Found 266 structures.
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1. Compound ID: 324
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a-L-Rhap-(1-3)-a-D-Fucp-(1-2)-+
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-4)-a-L-Rhap-(1-3)-b-D-Manp2Ac-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115015,IEDB_136105,IEDB_137485,IEDB_142489,IEDB_144983,IEDB_149135,IEDB_152206,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 89
Galbraith L, Wilkinson SG "Structural studies on the O-specific side-chain of lipopolysaccharide from Burkholderia gladioli pv. gladioli strain NCPPB 1891" -
Carbohydrate Research 303 (1997) 245-249
A polymeric fraction (the O-antigenic side-chain) has been isolated from the lipopolysaccharide of Burkholderia gladioli pv. gladioli strain NCPPB 1891 after mild acid hydrolysis. The components of the polymer and their molar proportions were L-Rha (1), D-Gal (1), D-Man (1), and O-acetyl (1). By means of chemical degradations and NMR studies, the repeating unit of the polymer was shown to be a linear trisaccharide of the structure shown. [formula: see text]
Lipopolysaccharide, O-antigen, Burkholderia gladioli
NCBI PubMed ID: 9352638Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: S.G.Wilkison@chem.hull.ac.uk
Institutions: School of Chemistry, University of Hull, UK
Methods: NMR-2D, methylation, NMR, sugar analysis
- 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: 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: 2191
Vinogradov EV, Daeva ED, Shashkov AS, Knirel YA, Zdorovenko GM, Yakovleva LM, Gubanova NY, Solyanik LP "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide chain of Pseudomonas gladioli pv. alliicola 8494 (serogroup X) lipopolysaccharide" -
Carbohydrate Research 212 (1991) 313-320
No abstract available
NCBI PubMed ID: 1720349Publication DOI: 10.1016/0008-6215(91)84072-mJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, GLC, Smith degradation, de-O-acetylation
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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2. Compound ID: 431
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b-D-GlcpNAc-(1-2)-+
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-3)-b-L-Rhap2Ac-(1-4)-a-L-Rhap-(1-3)-a-D-Fucp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115015,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_149135,IEDB_151531,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 158
Veremeychenko SN, Zdorovenko GM "Characterization of the lipopolysaccharide from the Pseudomonas fluorescens strain IMV 472 (biovar I)" -
Mikrobiologiia = Microbiology [Russian] 65(3) (1996) 318-325
Lipopolysaccharide was isolated from dry biomass of the Pseudomonas fluorescens strain IMV 472 (biovar I) by the Westphal procedure and purified by ultracentrifugation. Fractions of the structural components of the lipopolysaccharide macromolecule-lipid A, the core oligosaccharide, and the O-chain-were isolated and characterized. 3-Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, hexadecenoic, octadecenoic, and hexadecanoic acids were identified as the main fatty acids of lipid A. The hydrophilic moiety of lipid A was found to include glucosamine, phosphoethanolamine, and phosphate. Glucose, galactose, rhamnose, glucosamine, galactosamine, alanine, phosphoethanolamine, and 2-keto-3-deoxyoctulosonic were identified in the core region of lipid A. The O-specific polysaccharide chain consisted of a repeating tetrasaccharide fragment that included two L-rhamnose residues, a D-fucose residue, and an N-acetyl-D-glucosamine residue as a side substituent. Double immunodiffusion in agar and the lipopolysaccharide precipitation reaction revealed no serological interrelation between strain IMV 472 and P. fluorescens strains studied previously.
Lipopolysaccharide, LPS, strain, characterization, Pseudomonas, fatty acid, O-chain, biovar, Pseudomonas fluorescens
NCBI PubMed ID: 8992240Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine
Methods: 13C NMR, 1H NMR, NMR-2D, NMR
- Article ID: 2306
Knirel YA, Veremeychenko SN, Zdorovenko GM, Shashkov AS, Paramonov NA, Zakharova IY, Kochetkov NK "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide of Pseudomonas fluorescens biovar A strain IMV 472" -
Carbohydrate Research 259 (1994) 147-151
NCBI PubMed ID: 7518743Journal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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3. Compound ID: 447
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b-D-GlcpNAc-(1-2)-+
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-3)-b-L-Rhap-(1-4)-a-L-Rhap-(1-3)-a-D-Fucp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115015,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_149135,IEDB_151531,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 158
Veremeychenko SN, Zdorovenko GM "Characterization of the lipopolysaccharide from the Pseudomonas fluorescens strain IMV 472 (biovar I)" -
Mikrobiologiia = Microbiology [Russian] 65(3) (1996) 318-325
Lipopolysaccharide was isolated from dry biomass of the Pseudomonas fluorescens strain IMV 472 (biovar I) by the Westphal procedure and purified by ultracentrifugation. Fractions of the structural components of the lipopolysaccharide macromolecule-lipid A, the core oligosaccharide, and the O-chain-were isolated and characterized. 3-Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, hexadecenoic, octadecenoic, and hexadecanoic acids were identified as the main fatty acids of lipid A. The hydrophilic moiety of lipid A was found to include glucosamine, phosphoethanolamine, and phosphate. Glucose, galactose, rhamnose, glucosamine, galactosamine, alanine, phosphoethanolamine, and 2-keto-3-deoxyoctulosonic were identified in the core region of lipid A. The O-specific polysaccharide chain consisted of a repeating tetrasaccharide fragment that included two L-rhamnose residues, a D-fucose residue, and an N-acetyl-D-glucosamine residue as a side substituent. Double immunodiffusion in agar and the lipopolysaccharide precipitation reaction revealed no serological interrelation between strain IMV 472 and P. fluorescens strains studied previously.
