Found 272 structures.
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1. Compound ID: 133
Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_141798,IEDB_153201,IEDB_156493,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: 26
Bubb WA, Urashima T, Fujiwara R, Shinnai T, Ariga H "Structural characterization of the extracellular polysaccharide produced by Streptococcus thermophilus OR 901" -
Carbohydrate Research 301(1-2) (1997) 41-50
The exocellular polysaccharide of Streptococcus thermophilus OR 901, isolated from partially deproteinised whey, is a heteropolymer of D-galactopyranose and L-rhamnopyranose residues in the molar ratio 5:2. The structure was established by methylation analysis and 1D and 2D NMR spectroscopy of the native polysaccharide, in combination with characterisation of oligosaccharide fragments, obtained by partial acid hydrolysis, using methylation analysis and 1D 1H NMR spectroscopy. The polysaccharide has a branched heptasaccharide repeating unit with the following structure: [structure]
Lactic acid bacteria, Streptococcus thermophilus, Exopolysaccharide structure, NMR data
NCBI PubMed ID: 9228738Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: wab@biochem.usyd.edu.au
Institutions: Department of Biochemistry, University of Sydney, NSW, Australia
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, acid hydrolysis
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2. Compound ID: 140
Structure type: oligomer
Contained glycoepitopes: IEDB_115136,IEDB_130422,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_140630,IEDB_141798,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 29
Bystrova OV, Zatonsky GV, Borisova SA, Kocharova NA, Shashkov AS, Knirel YA, Kholodkova EV, Stanislavsky ES "Structure of an acidic O-specific polysaccharide of the bacterium Providencia alcalifaciens O7" -
Biochemistry (Moscow) 65(6) (2000) 677-684
An acidic O-specific polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of the bacterium Providencia alcalifaciens O7 and purified by gel chromatography followed by anion-exchange chromatography. On the basis of full acid hydrolysis, methylation, carboxyl reduction, selective cleavage with anhydrous hydrogen fluoride, and 1H- and 13C NMR spectroscopy, including two-dimensional 1H,1H homonuclear and H-detected 1H,13C het-eronuclear correlation spectroscopy and nuclear Overhauser effect spectroscopy (NOESY), the following structure of the linear tetrasaccharide repeating unit of the polysaccharide was established: →4)-p-D-GlcpNAc-(l→3)-a-D-GlcpA-(l→4)-a-D-GlcpNAc-(l→3)-p-L-Rhap2Ac-(1→ where Rhap2Ac is 2-O-acetylrhamnopyranose
Lipopolysaccharide, LPS, structure, polysaccharide, O-antigen, acidic, bacteria, neutral, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens
NCBI PubMed ID: 10887286Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Mechnikov Central Research Institute of Vaccines and Sera, Russian Ministry of Public Health, Pereulok Mechnikova 5a, Moscow, 103064 Russia
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, HF solvolysis, GLC, carboxyl reduction, anion-exchange chromatography
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3. Compound ID: 969
Structure type: oligomer
Contained glycoepitopes: IEDB_136105,IEDB_141798,IEDB_225177,IEDB_885813,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 280
Kaji E, Anabuki N, Zen S "Syntheses of three interglycosidic isomers of N-acetyl-b-D-mannosaminyl-L-rhamnoses associated with O-antigens of several gram-negative opportunistic pathogens" -
Chemical and Pharmaceutical Bulletin 43 (1995) 1441-1447
We achieved practical, highly stereoselective syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl-L-rhamnoses, among which a β(1→4)-isomer corresponds to the repeating unit of the O-antigen of lipopolysaccharide (LPS) from the opportunistic pathogens Pseudomonas cepacia O5 and Pseudomonas aeruginosa X (Meitert). The other isomers are a β(1→2)-disaccharide, a constituent of LPS from Escherichia coli O1A, and an artificial β(1→3)-isomer. The disaccharides were obtained by simple three-step reaction sequences from 2-(benzoyloxyimino)-2-deoxyglycosyl halides (mannosamine progenitor). β-Selective glycosylations of appropriately protected L-rhamnosyl acceptors were performed. Subsequent reduction of the 2-acyloxyimino function to an amino group, N-acetylation, and removal of the protecting groups provided the target disaccharides. 13C NMR and nuclear Overhauser effect spectra proved to be useful for structural determination of the positional isomers of the disaccharides.
Lipopolysaccharide, O-antigen, Gram-negative bacteria, 2-amino-2-deoxy-D-mannose, β-3-D-mannosaminyl-L-rhamnose, 2-uiose oxime, opportunistic infection
NCBI PubMed ID: 7586068Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan, School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan.
