
Institutions: Laboratory of General Microbiology, Department of Biology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Łódź, Łódź, Poland
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12. Compound ID: 2012
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-6)-a-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_141807,IEDB_144825,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 619
Aucken HM, Wilkinson SG, Pitt TL "Re-evaluation of the serotypes of Serratia marcescens and separation into two schemes based on lipopolysaccharide (O) and capsular polysaccharide (K) antigens" -
Microbiology 144 (1998) 639-653
Chemical and serological analysis has revealed that many of the 29 O serotype reference strains of Serratia marcescens contain both neutral and acidic polysaccharides which correspond to LPS O antigens and capsular K antigens, respectively. New O and K antigen typing schemes have therefore been devised, based on the known chemical structures of the surface polysaccharides of the organism. These schemes were designed to allow the specific detection of these antigens on unknown strains using ELISAs. O antigens were detected using whole cells cultured in broth then autoclaved to remove capsular material, while K antigens were detected using formolized whole cells which had been cultured on glycerol agar to enhance capsule production. After testing with the 29 reference strains as well as 423 distinct clinical strains, it was apparent that different aspects of chemical structure were associated with different degrees of serological reactivity and the typing schemes were modified further to accommodate this. In general, the O antigen repeating unit structures were chemically simple with di- or trisaccharide backbones. Serological specificity was often provided solely by the presence or absence of an O-acetyl substituent, or a change in the linkage between two sugar residues. Five of the O serotypes in the new scheme were represented by 12 of the 29 reference strains, while three reference strains lacked O antigens altogether, resulting in the elimination of 10 of the original O types. In contrast, the K antigen repeating unit structures were more complex and chemically diverse, having at least four sugar residues. Three K types were each seen in two reference strains while 12 of the 29 reference strains were acapsular. Thus, the resulting schemes contain 19 O types and 14 K types and allow the definitive serotype identification of S. marcescens.
Lipopolysaccharide, antigen, LPS, structure, K-antigen, O-antigen, capsular polysaccharide, Serratia marcescens, Serratia, serotyping, O-serotype
NCBI PubMed ID: 9534235Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: haucken@phls.co.uk
Institutions: Laboratory of Hospital Infection, Central Public Health Laboratory, 61 Colindale Avenue, London NW9 5HT, UK, School of Chemistry, The University, Hull HU6 7RX, UK
Methods: NMR, SDS-PAGE, ELISA, chromatography, Quellung reaction, serum adsorption assays
- Article ID: 2151
Oxley D, Wilkinson SG "Structure of a neutral polymer isolated from the lipopolysaccharide of the reference strain for Serratia marcescens serogroup O18" -
Carbohydrate Research 195 (1989) 111-115
A neutral polymer (the putative O antigen) has been isolated from the lipopolysaccharide of the reference strain for Serratia marcescens serogroup 018. From the results of spectroscopic and degradative studies, the repeating unit of the polymer was identified as a linear tetrasaccharide having the structure shown. →2)-α-L-Rhap-(1→2)-α-L-Rhap-(1→6)-α-D-GlcpNAc-(1→.
NCBI PubMed ID: 2699830Publication DOI: 10.1016/0008-6215(89)85093-1Journal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Chemistry, The University, Hull (Great Britain)
- Article ID: 2193
Oxley D, Wilkinson SG "Structure of an acidic glycan present in the lipopolysaccharide extract from the reference strain for Serratia marcescens serogroup O18" -
Carbohydrate Research 215 (1991) 293-301
The lipopolysaccharide extract from the cell wall of the reference strain for Serratia marcescens serogroup O18 contained, in addition to a neutral glycan characterised previously, an acidic glycan. Acidity was contributed both by D-glucuronic acid and by 4-O-[(R)-1-carboxyethyl]-D-glucose (4-O-Lac-D-Glc). By using n.m.r. spectroscopy, methylation analysis, and chemical degradations, the repeating unit of the acidic glycan was identified as a branched hexasaccharide having the structure shown; an O-acetyl group also present was not located. The glycan is believed to define the O18 serogroup, but is probably not an integral component of the lipopolysaccharide. [formula: see text].