Lipopolysaccharide, LPS, strain, characterization, Pseudomonas, fatty acid, O-chain, biovar, Pseudomonas fluorescens
NCBI PubMed ID: 8992240Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine
Methods: 13C NMR, 1H NMR, NMR-2D, NMR
- Article ID: 1777
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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4. Compound ID: 696
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b-L-Arap4N-(1--P--6)--a-D-GlcpN-(1-4)-a-Kdop-(2-4)-+
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b-D-GlcpNAc-(1-4)-+ a-D-6dTalp2Ac3Me-(1-3)-+ a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-a-D-Galp-(1-2)-+ |
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a-D-GlcpNAc-(1-3)-a-D-Fucp-(1-2)-b-D-GlcpA-(1-4)-a-D-Fucp-(1-3)-a-D-GalpNAc-(1-4)-b-D-ManpNAc-(1-4)-a-D-Galp-(1-3)-b-D-GalpNAc-(1-3)-a-D-Glcp-(1-3)-a-D-Manp-(1-6)-a-D-Manp-(1-4)-a-D-Manp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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a-Kdop-(2-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_130648,IEDB_130650,IEDB_130659,IEDB_130701,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140116,IEDB_140630,IEDB_141584,IEDB_141793,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144983,IEDB_144990,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_167071,IEDB_190606,IEDB_232584,IEDB_423153,IEDB_885813,IEDB_885822,IEDB_983930,IEDB_983931,SB_192,SB_198,SB_44,SB_67,SB_7,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 186
Vinogradov E, Petersen BO, Sadovskaya I, Jabbouri S, Duus J, Helander IM "Structure of the exceptionally large nonrepetitive carbohydrate backbone of the lipopolysaccharide of Pectinatus frisingensis strain VTT E-82164" -
European Journal of Biochemistry 270(14) (2003) 3036-3046
The structures of the oligosaccharides obtained after acetic acid hydrolysis and alkaline deacylation of the rough-type lipopolysaccharide (LPS) from Pectinatus frisingensis strain VTT E-82164 were analysed using NMR spectroscopy, MS and chemical methods. The LPS contains two major structural variants, differing by a decasaccharide fragment, and some minor variants lacking the terminal glucose residue. The largest structure of the carbohydrate backbone of the LPS that could be deduced from experimental results consists of 25 monosaccharides (including the previously found Arap4NP residue in lipid A) arranged in a well-defined nonrepetitive structure: We presume that the shorter variant with R1 = H represents the core-lipid A part of the LPS, and the additional fragment is present instead of the O-specific polysaccharide. Structures of this type have not been previously described. Analysis of the deacylation products obtained from the LPS of the smooth strain, VTT E-79100T, showed that it contains a very similar core but with one different glycosidic linkage.
Lipopolysaccharide, structure, core, strain, carbohydrate, lipid A, backbone, Pectinatus
NCBI PubMed ID: 12846837Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Laboratoire de Recherche sur les Biomateriaux et Biotechnologies, Universite de Littoral-Cote d'Opale, Bassin Napoleon BP 120, Boulogne-sur-mer, France, Department of Applied Chemistry and Microbiology, Division of Microbiology, University of Helsinki, Finland
Methods: NMR-2D, NMR, chemical methods, MS
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5. Compound ID: 699
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a-D-GlcpN-(1-4)-a-Kdop-(2-4)-+
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b-D-GlcpN-(1-4)-+ a-D-6dTalp3Me-(1-3)-+ a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-a-D-Galp-(1-2)-+ |
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a-D-GlcpN-(1-3)-a-D-Fucp-(1-2)-b-D-GlcpA-(1-4)-a-D-Fucp-(1-3)-a-D-GalpN-(1-4)-b-D-ManpN-(1-4)-a-D-Galp-(1-3)-b-D-GalpN-(1-3)-a-D-Glcp-(1-3)-a-D-Manp-(1-6)-a-D-Manp-(1-4)-a-D-Manp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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a-Kdop-(2-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_130650,IEDB_130659,IEDB_130701,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_140116,IEDB_140630,IEDB_141793,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_190606,IEDB_232584,IEDB_423153,IEDB_983930,IEDB_983931,SB_192,SB_198,SB_44,SB_67,SB_7,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 186
Vinogradov E, Petersen BO, Sadovskaya I, Jabbouri S, Duus J, Helander IM "Structure of the exceptionally large nonrepetitive carbohydrate backbone of the lipopolysaccharide of Pectinatus frisingensis strain VTT E-82164" -
European Journal of Biochemistry 270(14) (2003) 3036-3046
The structures of the oligosaccharides obtained after acetic acid hydrolysis and alkaline deacylation of the rough-type lipopolysaccharide (LPS) from Pectinatus frisingensis strain VTT E-82164 were analysed using NMR spectroscopy, MS and chemical methods. The LPS contains two major structural variants, differing by a decasaccharide fragment, and some minor variants lacking the terminal glucose residue. The largest structure of the carbohydrate backbone of the LPS that could be deduced from experimental results consists of 25 monosaccharides (including the previously found Arap4NP residue in lipid A) arranged in a well-defined nonrepetitive structure: We presume that the shorter variant with R1 = H represents the core-lipid A part of the LPS, and the additional fragment is present instead of the O-specific polysaccharide. Structures of this type have not been previously described. Analysis of the deacylation products obtained from the LPS of the smooth strain, VTT E-79100T, showed that it contains a very similar core but with one different glycosidic linkage.