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4. Compound ID: 973
Structure type: oligomer
Contained glycoepitopes: IEDB_136105,IEDB_141798,IEDB_225177,IEDB_885813,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 280
Kaji E, Anabuki N, Zen S "Syntheses of three interglycosidic isomers of N-acetyl-b-D-mannosaminyl-L-rhamnoses associated with O-antigens of several gram-negative opportunistic pathogens" -
Chemical and Pharmaceutical Bulletin 43 (1995) 1441-1447
We achieved practical, highly stereoselective syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl-L-rhamnoses, among which a β(1→4)-isomer corresponds to the repeating unit of the O-antigen of lipopolysaccharide (LPS) from the opportunistic pathogens Pseudomonas cepacia O5 and Pseudomonas aeruginosa X (Meitert). The other isomers are a β(1→2)-disaccharide, a constituent of LPS from Escherichia coli O1A, and an artificial β(1→3)-isomer. The disaccharides were obtained by simple three-step reaction sequences from 2-(benzoyloxyimino)-2-deoxyglycosyl halides (mannosamine progenitor). β-Selective glycosylations of appropriately protected L-rhamnosyl acceptors were performed. Subsequent reduction of the 2-acyloxyimino function to an amino group, N-acetylation, and removal of the protecting groups provided the target disaccharides. 13C NMR and nuclear Overhauser effect spectra proved to be useful for structural determination of the positional isomers of the disaccharides.
Lipopolysaccharide, O-antigen, Gram-negative bacteria, 2-amino-2-deoxy-D-mannose, β-3-D-mannosaminyl-L-rhamnose, 2-uiose oxime, opportunistic infection
NCBI PubMed ID: 7586068Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan, School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan.
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5. Compound ID: 974
Structure type: oligomer
Contained glycoepitopes: IEDB_136105,IEDB_141798,IEDB_225177,IEDB_885813,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 280
Kaji E, Anabuki N, Zen S "Syntheses of three interglycosidic isomers of N-acetyl-b-D-mannosaminyl-L-rhamnoses associated with O-antigens of several gram-negative opportunistic pathogens" -
Chemical and Pharmaceutical Bulletin 43 (1995) 1441-1447
We achieved practical, highly stereoselective syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl-L-rhamnoses, among which a β(1→4)-isomer corresponds to the repeating unit of the O-antigen of lipopolysaccharide (LPS) from the opportunistic pathogens Pseudomonas cepacia O5 and Pseudomonas aeruginosa X (Meitert). The other isomers are a β(1→2)-disaccharide, a constituent of LPS from Escherichia coli O1A, and an artificial β(1→3)-isomer. The disaccharides were obtained by simple three-step reaction sequences from 2-(benzoyloxyimino)-2-deoxyglycosyl halides (mannosamine progenitor). β-Selective glycosylations of appropriately protected L-rhamnosyl acceptors were performed. Subsequent reduction of the 2-acyloxyimino function to an amino group, N-acetylation, and removal of the protecting groups provided the target disaccharides. 13C NMR and nuclear Overhauser effect spectra proved to be useful for structural determination of the positional isomers of the disaccharides.
Lipopolysaccharide, O-antigen, Gram-negative bacteria, 2-amino-2-deoxy-D-mannose, β-3-D-mannosaminyl-L-rhamnose, 2-uiose oxime, opportunistic infection
NCBI PubMed ID: 7586068Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan, School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan.
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6. Compound ID: 1967
Structure type: oligomer
Contained glycoepitopes: IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 623
Banaszek A "Synthesis of the unique trisaccharide repeating unit, isolated from lipopolysaccharides Rhizobium leguminosarum bv trifolii 24, and its analogs" -
Carbohydrate Research 306(3) (1998) 379-385
The synthesis of trisaccharide: 6d-a-L-Talp(1-2)-a-L-Rhap(1-5)-DHA, and its analogue: 6d-a-L-Talp(1-2)-b-L-Rhaf(1-5)-DHA is described. In the first step a disaccharide, composed of 6d-L-Talp and L-Rhap was obtained. This, in turn, was converted to the corresponding 1-tri-chloroacetimidate and coupled with DHA alcohol to afford the required trisaccharide. Its analogue was achieved by the conversion of the above disaccharide to the glycosyl bromide, involving the rhamnopyranose ring scission, followed by condensation with DHA in Koenigs-Knorr procedure.
