Found 46 structures.
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1. Compound ID: 350
a-L-Fucp-(1-2)-+
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a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc |
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Structure type: fragment of a bigger structure
Trivial name: monofucosyl A type 1 histo-blood group epitope
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_885822,SB_100,SB_137,SB_149,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 99
Therisod H, Monteiro MA, Perry MB, Caroff M "Helicobacter mustelae lipid A structure differs from that of Helicobacter pylori" -
FEBS Letters 499(1-2) (2001) 1-5
The lipid A structure of the Gram-negative bacterium Helicobacter mustelae, a ferret gastric pathogen responsible for the onset of gastric diseases in its host, was investigated. Two variant lipid A structures were found in the same strain. One structure contained a bisphosphorylated β-(1→6)-linked D-glucosamine backbone disaccharide with hydroxytetradecanoic acid in amide linkages. Unlike the structure described for the lipid A of the related human Helicobacter pylori gastric pathogen, which contains a C1 phosphate moiety, this lipid A presented phosphate groups at both the C1 and C4' positions, and contained no octadecanoyl fatty acid, which is present in H. pylori. The second lipid A structure had a different fatty acid composition in that 3-OH C(16) replaced most of the amide-linked 3-OH C(14).
structure, lipid A, endotoxin, Helicobacter mustelae, Helicobacter pylori
NCBI PubMed ID: 11418100Publication DOI: 10.1016/S0014-5793(01)02496-6Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: martine.caroff@bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, Biochimie, Université de Paris-Sud, Orsay, France, Institute for Biological Sciences, National Research Council of Canada, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, de-O-acylation, TLC, 31P NMR, GC, MALDI-TOF MS, composition analysis, PD-MS, NMR-1D
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2. Compound ID: 1100
Structure type: oligomer
Aglycon: core
Trivial name: Lewis D
Contained glycoepitopes: IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461709,IEDB_461719,SB_100,SB_137,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 329
Monteiro MA, Chan KHN, Rasko DA, Taylor DE, Zheng PY, Appelmelk BJ, Wirth HP, Yang MQ, Blaser MJ, Hynes SO, Moran AP, Perry MB "Simultaneous expression of type 1 and type 2 Lewis blood group antigens by Helicobacter pylori lipopolysaccharides" -
Journal of Biological Chemistry 273(19) (1998) 11533-11543
Previous structural investigations performed on the lipopolysaccharides (LPSs) from the human gastric pathogen Helicobacter pylori have revealed that these cell surface glycan molecules express type 2 partially fucosylated, glucosylated, or galactosylated N-acetyllactosamine O antigen chains (O-chains) of various lengths, which may or may not be terminated at the nonreducing end by Lewis X (Lex) and/or Ley blood group epitopes in mimicry of human cell surface glycoconjugates and glycolipids. Subsequently, serological experiments with commercially available Lewis-specific monoclonal antibodies also have recognized the presence of Lex and Ley blood group antigens in H. pylori but, in addition, have indicated the presence of type 1 chain Lea, Leb, and Led (H-type 1) blood group epitopes in some H. pylori strains. To confirm their presence, structural studies and additional serological experiments were undertaken on H. pylori strains suspected of carrying type 1 chain epitopes. These investigations revealed that the O-chain region of H. pylori strain UA948 carried both Lea (type 1) and Lex (type 2) blood group determinants. The O-chain from H. pylori UA955 LPS expressed the terminal Lewis disaccharide (type 1 chain) and Lex and Ley antigens (type 2). The O-chain of H. pylori J223 LPS carried the type 1 chain precursor Lec, the H-1 epitope (Led, type 1 chain) and an elongated nonfucosylated type 2 N-acetyllactosamine chain (i antigen). Thus, O-chains from H. pylori LPSs can also express fucosylated type 1 sequences, and the LPS from a single H. pylori strain may carry O-chains with type 1 and 2 Lewis blood groups simultaneously. That monoclonal antibodies putatively specific for the Leb determinant can detect glycan substructures (Le disaccharide, Lec, and Led) of Leb indicates their nonspecificity. The expression of both type 1 and 2 Lewis antigens by H. pylori LPSs mimics the cell surface glycomolecules present in both the gastric superficial (which expresses mainly type 1 determinants) and the superficial and glandular epithelium regions (both of which express predominantly type 2 determinants). Therefore, each H. pylori strain may have a different niche within the gastric mucosa, and each individual LPS blood group antigen may have a dissimilar role in H. pylori adaptation.