Lipopolysaccharide, structure, core, strain, carbohydrate, lipid A, backbone, Pectinatus
NCBI PubMed ID: 12846837Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Laboratoire de Recherche sur les Biomateriaux et Biotechnologies, Universite de Littoral-Cote d'Opale, Bassin Napoleon BP 120, Boulogne-sur-mer, France, Department of Applied Chemistry and Microbiology, Division of Microbiology, University of Helsinki, Finland
Methods: NMR-2D, NMR, chemical methods, MS
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6. Compound ID: 700
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a-D-GlcpN-(1-4)-a-Kdop-(2-4)-+
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b-D-GlcpN-(1-4)-+ a-D-6dTalp3Me-(1-3)-+ a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-a-D-Galp-(1-2)-+ |
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a-D-GlcpN-(1-3)-a-D-Fucp-(1-2)-a-D-GlcpA-(1-4)-a-D-Fucp-(1-3)-a-D-GalpN-(1-4)-b-D-ManpN-(1-4)-a-D-Galp-(1-3)-b-D-GalpN-(1-3)-a-D-Glcp-(1-3)-a-D-Manp-(1-6)-a-D-Manp-(1-4)-a-D-Manp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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a-Kdop-(2-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_130650,IEDB_130659,IEDB_130701,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_140116,IEDB_140630,IEDB_141793,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_190606,IEDB_232584,IEDB_983930,IEDB_983931,SB_192,SB_198,SB_44,SB_67,SB_7,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 186
Vinogradov E, Petersen BO, Sadovskaya I, Jabbouri S, Duus J, Helander IM "Structure of the exceptionally large nonrepetitive carbohydrate backbone of the lipopolysaccharide of Pectinatus frisingensis strain VTT E-82164" -
European Journal of Biochemistry 270(14) (2003) 3036-3046
The structures of the oligosaccharides obtained after acetic acid hydrolysis and alkaline deacylation of the rough-type lipopolysaccharide (LPS) from Pectinatus frisingensis strain VTT E-82164 were analysed using NMR spectroscopy, MS and chemical methods. The LPS contains two major structural variants, differing by a decasaccharide fragment, and some minor variants lacking the terminal glucose residue. The largest structure of the carbohydrate backbone of the LPS that could be deduced from experimental results consists of 25 monosaccharides (including the previously found Arap4NP residue in lipid A) arranged in a well-defined nonrepetitive structure: We presume that the shorter variant with R1 = H represents the core-lipid A part of the LPS, and the additional fragment is present instead of the O-specific polysaccharide. Structures of this type have not been previously described. Analysis of the deacylation products obtained from the LPS of the smooth strain, VTT E-79100T, showed that it contains a very similar core but with one different glycosidic linkage.
Lipopolysaccharide, structure, core, strain, carbohydrate, lipid A, backbone, Pectinatus
NCBI PubMed ID: 12846837Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Laboratoire de Recherche sur les Biomateriaux et Biotechnologies, Universite de Littoral-Cote d'Opale, Bassin Napoleon BP 120, Boulogne-sur-mer, France, Department of Applied Chemistry and Microbiology, Division of Microbiology, University of Helsinki, Finland
Methods: NMR-2D, NMR, chemical methods, MS
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7. Compound ID: 702
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a-6dTalp3Me-(1-3)-+
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a-D-Fucp-(1-2)-b-D-GlcpA-(1-4)-a-D-Fucp-(1-3)-D-2,5anhTal-ol |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_140630,IEDB_142489,IEDB_149135,IEDB_423153,SB_86
The structure is contained in the following publication(s):
- Article ID: 186
Vinogradov E, Petersen BO, Sadovskaya I, Jabbouri S, Duus J, Helander IM "Structure of the exceptionally large nonrepetitive carbohydrate backbone of the lipopolysaccharide of Pectinatus frisingensis strain VTT E-82164" -
European Journal of Biochemistry 270(14) (2003) 3036-3046
The structures of the oligosaccharides obtained after acetic acid hydrolysis and alkaline deacylation of the rough-type lipopolysaccharide (LPS) from Pectinatus frisingensis strain VTT E-82164 were analysed using NMR spectroscopy, MS and chemical methods. The LPS contains two major structural variants, differing by a decasaccharide fragment, and some minor variants lacking the terminal glucose residue. The largest structure of the carbohydrate backbone of the LPS that could be deduced from experimental results consists of 25 monosaccharides (including the previously found Arap4NP residue in lipid A) arranged in a well-defined nonrepetitive structure: We presume that the shorter variant with R1 = H represents the core-lipid A part of the LPS, and the additional fragment is present instead of the O-specific polysaccharide. Structures of this type have not been previously described. Analysis of the deacylation products obtained from the LPS of the smooth strain, VTT E-79100T, showed that it contains a very similar core but with one different glycosidic linkage.