Lipopolysaccharide, trisaccharide, Rhizobium leguminosarum, l-Rhamnopyranose, 6-deoxy-D-talose, DHA
NCBI PubMed ID: 9648246Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224Warsaw, Poland
Methods: NMR, MS
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7. Compound ID: 2144
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a-D-GlcpA-(1-2)-a-D-GalpA-(1-2)-b-D-Manp-(1-4)-b-D-Galp-(1-2)-L-Rha |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137485,IEDB_140630,IEDB_141794,IEDB_141798,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 650
Gloaguen V, Morvan H, Hoffmann L, Plancke Y, Wieruszeski J, Lippens G, Strecker G "Capsular polysaccharide produced by the thermophilic cyanobacterium Mastigocladus laminosus: Structural study of an undecasaccharide obtained by lithium degradation" -
European Journal of Biochemistry 266 (1999) 762-770
The capsular polysaccharide produced by the thermophilic cyanobacterium Mastigocladus laminosus has been subjected to a specific degradation with lithium in ethylenediamine. The released undecasaccharide attached to one unit of tetrahydroxycyclopentanecarboxylic acid has been characterized by a combination of 2D nuclear magnetic resonance spectroscopy, mass spectrometry, monosaccharidic composition and linkage analyses. From the overlap of the structure of this oligosaccharide with previously identified di-, tri- and pentasaccharides released by mild acid hydrolysis, the capsular polysaccharide was deduced to have a pentadecasaccharide repeating unit with the following structure:
NMR, structure, exopolysaccharide, cyanobacterium, lithium degradation
NCBI PubMed ID: 10583369Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: vgloaguen@unilim.fr
Institutions: Equipe de Glycobiologie Vegetale, Institut de Biotechnologie, Université de Limoges, Limoges, France, Cellule de Recherche en Environnement et Biotechnologies, CRP-Centre Universitaire, Luxembourg, Institut de Botanique, Universite de Liege, Liege, Belgium, Laboratoire de Chimie biologique, UMR 111 (CNRS), Universite des Sciences et Techniques Lille Flandres-Artois, France, Centre National de la Recherche Scientifique, URA 1309, Institut Pasteur de Lille, France
Methods: NMR-2D, NMR, mild acid hydrolysis, MS, Li/ethylenediamine degradation
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8. Compound ID: 2565
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R-Lac-(2-3)-+
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-6)-a-D-GlcpNAc-(1-3)-b-L-Rhap-(1-4)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 875
Kocharova NA, Zatonsky GV, Bystrova OV, Ziolkowski A, Wykrota M, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-specific polysaccharide of Providencia alcalifaciens O16 containing N-acetylmuramic acid" -
Carbohydrate Research 337(18) (2002) 1667-1671
The O-specific polysaccharide of Providencia alcalifaciens O16 was obtained by mild-acid degradation of the lipopolysaccharide and studied by chemical methods and NMR spectroscopy, including 2D 1H,(1)H COSY, TOCSY, NOESY, and 1H,(13)C HSQC experiments. It was found that the polysaccharide contains N-acetylmuramic acid, which was isolated by solvolysis with trifluoromethanesulfonic acid and identified by the specific optical rotation and NMR spectroscopy. The following structure of the trisaccharide repeating-unit of the polysaccharide was established:
structure, Bacterial, polysaccharide, acid, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens
NCBI PubMed ID: 12423969Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, triflic acid solvolysis, optical rotation measurement
- Article ID: 3426
Bushmarinov IS, Ovchinnikova OG, Kocharova NA, Toukach FV, Torzewska A, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-polysaccharide and serological cross-reactivity of the lipopolysaccharide of Providencia alcalifaciens O32 containing N-acetylisomuramic acid" -
Carbohydrate Research 342(2) (2007) 268-273
The O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O32 and studied by sugar and methylation analyses, solvolysis with triflic acid, 1H and 13C NMR spectroscopy, including two-dimensional 1H,1H COSY, TOCSY, ROESY, H-detected 1H,13C HSQC and HMBC experiments. It was found that the polysaccharide has a branched tetrasaccharide repeating unit containing 2-acetamido-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose (D-GlcNAc3Slac, N-acetylisomuramic acid) with the following structure: [STRUCTURE: SEE TEXT]. Serological studies with O-antisera showed antigenic relationships between P. alcalifaciens O32 and O29 as well as several other Providencia and Proteus strains sharing putative epitopes on the O-polysaccharides.