antigen, lipopolysaccharides, expression, type, Helicobacter pylori, Helicobacter, Lewis, blood group antigens
NCBI PubMed ID: 9565568Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: Mario.Monteiro@nrc.ca
Institutions: Department of Microbiology, National University of Ireland, Galway, Ireland, Canadian Bacterial Diseases Network, b Institute for Biological Sciences, National Research Council, Ottawa, K1A 0R6 Ontario, Canada, Department of Medical Microbiology and Immunology, University of Alberta, Edmonton, T6G 2H7 Alberta, Canada, Department of Medical Microbiology, Vrije Universiteit Amsterdam, Amsterdam, The Netherlands, Division of Gastroenterology, Zurich University Scool of Medicine, Zurich, Switzerland, Department of Medicine, Vanderbilt University and Veterans Affairs Medical Center, Nashville, Tennessee
Methods: 1H NMR, FAB-MS, ELISA, GLC, immunoblotting
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3. Compound ID: 1748
a-L-Fucp-(1-2)-+
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-2)-b-D-Manp-(1-3)-b-D-Galp-(1-3)-a-D-GlcpNAc-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_149554,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152206,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461719,IEDB_983930,SB_100,SB_137,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_44,SB_7,SB_72,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 539
Larsson EA, Urbina F, Yang Z, Weintraub A, Widmalm G "Structural and immunochemical relationship between the O-antigenic polysaccharides from the enteroaggregative Escherichia coli strain 396/C-1 and Escherichia coli O126" -
Carbohydrate Research 339(8) (2004) 1491-1496
The structure of the O-antigen polysaccharide (PS) from the enteroaggregative Escherichia coli strain 396/C-1 has been determined. Sugar and methylation analyses together with (1)H and (13)C NMR spectroscopy were the main methods used. Inter-residue correlations were determined by (1)H,(1)H-NOESY, (1)H,(13)C-heteronuclear multiple-bond correlation and dipole-dipole cross-correlated relaxation experiments. The PS is composed of pentasaccharide repeating units with the following structure: Analysis of NMR data reveals that on average the PS consists of approximately 13 repeating units and indicates that the biological repeating unit contains an N-acetylglucosamine residue at its reducing end. This structure is different to that reported for the O-antigen polysaccharide from E. coli O126. Monospecific anti-E. coli O126 rabbit serum from The International Escherichia and Klebsiella Centre did not distinguish between the E. coli strain 396/C-1 and the E. coli O126 reference strain, neither in slide agglutination nor in an indirect enzyme immunoassay. Subsequent successful serotyping of the E. coli strain 396/C-1 showed it to be E. coli O126:K+:H27.