NCBI PubMed ID: 1794127Publication DOI: 10.1016/0008-6215(91)84028-dJournal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Chemistry, The University, Hull, Great Britain
Methods: 13C NMR, 1H NMR, ESI-MS
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13. Compound ID: 2013
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, cell wall polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_142488,IEDB_144144,IEDB_144825,IEDB_144998,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 619
Aucken HM, Wilkinson SG, Pitt TL "Re-evaluation of the serotypes of Serratia marcescens and separation into two schemes based on lipopolysaccharide (O) and capsular polysaccharide (K) antigens" -
Microbiology 144 (1998) 639-653
Chemical and serological analysis has revealed that many of the 29 O serotype reference strains of Serratia marcescens contain both neutral and acidic polysaccharides which correspond to LPS O antigens and capsular K antigens, respectively. New O and K antigen typing schemes have therefore been devised, based on the known chemical structures of the surface polysaccharides of the organism. These schemes were designed to allow the specific detection of these antigens on unknown strains using ELISAs. O antigens were detected using whole cells cultured in broth then autoclaved to remove capsular material, while K antigens were detected using formolized whole cells which had been cultured on glycerol agar to enhance capsule production. After testing with the 29 reference strains as well as 423 distinct clinical strains, it was apparent that different aspects of chemical structure were associated with different degrees of serological reactivity and the typing schemes were modified further to accommodate this. In general, the O antigen repeating unit structures were chemically simple with di- or trisaccharide backbones. Serological specificity was often provided solely by the presence or absence of an O-acetyl substituent, or a change in the linkage between two sugar residues. Five of the O serotypes in the new scheme were represented by 12 of the 29 reference strains, while three reference strains lacked O antigens altogether, resulting in the elimination of 10 of the original O types. In contrast, the K antigen repeating unit structures were more complex and chemically diverse, having at least four sugar residues. Three K types were each seen in two reference strains while 12 of the 29 reference strains were acapsular. Thus, the resulting schemes contain 19 O types and 14 K types and allow the definitive serotype identification of S. marcescens.
Lipopolysaccharide, antigen, LPS, structure, K-antigen, O-antigen, capsular polysaccharide, Serratia marcescens, Serratia, serotyping, O-serotype
NCBI PubMed ID: 9534235Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: haucken@phls.co.uk
Institutions: Laboratory of Hospital Infection, Central Public Health Laboratory, 61 Colindale Avenue, London NW9 5HT, UK, School of Chemistry, The University, Hull HU6 7RX, UK
Methods: NMR, SDS-PAGE, ELISA, chromatography, Quellung reaction, serum adsorption assays
- Article ID: 815
Holst O, Aucken HM, Seltmann G "Structural and serological characterization of the O-specific polysaccharide of the lipopolysaccharide from proposed new serotype O29 of Serratia marcescens" -
Journal of Endotoxin Research 4(3) (1997) 215-220
The structure of the repeating unit of the O-antigenic polysaccharide from the lipopolysaccharide (LPS) of Serratia marcescens strain 111 was determined by compositional and methylation analyses and NMR spectroscopy as →6)-a-D-Glcp-(1→2)-a-L-Rhap-(1→2)-a-L-Rhap-(1→2)-a-L-Rhap-(1→ (Rha, rhamnose) which represents a new O-antigenic structure in LPS of S. marcescens but is similar to the structure of the repeating unit of the O-antigen of S. marcescens 018: →6)-a-D-GlcpNAc-(1→2)-a-L-Rhap-(1→2)-a-L-Rhap-(1→2)-a-L-Rhap-(1→. (Oxiey D., Wilkinson S.G. Structure of a neutral polymer isolated from the lipopolysaccharide of the reference strain for S. marcescens serogroup 018. Carbohydrate Research 1989; 195: 111-115). Serological investigations using S. marcescens 0- and K-specific ELISA tests and immunoblotting showed that S111 reacted with anti-018 and anti-K4 sera, and that the anti-S111 serum reacted with serotype strain 018. The K4 reaction was confirmed as capsular by the Quellung reaction. After absorption with the heterologous strain, S. marcescens 018 and strain 111 were shown to be immunologically distinct, probably because of the presence of the GlcNAc residue in 018. We propose to add S111 to the O-serotype strains of S. marcescens as 029.