Lipopolysaccharide, O-antigen, Providencia alcalifaciens, polysaccharide structure, isomuramic acid
NCBI PubMed ID: 17182016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: olga.ovchinnikova@gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, sugar analysis, mild acid hydrolysis, serological methods, triflic acid solvolysis
- Article ID: 4329
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: 4589
Ovchinnikova OG, Rozalski A, Liu B, Knirel YA "O-Antigens of bacteria of the genus Providencia: structure, serology, genetics, and biosynthesis" -
Biochemistry (Moscow) 78(7) (2013) 798-817
The genus Providencia consists of eight species of opportunistic pathogenic enterobacteria that can cause enteric diseases and urinary tract infections. The existing combined serological classification scheme of three species, P. alcalifaciens, P. stuartii, and P. rustigianii, is based on the specificity of O-antigens (O-polysaccharides) and comprises 63 O-serogroups. Differences between serogroups are related to polymorphism at a specific genome locus, the O-antigen gene cluster, responsible for O-antigen biosynthesis. This review presents data on structures of 36 O-antigens of Providencia, many of which contain unusual monosaccharides and non-carbohydrate components. The structural data correlate with the immunospecificity of the O-antigens and enable substantiation on a molecular level of serological relationships within the genus Providencia and between strains of Providencia and bacteria of the genera Proteus, Escherichia, and Salmonella. Peculiar features of the O-antigen gene cluster organization in 10 Providencia serogroups and biosynthetic pathways of nucleotide precursors of specific monosaccharide components of the O-antigens also are discussed.
Lipopolysaccharide, biosynthesis, O-antigen, gene cluster, Providencia, serological specificity
NCBI PubMed ID: 24010842Publication DOI: 10.1134/S0006297913070110Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: olga.ovchinnikova@gmail.com
Institutions: ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, PL 90-237 Lodz, Poland, TEDA School of Biological Sciences and Biotechnology, Nankai University, 23 Hongda Street, TEDA, 300457 Tianjin, P. R. China
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9. Compound ID: 2573
Structure type: polymer chemical repeating unit
Trivial name: desialylated polysaccharide
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_146668,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 879
Kogan G, Uhrin D, Brisson J, Paoletti LC, Blodgett AE, Kasper DL, Jennings HJ "Structural and immunochemical characterization of the type VIII group B Streptococcus capsular polysaccharide" -
Journal of Biological Chemistry 271(15) (1996) 8786-8790
The type VIII capsular polysaccharide has been isolated and purified from a newly described strain of group B Streptococcus which is a leading cause of sepsis and neonatal meningitis in Japan. The polysaccharide contains D-glucose, D-galactose, L-rhamnose, and sialic acid in the molar ratio 1:1:1:1. By means of high resolution 1H nuclear magnetic resonance (1H NMR), 13C NMR, and homo- and heterocorrelated NMR, the repeating unit structure of the type VIII polysaccharide was delineated as the following, [formula: see text] Enzymatic studies established this polysaccharide as the first from which sialic acid, linked to a branched β-D-galactopyranosyl residue, is known to be removed by bacterial neuraminidase.
NMR, structural, capsular, characterization, polysaccharide, Streptococcus, group, capsular polysaccharide, type, group B Streptococcus, NMR spectroscopy, spectroscopy, elucidation, immunochemical, N-acetylneuraminic acid
NCBI PubMed ID: 8621515Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada
Methods: NMR, enzymatic desialylation
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10. Compound ID: 2667
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60%b-D-GlcpNAc-(1-3)-+
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-3)-b-L-Rhap-(1-4)-b-D-GlcpNAc-(1-6)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 910
Kuebler-Kielb J, Zatonsky GV, Katzenellenbogen E, Kocharova NA, Szostko B, Gamian A, Shashkov AS, Knirel YA "Structure of the O-specific polysaccharide isolated from the lipopolysaccharide of Citrobacter gillenii serotype O12a,12b strain PCM1544" -
Carbohydrate Research 331(3) (2001) 331-336
A neutral O-specific polysaccharide was isolated from the lipopolysaccharide of Citrobacter gillenii strain PCM 1544, representing serotype O12a,12b. The polysaccharide was studied by sugar and methylation analyses and Smith degradation along with 1H and 13C NMR spectroscopy, including a ROESY experiment. The following structure of the tetrasaccharide repeating unit was established, in which substitution with terminal GlcNAc is approximately 60%. [structure: see text].