Lipopolysaccharide, structure, core, strain, carbohydrate, lipid A, backbone, Pectinatus
NCBI PubMed ID: 12846837Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Laboratoire de Recherche sur les Biomateriaux et Biotechnologies, Universite de Littoral-Cote d'Opale, Bassin Napoleon BP 120, Boulogne-sur-mer, France, Department of Applied Chemistry and Microbiology, Division of Microbiology, University of Helsinki, Finland
Methods: NMR-2D, NMR, chemical methods, MS
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8. Compound ID: 704
|
b-D-GlcpNAc-(1-4)-+ a-D-6dTalp3Me-(1-3)-+ a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-a-D-Galp-(1-2)-+
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a-D-GlcpNAc-(1-3)-a-D-Fucp-(1-2)-b-D-GlcpA-(1-4)-a-D-Fucp-(1-3)-a-D-GalpNAc-(1-4)-b-D-ManpNAc-(1-4)-a-D-Galp-(1-3)-b-D-GalpNAc-(1-3)-a-D-Glcp-(1-3)-a-D-Manp-(1-6)-a-D-Manp-(1-4)-a-D-Manp-(1-5)-Kdo-ol |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_130648,IEDB_130701,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140116,IEDB_140630,IEDB_141584,IEDB_141793,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144983,IEDB_144990,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_167071,IEDB_190606,IEDB_232584,IEDB_423153,IEDB_885813,IEDB_885822,IEDB_983930,IEDB_983931,SB_192,SB_198,SB_44,SB_67,SB_7,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 186
Vinogradov E, Petersen BO, Sadovskaya I, Jabbouri S, Duus J, Helander IM "Structure of the exceptionally large nonrepetitive carbohydrate backbone of the lipopolysaccharide of Pectinatus frisingensis strain VTT E-82164" -
European Journal of Biochemistry 270(14) (2003) 3036-3046
The structures of the oligosaccharides obtained after acetic acid hydrolysis and alkaline deacylation of the rough-type lipopolysaccharide (LPS) from Pectinatus frisingensis strain VTT E-82164 were analysed using NMR spectroscopy, MS and chemical methods. The LPS contains two major structural variants, differing by a decasaccharide fragment, and some minor variants lacking the terminal glucose residue. The largest structure of the carbohydrate backbone of the LPS that could be deduced from experimental results consists of 25 monosaccharides (including the previously found Arap4NP residue in lipid A) arranged in a well-defined nonrepetitive structure: We presume that the shorter variant with R1 = H represents the core-lipid A part of the LPS, and the additional fragment is present instead of the O-specific polysaccharide. Structures of this type have not been previously described. Analysis of the deacylation products obtained from the LPS of the smooth strain, VTT E-79100T, showed that it contains a very similar core but with one different glycosidic linkage.