Lipopolysaccharide, NMR, Escherichia coli, serology, Enteroaggregative
NCBI PubMed ID: 15178392Publication DOI: 10.1016/j.carres.2004.04.002Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis
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4. Compound ID: 1866
a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1--/lipopolysaccharide/ |
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Structure type: oligomer
Aglycon: lipopolysaccharide
Trivial name: Lewis H type 1
Contained glycoepitopes: IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461709,IEDB_461719,SB_100,SB_137,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 603
Appelmelk BJ, Martino MC, Veenhof E, Monteiro MA, Maaskant JJ, Negrini R, Lindh F, Perry MB, del Guidice G, Vandenbroucke-Grauls CMJE "Phase variation in H type 1 and Lewis a epitopes of Helicobacter pylori lipopolysaccharide" -
Infection and Immunity 68(10) (2000) 5928-5932
Helicobacter pylori NCTC11637 lipopolysaccharide (LPS) expresses the human blood group antigens Lewis x (Lex), Ley, and H type I. In this report, we demonstrate that the H type I epitope displays high-frequency phase variation. One variant expressed Lex and Ley and no H type I as determined by serology; this switch was reversible. Insertional mutagenesis in NCTC11637 of JHP563 (a poly(C) tract containing an open reading frame homologous to glycosyltransferases) yielded a transformant with a serotype similar to the phase variant. Structural analysis of the NCTC11637 LPS confirmed the loss of the H type I epitope. Sequencing of JHP563 in strains NCTC11637, an H type I-negative variant, and an H type I-positive switchback variant showed a C14 (gene on), C13 (gene off), and C14 tract, respectively. Inactivation of strain G27, which expresses Lex, Ley, H type I, and Lea, yielded a transformant that expressed Lex and Ley. We conclude that JHP563 encodes a b3-galactosyltransferase involved in the biosynthesis of H type I and Lea and that phase variation in H type I is due to C-tract changes in this gene. A second H type I-negative variant (variant 3a) expressed Lex and Lea and had lost both H type I and Ley expression. Inactivation of HP093-HP094 resulted in a transformant expressing Lex and lacking Ley and H type I. Structural analysis of a mutant LPS confirmed the serological data. We conclude that the HP093-HP094 a2-fucosyltransferase (a2-Fuct) gene product is involved in the biosynthesis of both Ley and Lex. Finally, we inactivated HP0379 in strain 3a. The transformant had lost both Lex and Lea expression, which demonstrates that the HP0379 gene product is both an a3- and an a4-FucT. Our data provide understanding at the molecular level of how H. pylori is able to diversify in the host, a requirement likely essential for successful colonization and transmission.
Lipopolysaccharide, Phase variation, gene, phase, tract, variation, epitope, type, epitopes, Helicobacter pylori, Helicobacter, change, Lewis, fucosyltransferase, Lewis a
NCBI PubMed ID: 10992504Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Medical School, 1081 BT Amsterdam, The Netherlands, IRIS Research Center, Chiron SpA, Siena, Laboratory Unit, City Hospital, Brescia, Italy, National Research Council, Ottawa, Canada, Isosep, Tullinge, Sweden
Methods: PCR, DNA sequencing, FAB-MS, ELISA, MAb studies, insertional mutagenesis
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5. Compound ID: 2026
a-L-Fucp-(1-4)-+
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a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1--/LPS/ |
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Structure type: oligomer
Aglycon: LPS
Trivial name: Lewis b
Contained glycoepitopes: IEDB_130652,IEDB_130653,IEDB_131182,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137354,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_149556,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_423096,IEDB_461709,IEDB_461719,IEDB_461723,IEDB_461724,SB_100,SB_137,SB_146,SB_154,SB_155,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 603
Appelmelk BJ, Martino MC, Veenhof E, Monteiro MA, Maaskant JJ, Negrini R, Lindh F, Perry MB, del Guidice G, Vandenbroucke-Grauls CMJE "Phase variation in H type 1 and Lewis a epitopes of Helicobacter pylori lipopolysaccharide" -
Infection and Immunity 68(10) (2000) 5928-5932
Helicobacter pylori NCTC11637 lipopolysaccharide (LPS) expresses the human blood group antigens Lewis x (Lex), Ley, and H type I. In this report, we demonstrate that the H type I epitope displays high-frequency phase variation. One variant expressed Lex and Ley and no H type I as determined by serology; this switch was reversible. Insertional mutagenesis in NCTC11637 of JHP563 (a poly(C) tract containing an open reading frame homologous to glycosyltransferases) yielded a transformant with a serotype similar to the phase variant. Structural analysis of the NCTC11637 LPS confirmed the loss of the H type I epitope. Sequencing of JHP563 in strains NCTC11637, an H type I-negative variant, and an H type I-positive switchback variant showed a C14 (gene on), C13 (gene off), and C14 tract, respectively. Inactivation of strain G27, which expresses Lex, Ley, H type I, and Lea, yielded a transformant that expressed Lex and Ley. We conclude that JHP563 encodes a b3-galactosyltransferase involved in the biosynthesis of H type I and Lea and that phase variation in H type I is due to C-tract changes in this gene. A second H type I-negative variant (variant 3a) expressed Lex and Lea and had lost both H type I and Ley expression. Inactivation of HP093-HP094 resulted in a transformant expressing Lex and lacking Ley and H type I. Structural analysis of a mutant LPS confirmed the serological data. We conclude that the HP093-HP094 a2-fucosyltransferase (a2-Fuct) gene product is involved in the biosynthesis of both Ley and Lex. Finally, we inactivated HP0379 in strain 3a. The transformant had lost both Lex and Lea expression, which demonstrates that the HP0379 gene product is both an a3- and an a4-FucT. Our data provide understanding at the molecular level of how H. pylori is able to diversify in the host, a requirement likely essential for successful colonization and transmission.