Lipopolysaccharide, structure, O-antigen, enterobacteria, Citrobacter
NCBI PubMed ID: 11383903Publication DOI: 10.1016/S0008-6215(01)00043-XJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: katzenel@immuno.iitd.pan.wroc.pl
Institutions: L.Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: methylation, NMR, Smith degradation
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11. Compound ID: 2668
Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 910
Kuebler-Kielb J, Zatonsky GV, Katzenellenbogen E, Kocharova NA, Szostko B, Gamian A, Shashkov AS, Knirel YA "Structure of the O-specific polysaccharide isolated from the lipopolysaccharide of Citrobacter gillenii serotype O12a,12b strain PCM1544" -
Carbohydrate Research 331(3) (2001) 331-336
A neutral O-specific polysaccharide was isolated from the lipopolysaccharide of Citrobacter gillenii strain PCM 1544, representing serotype O12a,12b. The polysaccharide was studied by sugar and methylation analyses and Smith degradation along with 1H and 13C NMR spectroscopy, including a ROESY experiment. The following structure of the tetrasaccharide repeating unit was established, in which substitution with terminal GlcNAc is approximately 60%. [structure: see text].
Lipopolysaccharide, structure, O-antigen, enterobacteria, Citrobacter
NCBI PubMed ID: 11383903Publication DOI: 10.1016/S0008-6215(01)00043-XJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: katzenel@immuno.iitd.pan.wroc.pl
Institutions: L.Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: methylation, NMR, Smith degradation
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12. Compound ID: 2669
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Subst-(1-3)-+
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b-L-Rhap-(1-4)-b-D-GlcpNAc-(1-1)-Gro
Subst = CH2OHCH(CH2OH)OCHCH(AcNH)CH2OH = SMILES O{1}C(OC(CO)CO)C(NOC(C)=O)CO |
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Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 910
Kuebler-Kielb J, Zatonsky GV, Katzenellenbogen E, Kocharova NA, Szostko B, Gamian A, Shashkov AS, Knirel YA "Structure of the O-specific polysaccharide isolated from the lipopolysaccharide of Citrobacter gillenii serotype O12a,12b strain PCM1544" -
Carbohydrate Research 331(3) (2001) 331-336
A neutral O-specific polysaccharide was isolated from the lipopolysaccharide of Citrobacter gillenii strain PCM 1544, representing serotype O12a,12b. The polysaccharide was studied by sugar and methylation analyses and Smith degradation along with 1H and 13C NMR spectroscopy, including a ROESY experiment. The following structure of the tetrasaccharide repeating unit was established, in which substitution with terminal GlcNAc is approximately 60%. [structure: see text].
Lipopolysaccharide, structure, O-antigen, enterobacteria, Citrobacter
NCBI PubMed ID: 11383903Publication DOI: 10.1016/S0008-6215(01)00043-XJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: katzenel@immuno.iitd.pan.wroc.pl
Institutions: L.Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: methylation, NMR, Smith degradation
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13. Compound ID: 2670
|
60%b-D-GlcpNAc-(1-3)-+
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-3)-b-L-Rhap2Ac-(1-4)-b-D-GlcpNAc-(1-6)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 910
Kuebler-Kielb J, Zatonsky GV, Katzenellenbogen E, Kocharova NA, Szostko B, Gamian A, Shashkov AS, Knirel YA "Structure of the O-specific polysaccharide isolated from the lipopolysaccharide of Citrobacter gillenii serotype O12a,12b strain PCM1544" -
Carbohydrate Research 331(3) (2001) 331-336
A neutral O-specific polysaccharide was isolated from the lipopolysaccharide of Citrobacter gillenii strain PCM 1544, representing serotype O12a,12b. The polysaccharide was studied by sugar and methylation analyses and Smith degradation along with 1H and 13C NMR spectroscopy, including a ROESY experiment. The following structure of the tetrasaccharide repeating unit was established, in which substitution with terminal GlcNAc is approximately 60%. [structure: see text].