Lipopolysaccharide, structure, core, strain, carbohydrate, lipid A, backbone, Pectinatus
NCBI PubMed ID: 12846837Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Laboratoire de Recherche sur les Biomateriaux et Biotechnologies, Universite de Littoral-Cote d'Opale, Bassin Napoleon BP 120, Boulogne-sur-mer, France, Department of Applied Chemistry and Microbiology, Division of Microbiology, University of Helsinki, Finland
Methods: NMR-2D, NMR, chemical methods, MS
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9. Compound ID: 705
|
b-D-GlcpNAc-(1-4)-+ a-D-6dTalp2Ac3Me-(1-3)-+ a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-a-D-Galp-(1-2)-+
| | |
a-D-GlcpNAc-(1-3)-a-D-Fucp-(1-2)-b-D-GlcpA-(1-4)-a-D-Fucp-(1-3)-a-D-GalpNAc-(1-4)-b-D-ManpNAc-(1-4)-a-D-Galp-(1-3)-b-D-GalpNAc-(1-3)-a-D-Glcp-(1-3)-a-D-Manp-(1-6)-a-D-Manp-(1-4)-a-D-Manp-(1-5)-Kdo |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_130648,IEDB_130650,IEDB_130701,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140116,IEDB_140630,IEDB_141584,IEDB_141793,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144983,IEDB_144990,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_167071,IEDB_190606,IEDB_232584,IEDB_423153,IEDB_885813,IEDB_885822,IEDB_983930,IEDB_983931,SB_192,SB_198,SB_44,SB_67,SB_7,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 186
Vinogradov E, Petersen BO, Sadovskaya I, Jabbouri S, Duus J, Helander IM "Structure of the exceptionally large nonrepetitive carbohydrate backbone of the lipopolysaccharide of Pectinatus frisingensis strain VTT E-82164" -
European Journal of Biochemistry 270(14) (2003) 3036-3046
The structures of the oligosaccharides obtained after acetic acid hydrolysis and alkaline deacylation of the rough-type lipopolysaccharide (LPS) from Pectinatus frisingensis strain VTT E-82164 were analysed using NMR spectroscopy, MS and chemical methods. The LPS contains two major structural variants, differing by a decasaccharide fragment, and some minor variants lacking the terminal glucose residue. The largest structure of the carbohydrate backbone of the LPS that could be deduced from experimental results consists of 25 monosaccharides (including the previously found Arap4NP residue in lipid A) arranged in a well-defined nonrepetitive structure: We presume that the shorter variant with R1 = H represents the core-lipid A part of the LPS, and the additional fragment is present instead of the O-specific polysaccharide. Structures of this type have not been previously described. Analysis of the deacylation products obtained from the LPS of the smooth strain, VTT E-79100T, showed that it contains a very similar core but with one different glycosidic linkage.
Lipopolysaccharide, structure, core, strain, carbohydrate, lipid A, backbone, Pectinatus
NCBI PubMed ID: 12846837Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Laboratoire de Recherche sur les Biomateriaux et Biotechnologies, Universite de Littoral-Cote d'Opale, Bassin Napoleon BP 120, Boulogne-sur-mer, France, Department of Applied Chemistry and Microbiology, Division of Microbiology, University of Helsinki, Finland
Methods: NMR-2D, NMR, chemical methods, MS
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10. Compound ID: 821
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115015,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_149135,IEDB_151531,SB_86
The structure is contained in the following publication(s):
- Article ID: 223
Winn AM, Miles CT, Wilkinson SG "Structure of the O3 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia" -
Carbohydrate Research 282 (1996) 149-156
The O atnigen isolated from the lipopolysaccharide of a strain of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia serogroup O3 was found to contain 4-acetamido-4,6,-dideoxy-D-galactose, D-fucose, and N-acetyo-D-glucosamine. By means of chemical degradations and NMR spectroscopy the repeating unit of the O-specific polymer was determined to by a branched trisaccharide repeating-unit of the structure shown. [see formula in text]
Lipopolysaccharide, O-antigen, Stenotrophomonsa meltophilia
NCBI PubMed ID: 8721742Journal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Chemistry, University of Hull, Hull HU6 7RX, UK
Methods: NMR, chemical methods
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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11. Compound ID: 1173
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_140630,IEDB_142489,IEDB_149135,SB_86
The structure is contained in the following publication(s):
- Article ID: 359
Ridley BL, Jeyaretnam BS, Carlson RW "The type and yield of lipopolysaccharide from symbiotically deficient Rhizobium lipopolysaccharide mutants vary depending on the extraction method" -
Glycobiology 10(10) (2000) 1013-1023
At least 18 lipopolysaccharide (LPS) extraction methods are available, and no single method is universally applicable. Here, the LPSs from four R.etli, one R.leguminosarum bv. trifolii mutant, 24AR, and the R.etli parent strain, CE3, were isolated by hot phenol/water (phi;/W), and phenol/EDTA/triethylamine (phi/EDTA/TEA) extraction. The LPS in various preparations was quantified, analyzed by deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE), and by immunoblotting. These rhizobia normally have two prominent LPS forms: LPS I, which has O-polysaccharide, and LPS II, which has none. The LPS forms obtained depend on the method of extraction and vary depending on the mutant that is extracted. Both methods extract LPS I and LPS II from CE3. The phi/EDTA/TEA, but not the phi/W, method extracts LPS I from mutants CE358 and CE359. Conversely, the phi;/W but not the phi;/EDTA/TEA method extracts CE359 LPS V, an LPS form with a truncated O-polysaccharide. phi/EDTA/TEA extraction of mutant CE406 gives good yields of LPS I and II, while phi/W extraction gives very small amounts of LPS I. The LPS yield from all the strains using phi/EDTA/TEA extraction is fairly consistent (3-fold range), while the yields from phi/W extraction are highly variable (850-fold range). The phi/EDTA/TEA method extracts LPS I and LPS II from mutant 24AR, but the phi/W method partitions LPS II exclusively into the phenol phase, making its recovery difficult. Overall, phi/EDTA/TEA extraction yields more forms of LPS from the mutants and provides a simpler, faster, and less hazardous alternative to phi/W extraction. Nevertheless, it is concluded that careful analysis of any LPS mutant requires the use of more than one extraction method.