Lipopolysaccharide, LPS, structural, characterization, polysaccharide, serotype, O-specific, O-specific polysaccharide, serological, Serratia marcescens, Serratia
Journal NLM ID: 9433350Publisher: Maney Publishing
Correspondence: oholst@fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Laboratory of Hospital Infection, Public Health Laboratory Service, London, UK, Robert-Koch-lnstitut, Bundesinstitut fur Infektionskrankheiten und nicht ubertragbare Krankheiten, Bereich Wernigerode, Wernigerode, Germany
Methods: NMR-2D, methylation, GLC-MS
- Article ID: 4999
Hashimoto M, Satou R, Ozono M, Inagawa H, Soma GI "Characterization of the O-antigen polysaccharide derived from Pantoea agglomerans IG1 lipopolysaccharide" -
Carbohydrate Research 449 (2017) 32-36
A polysaccharide fraction was isolated from the Pantoea agglomerans IG1 lipopolysaccharide (IP-PA1), and its O-antigenic polysaccharide was characterized by chemical analyses and 1D and 2D 1H and 13C NMR spectroscopy. The polysaccharide is composed of linear tetrasaccharide repeating units, consisting of glucose and rhamnose, where 40% of one of the rhamnose residues is substituted with glucose: →2)-α-l-Rhap-(1→6)-α-d-Glcp-(1→2)-[β-d-Glcp-(1→3)]0.4-α-l-Rhap-(1→2)-α-l-Rhap-(1→.
Lipopolysaccharide, O-antigenic polysaccharide, NMR spectroscopy, Pantoea agglomerans, Wheat symbiotic bacteria
NCBI PubMed ID: 28686930Publication DOI: 10.1016/j.carres.2017.06.017Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: hassy@eng.kagoshima-u.ac.jp
Institutions: Department of Chemistry, Biotechnology, and Chemical Engineering, Kagoshima University, Kagoshima, Japan, Faculty of Medicine, Kagawa University, Miki-cho, Kita-gun, Kagawa, Japan, Research Institute for Healthy Living, Niigata University of Pharmacy and Applied Life Sciences, Akiba-ku, Niigata, Japan, Control of Innate Immunity TRA, Bio-Lab, Kagawa, Japan
Methods: gel filtration, 13C NMR, 1H NMR, methylation, GC-MS, sugar analysis, dephosphorylation, 31P NMR, acid hydrolysis
- Article ID: 5229
Vinogradov E, Sadovskaya I, Grard T, Murphy J, Mahony J, Chapot-Chartier MP, van Sinderen D "Structural studies of the cell wall polysaccharide from Lactococcus lactis UC509.9" -
Carbohydrate Research 461 (2018) 25-31
Lactococcus lactis is the most widely utilised starter bacterial species in dairy fermentations. The L. lactis cell envelope contains polysaccharides, which, among other known functions, serve as bacteriophage receptors. Our previous studies have highlighted the structural diversity of these so-called cell wall polysaccharides (CWPSs) among L. lactis strains that could account for the narrow host range of most lactococcal bacteriophages. In the present work, we studied the CWPS of L. lactis strain UC509.9, an Irish dairy starter strain that is host to the temperate and well-characterized P335-type phage Tuc2009. The UC509.9 CWPS structure was analyzed by methylation, deacetylation/deamination, Smith degradation and 2D NMR spectroscopy. The CWPS consists of a linear backbone composed of a tetrasaccharide repeat unit, partially substituted with a branched phosphorylated oligosaccharide having a common trisaccharide and three non-stoichiometric substitutions.
structure, NMR spectroscopy, Lactococcus lactis, Cell-wall polysaccharide
NCBI PubMed ID: 29573584Publication DOI: 10.1016/j.carres.2018.03.011Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca; D. van Sinderen
Institutions: School of Microbiology, University College Cork, Cork, Ireland, Micalis Institute, INRA, AgroParisTech, Université Paris-Saclay, Jouy-en-Josas, France, National Research Council, 100 Sussex Dr, Ottawa K1A0R6, Canada, Univ. Littoral Cote d'Opale, Convention ANSES, EA 7394, ICV Charles Violette, Univ. Lille, Univ. Artois, INRA, ISA F-62321, Boulogne-sur-mer, France
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, deacylation, acid hydrolysis, anion-exchange chromatography, Smith degradation, deamination, HPLC, GPC
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14. Compound ID: 2051
|
a-L-Rhap-(1-4)-a-D-GalpA-(1-2)-+
|
-2)-a-L-Rhap-(1-3)-b-D-Galp-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_133754,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_144825,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 657
Gray JSS, Yun Yang B, Montgomery R "Extracellular polysaccharide of Erwinia chrysanthemi A350 and ribotyping of Erwinia chrysanthemi spp." -
Carbohydrate Research 324(4) (2000) 255-267
Erwinia chrysanthemi spp. are gram-negative bacterial phytopathogens causing soft rots in a number of plants. The structure of the extracellular polysaccharide (EPS) produced by the E. chrysanthemi strain A350, which is a lacZ- mutant of the wild type strain 3937, pathogenic to Saintpaulia, has been determined using a combination of chemical and physical techniques including methylation analysis, low-pressure gel-filtration and anion-exchange chromatography, high-pH anion-exchange chromatography, partial acid hydrolysis, mass spectrometry and 1- and 2D NMR spectroscopy. In contrast to the structures of the EPS reported for other strains of E. chrysanthemi, the EPS from strain A350 contains D-GalA, together with L-Rhap and D-Galp in a 1:4:1 ratio. Evidence is presented for the following hexasaccharide repeat unit: [structure: see text] All the Erwinia chrysanthemi spp. studied to date have been analyzed by ribotyping and collated into families, which are consistent with the related structures of their EPS.