Lipopolysaccharide, structure, O-antigen, enterobacteria, Citrobacter
NCBI PubMed ID: 11383903Publication DOI: 10.1016/S0008-6215(01)00043-XJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: katzenel@immuno.iitd.pan.wroc.pl
Institutions: L.Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: methylation, NMR, Smith degradation
- Article ID: 1468
Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" -
Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity
NCBI PubMed ID: 12546064Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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14. Compound ID: 2684
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a-D-GalpNAc-(1-4)-+
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b-D-GlcpNAc-(1-3)-a-D-GalpNAc-(1-3)-a-D-GalpNAc-(1-2)-L-Rha |
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Structure type: oligomer
Trivial name: repeating unit of the O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_1391965,IEDB_141582,IEDB_141584,IEDB_141798,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_423113,IEDB_885822,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 918
Landersjo C, Widmalm G "Solution structure of a pentasaccharide representing the repeating unit of the O-antigen polysaccharide from Escherichia coli O142: NMR spectroscopy and molecular simulation studies" -
Biopolymers 64(6) (2002) 283-291
Conformational studies have been performed of a pentasaccharide derived from the O-polysaccharide from Escherichia coli O142. The polymer was selectively degraded by anhydrous hydrogen fluoride and reduced to yield an oligosaccharide model of its repeating unit, which in the branching region consists of four aminosugars. A comparison of (1)H and (13)C chemical shifts between the pentasaccharide and the polymer showed only minor differences, except where the cleavage had taken place, indicating that the oligomer is a good model of the repeating unit. Langevin dynamics and molecular dynamics simulations with explicit water molecules were carried out to sample the conformational space of the pentasaccharide. For the glycosidic linkages between the hexopyranoside residues, small but significant changes were observed between the simulation techniques. One-dimensional (1D) (1)H,(1)H double pulsed field gradient spin echo (DPFGSE) transverse rotating- frame Overhauser effect spectroscopy (T-ROESY) experiments were performed, and homonuclear cross-relaxation rates were obtained. Subsequently, a comparison of interproton distances from NMR experiment and the two simulation approaches showed that in all cases the use of explicit water in the simulations resulted in better agreement. Hydrogen-bond analysis of the trajectories from the molecular dynamics simulation revealed interresidue interactions to be important as a cluster of different hydrogen bonds and as a distinct highly populated hydrogen bond. NMR data are consistent with the presence of hydrogen bonding within the model of the repeating unit
NMR, oligosaccharide, structure, chemistry, polysaccharide, O-antigen, repeating unit, analysis, O antigen, hydrogen, hydrogen bond, molecular, molecule, polymer, water, Escherichia, Escherichia coli, glycosidic linkage, conformational, dynamics, molecular dynamics, NMR spectroscopy, cluster, O-polysaccharide, O polysaccharide, linkage, chemical, region, reduced, spectroscopy, interaction, difference, pentasaccharide, comparison, solution, case, change, simulation, effect, Overhauser effect, organic, model, use, cleavage, approach, chemical shift, chemical shifts, distance, Hydrogen Bonding, hydrogen fluoride, Langevin dynamics, rotating frame, shift
NCBI PubMed ID: 12124846Journal NLM ID: 0372525Publisher: Wiley Interscience
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: NMR-2D, NMR, MS, MD simulations, solvolysis
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15. Compound ID: 2741
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b-L-Rhap-(1-4)-+
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-3)-a-D-GlcpNAc-(1--P--6)--a-D-Glcp-(1-2)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_150077,IEDB_151531,IEDB_225177,IEDB_241118,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 959
MacLean LL, Perry MB "Structural studies on the O-polysaccharide of the lipopolysaccharide produced by Citrobacter rodentium (ATCC51459)" -
European Journal of Biochemistry 268(22) (2001) 5740-5746
Citrobacter rodentium is the etiologic agent of transmissible murine colonic hyperplasia (TMCH) and is the only Citrobacter species known to possess virulence factors homologous to human enteropathogenic and enterohemorrhagic Escherichia coli. Members of this species are considered clonal and represent the only known attaching and effacing bacterial pathogen of mice and thus provides a useful animal model for studying the molecular basis of attaching and effacing pathology. The lipopolysaccharide (LPS) produced by C. rodentium has not been previously studied or its possible role as a virulence factor determined. The structure of the LPS has been undertaken as a first step in an investigation of its possible role in pathogenesis. The structure of C. rodentium (ATCC51459, prototype TMCH isolate, original biotype 4280, previously designated DBS 100) LPS was determined from composition and methylation analyses, mass spectrometry, and two-dimensional nuclear magnetic resonance spectroscopy. The antigenic O-polysaccharide was found to be a high molecular mass branched polymer of repeating pentasaccharide units composed of 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), d-glucose (D-Glc), and L-rhamnose (L-Rha) in the molar ratio 2 : 2 : 1 linked through phosphate, and has the structure: [structure: see text]
Lipopolysaccharide, strain, structural, O-polysaccharide, O polysaccharide, structural studies, Citrobacter
NCBI PubMed ID: 11722558Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: malcolm.perry@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A 0R6.