Lipopolysaccharide, mutants, Rhizobium elti, Rhizobium leguminosarum bv. trifolii, extraction method
NCBI PubMed ID: 11030747Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Complex Carbohydrate Research Center, University of Georgia, 220 Reverbend Road, Athens, GA 30602, USA
Methods: DOC-PAGE, immunoblotting, extraction
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12. Compound ID: 1174
|
a-D-GalpA-(1-5)-+
|
a-D-GalpA-(1-4)-a-Kdop-(2-4)-+
|
a-D-GalpA-(1-4)-+ |
| |
a-D-Fucp-(1-3)-a-D-Manp-(1-3)-a-D-QuipNAc-(1-4)-a-Kdop-(2-6)-a-D-Galp-(1-6)-a-D-Manp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115015,IEDB_130650,IEDB_130659,IEDB_130701,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142489,IEDB_144983,IEDB_149135,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_983930,SB_44,SB_67,SB_7,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 359
Ridley BL, Jeyaretnam BS, Carlson RW "The type and yield of lipopolysaccharide from symbiotically deficient Rhizobium lipopolysaccharide mutants vary depending on the extraction method" -
Glycobiology 10(10) (2000) 1013-1023
At least 18 lipopolysaccharide (LPS) extraction methods are available, and no single method is universally applicable. Here, the LPSs from four R.etli, one R.leguminosarum bv. trifolii mutant, 24AR, and the R.etli parent strain, CE3, were isolated by hot phenol/water (phi;/W), and phenol/EDTA/triethylamine (phi/EDTA/TEA) extraction. The LPS in various preparations was quantified, analyzed by deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE), and by immunoblotting. These rhizobia normally have two prominent LPS forms: LPS I, which has O-polysaccharide, and LPS II, which has none. The LPS forms obtained depend on the method of extraction and vary depending on the mutant that is extracted. Both methods extract LPS I and LPS II from CE3. The phi/EDTA/TEA, but not the phi/W, method extracts LPS I from mutants CE358 and CE359. Conversely, the phi;/W but not the phi;/EDTA/TEA method extracts CE359 LPS V, an LPS form with a truncated O-polysaccharide. phi/EDTA/TEA extraction of mutant CE406 gives good yields of LPS I and II, while phi/W extraction gives very small amounts of LPS I. The LPS yield from all the strains using phi/EDTA/TEA extraction is fairly consistent (3-fold range), while the yields from phi/W extraction are highly variable (850-fold range). The phi/EDTA/TEA method extracts LPS I and LPS II from mutant 24AR, but the phi/W method partitions LPS II exclusively into the phenol phase, making its recovery difficult. Overall, phi/EDTA/TEA extraction yields more forms of LPS from the mutants and provides a simpler, faster, and less hazardous alternative to phi/W extraction. Nevertheless, it is concluded that careful analysis of any LPS mutant requires the use of more than one extraction method.
Lipopolysaccharide, mutants, Rhizobium elti, Rhizobium leguminosarum bv. trifolii, extraction method
NCBI PubMed ID: 11030747Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Complex Carbohydrate Research Center, University of Georgia, 220 Reverbend Road, Athens, GA 30602, USA
Methods: DOC-PAGE, immunoblotting, extraction
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13. Compound ID: 1241
|
Pyr-(2-6:2-4)-b-D-Galp-(1-4)-b-D-GlcpA-(1-3)-b-D-Galp-(1-4)-+
|
-3)-b-D-Fucp-(1-4)-a-D-Fucp2Ac-(1-3)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: colanic acid
Compound class: EPS
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_136044,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_190606,IEDB_423153,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 384
Stevenson G, Andrianopoulos K, Hobbs M, Reeves PR "Organization of the Escherichia coli K-12 gene cluster responsible for production of the extracellular polysaccharide colanic acid" -
Journal of Bacteriology 178(16) (1996) 4885-4893
Colanic acid (CA) is an extracellular polysaccharide produced by most Escherichia coli strains as well as by other species of the family Enterobacteriaceae. We have determined the sequence of a 23-kb segment of the E. coli K-12 chromosome which includes the cluster of genes necessary for production of CA. The CA cluster comprises 19 genes. Two other sequenced genes (orf1.3 and galF), which are situated between the CA cluster and the O-antigen cluster, were shown to be unnecessary for CA production. The CA cluster includes genes for synthesis of GDP-L-fucose, one of the precursors of CA, and the gene for one of the enzymes in this pathway (GDP-D-mannose 4,6-dehydratase) was identified by biochemical assay. Six of the inferred proteins show sequence similarity to glycosyl transferases, and two others have sequence similarity to acetyl transferases. Another gene (wzx) is predicted to encode a protein with multiple transmembrane segments and may function in export of the CA repeat unit from the cytoplasm into the periplasm in a process analogous to O-unit export. The first three genes of the cluster are predicted to encode an outer membrane lipoprotein, a phosphatase, and an inner membrane protein with an ATP-binding domain. Since homologs of these genes are found in other extracellular polysaccharide gene clusters, they may have a common function, such as export of polysaccharide from the cell.