Lipopolysaccharide, Phase variation, gene, phase, tract, variation, epitope, type, epitopes, Helicobacter pylori, Helicobacter, change, Lewis, fucosyltransferase, Lewis a
NCBI PubMed ID: 10992504Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Medical School, 1081 BT Amsterdam, The Netherlands, IRIS Research Center, Chiron SpA, Siena, Laboratory Unit, City Hospital, Brescia, Italy, National Research Council, Ottawa, Canada, Isosep, Tullinge, Sweden
Methods: PCR, DNA sequencing, FAB-MS, ELISA, MAb studies, insertional mutagenesis
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6. Compound ID: 2844
a-L-Fucp-(1-2)-+
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a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1--/lipopolysacharide core/ |
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Structure type: oligomer
Aglycon: lipopolysacharide core
Trivial name: monofucosyl A type 1 histo-blood group epitope
Contained glycoepitopes: IEDB_130648,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_885822,SB_100,SB_137,SB_149,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1003
Monteiro MA, Zheng PY, Appelmelk BJ, Perry MB "The lipopolysaccharide of Helicobacter mustelae type strain ATCC43772 expresses the monofucosyl A type 1 histo-blood group epitope" -
FEMS Microbiology Letters 154(1) (1997) 103-109
Lipopolysaccharide, LPS, structure, strain, O-antigen, group, structural determination, epitope, type, molecular mimicry, Helicobacter mustelae, Helicobacter, blood group A
Journal NLM ID: 7705721Publisher: Blackwell Publishing
Correspondence: Mario.Monteiro@nrc.ca
Institutions: Canadian Bacterial Diseases Network, Institute for Biological Sciences,National Research Council Canada,Ottawa,Canada
Methods: NMR, MS
- Article ID: 4690
Knirel YA, Gabius H, Blixt O, Rapoport EM, Khasbiullina NR, Shilova NV, Bovin NV "Human tandem-repeat-type galectins bind bacterial non-bGal polysaccharides" -
Glycoconjugate Journal 31(1) (2014) 7-12
Galectins are multifunctional effectors, for example acting as regulators of cell growth via protein-glycan interactions. The observation of capacity to kill bacteria for two tandem-repeat-type galectins, which target histo-blood epitopes toward this end (Stowell et al. Nat. Med. 16:295-301, 2010), prompted us to establish an array with bacterial polysaccharides. We addressed the question whether sugar determinants other than ?-galactosides may be docking sites, using human galectins-4, -8, and -9. Positive controls with histo-blood group ABH-epitopes and the E. coli 086 polysaccharide ascertained the suitability of the set-up. Significant signal generation, depending on type of galectin and polysacchride, was obtained. Presence of cognate ?-galactoside-related epitopes within a polysaccharide chain or its branch will not automatically establish binding properties, and structural constellations lacking galactosides, like rhamnan, were found to be active. These data establish the array as valuable screening tool, giving direction to further functional and structural studies.