Methods: methylation, NMR-2D, NMR, MS, composition analysis
- Article ID: 1468
Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" -
Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity
NCBI PubMed ID: 12546064Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1548
Olsson U, Lycknert K, Stenutz R, Weintraub A, Widmalm G "Structural analysis of the O-antigen polysaccharide from Escherichia coli O152" -
Carbohydrate Research 340(1) (2005) 167-171
The structure of the O-antigen polysaccharide (PS) from Escherichia coli O152 has been determined. Component analysis together with (1)H, (13)C and (31)P NMR spectroscopy were used to elucidate the structure. Inter-residue correlations were determined by (1)H,(31)P COSY, (1)H,(1)H NOESY and (1)H,(13)C heteronuclear multiple-bond correlation experiments. The PS is composed of pentasaccharide repeating units with the following structure: The structure is similar to that of the O-antigen polysaccharide from E. coli O173. The cross-reactivity between E. coli O152 and E. coli O3 may be explained by structural similarities in the branching region of their O-antigen polysaccharides
NMR, structure, chemistry, correlation, structural, polysaccharide, O-antigen, repeating unit, analysis, O antigen, Escherichia, Escherichia coli, NMR spectroscopy, structural analysis, polysaccharides, region, spectroscopy, pentasaccharide, component, similarity, cross-reactivity, crossreactivity, organic, NOESY, COSY, heteronuclear
NCBI PubMed ID: 15620681Publication DOI: 10.1016/j.carres.2004.11.008Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Bacteriology, F-82 Karolinska University Hospital, Huddinge Stockholm, Sweden
Methods: NMR, composition analysis
- Article ID: 3197
Stenutz R, Weintraub A, Widmalm G "The structures of Escherichia coli O-polysaccharide antigens" -
FEMS Microbiology Reviews 30(3) (2006) 382-403
Escherichia coli is usually a non-pathogenic member of the human colonic flora. However, certain strains have acquired virulence factors and may cause a variety of infections in humans and in animals. There are three clinical syndromes caused by E. coli: (i) sepsis/meningitis; (ii) urinary tract infection and (iii) diarrhoea. Furthermore the E. coli causing diarrhoea is divided into different 'pathotypes' depending on the type of disease, i.e. (i) enterotoxigenic; (ii) enteropathogenic; (iii) enteroinvasive; (iv) enterohaemorrhagic; (v) enteroaggregative and (vi) diffusely adherent. The serotyping of E. coli based on the somatic (O), flagellar (H) and capsular polysaccharide antigens (K) is used in epidemiology. The different antigens may be unique for a particular serogroup or antigenic determinants may be shared, resulting in cross-reactions with other serogroups of E. coli or even with other members of the family Enterobacteriacea. To establish the uniqueness of a particular serogroup or to identify the presence of common epitopes, a database of the structures of O-antigenic polysaccharides has been created. The E. coli database (ECODAB) contains structures, nuclear magnetic resonance chemical shifts and to some extent cross-reactivity relationships. All fields are searchable. A ranking is produced based on similarity, which facilitates rapid identification of strains that are difficult to serotype (if known) based on classical agglutinating methods. In addition, results pertinent to the biosynthesis of the repeating units of O-antigens are discussed. The ECODAB is accessible to the scientific community at http://www.casper.organ.su.se/ECODAB/
NMR, structure, serotype, O-antigen, Enterobacteriacea, database
NCBI PubMed ID: 16594963Publication DOI: 10.1111/j.1574-6976.2006.00016.xJournal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: andrej.weintraub@ki.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
- Article ID: 3365
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
- Article ID: 3446
Brockhausen I, Hu B, Liu B, Lau K, Szarek WA, Wang L, Feng L "Characterization of two b-1,3-glucosyltransferases from Escherichia coli serotypes O56 and O152" -
Journal of Bacteriology 190(14) (2008) 4922-4932
The O antigens of outer membrane-bound lipopolysaccharides (LPS) in Gram-negative bacteria are oligosaccharides consisting of repeating units with various structures and antigenicities. The O56 and O152 antigens of Escherichia coli both contain a Glc-β 1-3-GlcNAc linkage within the repeating unit. We have cloned and identified the genes (wfaP in O56 and wfgD in O152) within the two O antigen gene clusters that encode glucosyltransferases involved in the synthesis of this linkage. A synthetic substrate analog of the natural acceptor substrate undecaprenol-pyrophosphate-lipid (GlcNAc-PP-PhU) was used as an acceptor and UDP-Glc as a donor substrate to demonstrate that both wfgD and wfaP encode glucosyltransferases. Enzyme products from both glucosyltransferases were isolated by HPLC and analyzed by NMR. The spectra showed the expected Glc-β 1-3-GlcNAc linkage in the products, confirming that both WfaP and WfgD are UDP-Glc: GlcNAc-pyrophosphate-lipid β-1,3-glucosyltransferases. Both WfaP and WfgD have a DxD sequence which is proposed to interact with phosphate groups of the nucleotide donor through the coordination of a metal cation, and a short hydrophobic sequence at the C terminus that may help to associate the enzymes with the inner membrane. We showed that the enzymes have similar properties and substrate recognition. They both require divalent cation (Mn(2+) or Mg(2+)) for activity, are deactivated by detergents, have a broad pH optimum, and require the pyrophosphate-sugar linkage in the acceptor substrate for full activity. Substrates lacking phosphate or pyrophosphate linked to GlcNAc were inactive. The length of the aliphatic chain of acceptor substrates also contributes to the activity.