gene, polysaccharide, Escherichia, Escherichia coli, acid, cluster, gene cluster, extracellular polysaccharide, production, extracellular, organization, colanic acid
NCBI PubMed ID: 8759852Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.su.oz.au
Institutions: Department of Microbiology, University of Sydney, New South Wales 2006, Australia
Methods: genetic methods
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14. Compound ID: 1282
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115015,IEDB_136095,IEDB_137472,IEDB_142489,IEDB_149135,IEDB_190606,SB_86
The structure is contained in the following publication(s):
- Article ID: 404
Vinion-Dubiel AD, Goldberg JB "Lipopolysaccharide of Burkholderia cepacia complex" -
Journal of Endotoxin Research 9(4) (2003) 201-213
Burkholderia cepacia complex (Bcc) is a group of phenotypically similar, genetically distinct bacteria that are beneficial to the environment but can also cause severe human infections. Bcc are being exploited for use as bioremediation agents and as a way to combat agricultural plant diseases. However, Bcc can cause lung infections in patients with chronic granulomatous disease or cystic fibrosis often resulting in mortality of these patients. Since it is unclear what bacterial components are necessary for causing human infections, studies of Bcc have focused on identifying putative virulence factors. As in other Gram-negative bacteria, the lipopolysaccharide (LPS) of Bcc induces a strong immune response that can contribute to host cell damage. The unusual structure of Bcc LPS lowers the anionic charge of the Bcc cell surface, which inhibits the binding and subsequent effects of cationic antibiotics. These distinguishing features include the substitution of a Ko for a Kdo residue in the inner core oligosaccharide and Ara4N residues bound to phosphates of the lipid A backbone. The structures of O antigen subunits and the consequent serotypes will also be discussed, with particular reference to the O antigen biosynthetic loci of two Bcc strains.
Lipopolysaccharide, structure, Burkholderia, Burkholderia cepacia, O-antigen, complex, endotoxin, Re
NCBI PubMed ID: 12935351Publication DOI: 10.1177/09680519030090040101Journal NLM ID: 9433350Publisher: Maney Publishing
Institutions: Department of Microbiology, University of Virginia Health Sciences Center, Charlottesville, VA 22908-0734, USA
- 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: 1862
Knirel YA, Shashkov AS, Soldatkina MA, Paramonov NA, Zakharova IY "Antigenic polysaccharides of bacteria. 32. Structure of O-specific polysaccharide chains of lipopolysaccharides from Pseudomonas cepacia serotypes B and E containing D-fucose" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14(9) (1988) 1208-1213
On the basis of acid hydrolysis, methylation, 1H and 13C NMR analysis, and calculation of specific optical rotation, the following structures were established for O-specific polysaccharides of Pseudomonas cepacia serotypes B and E: →3)-β-D-Galf-(1→3)-α-D-Fucp-(1→ serotype B →3)-β-D-GlcpNAc-(1→3)-α-D-Fucp-(1→ serotype E A characteristic feature of the polysaccharides is the presence of D-fucose, rather rare for bacterial antigens.
Journal NLM ID: 7804941WWW link: http://europepmc.org/abstract/med/2464349Publisher: 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: 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: 5143
Cloutier M, Muru K, Ravicoularamin G, Gauthier C "Polysaccharides from Burkholderia species as targets for vaccine development, immunomodulation and chemical synthesis" -
Natural Product Reports 35(12) (2018) 1251-1293
Burkholderia species are a vast group of human pathogenic, phytopathogenic, and plant- or environment-associated bacteria. B. pseudomallei, B. mallei, and B. cepacia complex are the causative agents of melioidosis, glanders, and cystic fibrosis-related infections, respectively, which are fatal diseases in humans and animals. Due to their high resistance to antibiotics, high mortality rates, and increased infectivity via the respiratory tract, B. pseudomallei and B. mallei have been listed as potential bioterrorism agents by the Centers for Disease Control and Prevention. Burkholderia species are able to produce a large network of surface-exposed polysaccharides, i.e., lipopolysaccharides, capsular polysaccharides, and exopolysaccharides, which are virulence factors, immunomodulators, major biofilm components, and protective antigens, and have crucial implications in the pathogenicity of Burkholderia-associated diseases. This review provides a comprehensive and up-to-date account regarding the structural elucidation and biological activities of surface polysaccharides produced by Burkholderia species. The chemical synthesis of oligosaccharides mimicking Burkholderia polysaccharides is described in detail. Emphasis is placed on the recent research efforts toward the development of glycoconjugate vaccines against melioidosis and glanders based on synthetic or native Burkholderia oligo/polysaccharides.