Erwinia, structure, polysaccharide, extracellular polysaccharide, extracellular, Erwinia chrysanthemi, ribotyping, Saintpaulia
NCBI PubMed ID: 10744334Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rex-montgomery@uiowa.edu
Institutions: Department of Biochemistry, College of Medicine, University of Iowa, Iowa City 52242, USA.
Methods: NMR-2D, methylation, partial acid hydrolysis, NMR, anion-exchange chromatography, MS
- Article ID: 1292
Yang BY, Brand JM, Gray JSS, Montgomery R "Extracellular polysaccharides of modified strains of Erwinia spp" -
Carbohydrate Research 333(4) (2001) 295-302
The structure of the extracellular polysaccharide (EPS) produced by Erwinia chrysanthemi strain A2148 has been determined using low pressure size-exclusion and anion-exchange chromatographies, high pH anion-exchange chromatography, glycosyl-linkage analysis, and 1D 1H NMR spectroscopy. The polysaccharide is structurally similar, if not identical, to the EPS produced by E. chrysanthemi strain A350. A streptomycin-resistant strain of E. chrysanthemi Ech6 (Ech6S(+)) has been generated and has an elevated production of EPS, as does a streptomycin-resistant strain (Ech9Sm6) of E. chrysanthemi Ech9. These modified E. chrysanthemi spp. have been ribotyped and found to be closely related to their parent strains
structure, extracellular polysaccharide, Erwinia spp., ribotyping, Streptomycin
NCBI PubMed ID: 11454336Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rex-montgomery@uiowa.edu
Institutions: Department of Biochemistry, College of Medicine, University of Iowa, 52242, Iowa City, IA, USA
Methods: methylation, NMR, HPAEC, Li/ethylenediamine degradation
- 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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15. Compound ID: 2514
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a-D-Fucp3NAc-(1-2)-+
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-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, LPS
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_144825,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- 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: 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: 1315
Zdorovenko EL, Zatonsky GV, Kocharova NA, Shashkov AS, Knirel YA, Ovod V "Structure of the O-polysaccharide of Pseudomonas syringae pv. delphinii NCPPB 1879T having side chains of 3-acetamido-3,6-dideoxy-D-galactose residues" -
Biochemistry (Moscow) 67(5) (2002) 558-565
The O-polysaccharide (OPS) was obtained from the lipopolysaccharide of Pseudomonas syringae pv. delphinii NCPPB 1879(T) and studied by sugar and methylation analyses, Smith degradation, and (1)H- and (13)C-NMR spectroscopy. The OPS was found to contain residues of L-rhamnose (L-Rha) and 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc), and the following structure of the major (n = 2) and minor (n = 3) heptasaccharide repeating units of the OPS was established: [carbohydrate structure: see text]. The OPS is distinguished by the presence of oligosaccharide side chains consisting of three D-Fuc3NAc residues that are connected to each other by the (α 1→2)-linkage. The OPS is characterized by a structural heterogeneity due to a different position of substitution of one of the four L-rhamnose residues in the main chain of the repeating unit as well as to the presence of oligosaccharide units with an incomplete side chain
Lipopolysaccharide, O-specific polysaccharide, 6-dideoxy-D-galactose, 3-Acetamido-3, Pseudomonas syringae
NCBI PubMed ID: 12059776Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Medical Technology, University of Tampere, 33101 Tampere, P.O. Box 607, Finland, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia 2Institute of Medical Technology, University of Tampere, 33101 Tampere, P.O. Box 607, Finland
Methods: NMR-2D, methylation, NMR, Smith degradation
- Article ID: 1452
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- Article ID: 2610
Das S, Ramm M, Kochanowski H, Basu S "Structural studies of the side chain of outer membrane lipopolysaccharide from Pseudomonas syringae pv. coriandricola W-43" -
Journal of Bacteriology 176 (1994) 6550-6556
Journal NLM ID: 2985120RPublisher: American Society for Microbiology
- 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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