O-antigen, gene cluster, Glucosyltransferases, enzymatic syntheses, Escherichia coli O56, Escherichia coli O152
NCBI PubMed ID: 18487334Publication DOI: 10.1128/JB.00160-08Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: fenglu63@nankai.edu.cn
Institutions: Department of Medicine, Department of Biochemistry, Queen's University, Kingston Ontario K7L 3N6, Canada, TEDA School of Biological Sciences and Biotechnology, Nankai University, Hongda Street, TEDA, Tianjin 300457, P.R.China, Tianjin Key Laboratory of Microbial Functional Genomics, P. R. China, Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, P. R. China, Department of Chemistry, Queen's University, Kingston Ontario K7L 3N6, Canada
Methods: 13C NMR, 1H NMR, genetic methods, biochemical methods, HPLC
- Article ID: 3506
Liu B, Knirel YA, Feng L, Perepelov AV, Senchenkova SN, Wang Q, Reeves P, Wang L "Structure and genetics of Shigella O antigens" -
FEMS Microbiology Reviews 32(4) (2008) 627-653
This review covers the O antigens of the 46 serotypes of Shigella, but those of most Shigella flexneri are variants of one basic structure, leaving 34 Shigella distinct O antigens to review, together with their gene clusters. Several of the structures and gene clusters are reported for the first time and this is the first such group for which structures and DNA sequences have been determined for all O antigens. Shigella strains are in effect Escherichia coli with a specific mode of pathogenicity, and 18 of the 34 O antigens are also found in traditional E. coli. Three are very similar to E. coli O antigens and 13 are unique to Shigella strains. The O antigen of Shigella sonnei is quite atypical for E. coli and is thought to have transferred from Plesiomonas. The other 12 O antigens unique to Shigella strains have structures that are typical of E. coli, but there are considerably more anomalies in their gene clusters, probably reflecting recent modification of the structures. Having the complete set of structures and genes opens the way for experimental studies on the role of this diversity in pathogenicity.
structure, O antigen, Shigella, O antigen gene cluster, O antigen diversity
NCBI PubMed ID: 18422615Publication DOI: 10.1111/j.1574-6976.2008.00114.xJournal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: wanglei@nankai.edu.cn
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China.
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, serological methods, genetic methods, biochemical methods
- Article ID: 4329
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: 5472
Liu B, Furevi A, Perepelov AV, Guo X, Cao H, Wang Q, Reeves PR, Knirel YA, Wang L, Widmalm G "Structure and genetics of Escherichia coli O antigens" -
FEMS Microbiology Reviews 44(6) (2020) 655-683
Escherichia coli includes clonal groups of both commensal and pathogenic strains, with some of the latter causing serious infectious diseases. O antigen variation is current standard in defining strains for taxonomy and epidemiology, providing the basis for many serotyping schemes for Gram-negative bacteria. This review covers the diversity in E. coli O antigen structures and gene clusters, and the genetic basis for the structural diversity. Of the 187 formally defined O antigens, six (O31, O47, O67, O72, O94 and O122) have since been removed and four (O14, O34, O89 and O144) strains do not produce any O antigen. Therefore, structures are presented for 176 of the 181 E. coli O antigens, some of which include subgroups. Most (93%) of these O antigens are synthesized via the Wzx/Wzy pathway, 11 via the ABC transporter pathway, with O20, O57 and O60 still uncharacterized due to failure to find their O antigen gene clusters. Biosynthetic pathways are given for 38 of the 49 sugars found in E. coli O antigens, and several pairs or groups of the E. coli antigens that have related structures show close relationships of the O antigen gene clusters within clades, thereby highlighting the genetic basis of the evolution of diversity.
structure, O antigen, Escherichia coli, gene cluster, serogroup, diversity
NCBI PubMed ID: 31778182Publication DOI: 10.1093/femsre/fuz028Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: G. Widmalm
; Lei Wang
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Immunology, School of Basic Medical Sciences, Tianjin Medical University, Tianjin, China
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