lipopolysaccharides, Burkholderia, capsular polysaccharides, Oligosaccharides, glycoconjugate vaccines, antigens, exopolysaccharides, surface polysaccharide, virulence factor, Biofilm, chemical synthesis, bioterrorism
Publication DOI: 10.1039/C8NP00046HJournal NLM ID: 8502408Publisher: London: Royal Society of Chemistry
Correspondence: charles.gauthier@iaf.inrs.ca
Institutions: INRS-Institut Armand-Frappier, Universite du Quebec, 531, boul. des Prairies, Laval, Canada
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15. Compound ID: 1283
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115015,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_149135,IEDB_151531,SB_86
The structure is contained in the following publication(s):
- Article ID: 404
Vinion-Dubiel AD, Goldberg JB "Lipopolysaccharide of Burkholderia cepacia complex" -
Journal of Endotoxin Research 9(4) (2003) 201-213
Burkholderia cepacia complex (Bcc) is a group of phenotypically similar, genetically distinct bacteria that are beneficial to the environment but can also cause severe human infections. Bcc are being exploited for use as bioremediation agents and as a way to combat agricultural plant diseases. However, Bcc can cause lung infections in patients with chronic granulomatous disease or cystic fibrosis often resulting in mortality of these patients. Since it is unclear what bacterial components are necessary for causing human infections, studies of Bcc have focused on identifying putative virulence factors. As in other Gram-negative bacteria, the lipopolysaccharide (LPS) of Bcc induces a strong immune response that can contribute to host cell damage. The unusual structure of Bcc LPS lowers the anionic charge of the Bcc cell surface, which inhibits the binding and subsequent effects of cationic antibiotics. These distinguishing features include the substitution of a Ko for a Kdo residue in the inner core oligosaccharide and Ara4N residues bound to phosphates of the lipid A backbone. The structures of O antigen subunits and the consequent serotypes will also be discussed, with particular reference to the O antigen biosynthetic loci of two Bcc strains.
Lipopolysaccharide, structure, Burkholderia, Burkholderia cepacia, O-antigen, complex, endotoxin, Re
NCBI PubMed ID: 12935351Publication DOI: 10.1177/09680519030090040101Journal NLM ID: 9433350Publisher: Maney Publishing
Institutions: Department of Microbiology, University of Virginia Health Sciences Center, Charlottesville, VA 22908-0734, USA
- 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: 1862
Knirel YA, Shashkov AS, Soldatkina MA, Paramonov NA, Zakharova IY "Antigenic polysaccharides of bacteria. 32. Structure of O-specific polysaccharide chains of lipopolysaccharides from Pseudomonas cepacia serotypes B and E containing D-fucose" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 14(9) (1988) 1208-1213
On the basis of acid hydrolysis, methylation, 1H and 13C NMR analysis, and calculation of specific optical rotation, the following structures were established for O-specific polysaccharides of Pseudomonas cepacia serotypes B and E: →3)-β-D-Galf-(1→3)-α-D-Fucp-(1→ serotype B →3)-β-D-GlcpNAc-(1→3)-α-D-Fucp-(1→ serotype E A characteristic feature of the polysaccharides is the presence of D-fucose, rather rare for bacterial antigens.
Journal NLM ID: 7804941WWW link: http://europepmc.org/abstract/med/2464349Publisher: 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: 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: 5143
Cloutier M, Muru K, Ravicoularamin G, Gauthier C "Polysaccharides from Burkholderia species as targets for vaccine development, immunomodulation and chemical synthesis" -
Natural Product Reports 35(12) (2018) 1251-1293
Burkholderia species are a vast group of human pathogenic, phytopathogenic, and plant- or environment-associated bacteria. B. pseudomallei, B. mallei, and B. cepacia complex are the causative agents of melioidosis, glanders, and cystic fibrosis-related infections, respectively, which are fatal diseases in humans and animals. Due to their high resistance to antibiotics, high mortality rates, and increased infectivity via the respiratory tract, B. pseudomallei and B. mallei have been listed as potential bioterrorism agents by the Centers for Disease Control and Prevention. Burkholderia species are able to produce a large network of surface-exposed polysaccharides, i.e., lipopolysaccharides, capsular polysaccharides, and exopolysaccharides, which are virulence factors, immunomodulators, major biofilm components, and protective antigens, and have crucial implications in the pathogenicity of Burkholderia-associated diseases. This review provides a comprehensive and up-to-date account regarding the structural elucidation and biological activities of surface polysaccharides produced by Burkholderia species. The chemical synthesis of oligosaccharides mimicking Burkholderia polysaccharides is described in detail. Emphasis is placed on the recent research efforts toward the development of glycoconjugate vaccines against melioidosis and glanders based on synthetic or native Burkholderia oligo/polysaccharides.
lipopolysaccharides, Burkholderia, capsular polysaccharides, Oligosaccharides, glycoconjugate vaccines, antigens, exopolysaccharides, surface polysaccharide, virulence factor, Biofilm, chemical synthesis, bioterrorism
Publication DOI: 10.1039/C8NP00046HJournal NLM ID: 8502408Publisher: London: Royal Society of Chemistry
Correspondence: charles.gauthier@iaf.inrs.ca
Institutions: INRS-Institut Armand-Frappier, Universite du Quebec, 531, boul. des Prairies, Laval, Canada
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