glycan, Bacterial polysaccharide, ABO, galectin, printed glycan array, rhamnoside
NCBI PubMed ID: 24065176Publication DOI: 10.1007/s10719-013-9497-3Journal NLM ID: 8603310WWW link: doi:10.1007/s10719-013-9497-3Publisher: Kluwer Academic Publishers
Correspondence: bovin@carb.ibch.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp., 47, Moscow, Russian Federation, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10
Methods: GPC, mild acid degradation, binding assays
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7. Compound ID: 2853
a-L-Fucp-(1-2)-+ a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ EtN-(1--P--7)--+
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a-D-GalpNAc-(1-3)-b-D-Gal-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 monofucosyl A blood-group determinant
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140088,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_885822,IEDB_983931,SB_100,SB_137,SB_149,SB_154,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1005
Monteiro MA, Zheng P, Ho B, Yokota S, Amano K, Pan Z, Berg DE, Chan KH, MacLean LL, Perry MB "Expression of histo-blood group antigens by lipopolysaccharides of Helicobacter pylori strains from Asian hosts: the propensity to express type 1 blood-group antigens" -
Glycobiology 10(7) (2000) 701-713
Past studies have shown that the cell surface lipopolysaccharides (LPSs) of the ubiquitous human gastric pathogen Helicobacter pylori (a type 1 carcinogen) isolated from people residing in Europe and North America express predominantly type 2 Lewis x (Le(x)) and Le(y) epitopes and, infrequently, type 1 Le(a), Le(b), and Le(d) antigens. This production of Lewis blood-group structures by H. pylori LPSs, similar to those found in the surfaces of human gastric cells, allows the bacterium to mimic its human niche. In this study, LPSs of H.pylori strains extracted from patients living in China, Japan, and Singapore were chemically and serologically analyzed. When compared with Western H.pylori LPSs, these Asian strains showed a stronger tendency to produce type 1 blood groups. Of particular interest, and novel observations in H.pylori, the O-chain regions of strains F-58C and R-58A carried type 1 Le(a) without the presence of type 2 Le(x), strains R-7A and H607 were shown to have the capability of producing the type 1 blood group A antigen, and strains CA2, H507, and H428 expressed simultaneously the difucosyl isomeric antigens, type 1 Le(b) and type 2 Le(y). The apparent proclivity for the production of type 1 histo-blood group antigens in Asian H.pylori LPSs, as compared with Western strains, may be an adaptive evolutionary effect in that differences in the gastric cell surfaces of the respective hosts might be significantly dissimilar to select for the formation of different LPS structures on the resident H.pylori strain.
lipopolysaccharides, structural determination, Helicobacter pylori, histo-blood groups
NCBI PubMed ID: 10910974Publication DOI: 10.1093/glycob/10.7.701Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Microbiology, National University of Singapore, Singapore, Central Research Laboratory, Akita University School of Medicine, Akita, Japan, Departments of Molecular Microbiology and Genetics, Washington University School of Medicine, St. Louis, MO 63130, USA
Methods: FAB-MS, NMR
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8. Compound ID: 2854
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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a-L-Fucp-(1-4)-+ |
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a-L-Fucp-(1-2)-+ | | EtN-(1--P--7)--+
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a-D-GalpNAc-(1-3)-b-D-Gal-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 difucosyl A blood-group determinant
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130652,IEDB_130653,IEDB_131182,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_137340,IEDB_137354,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140088,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_149556,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_157005,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423096,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_461723,IEDB_461724,IEDB_885822,IEDB_983931,SB_100,SB_102,SB_137,SB_146,SB_149,SB_154,SB_155,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1005
Monteiro MA, Zheng P, Ho B, Yokota S, Amano K, Pan Z, Berg DE, Chan KH, MacLean LL, Perry MB "Expression of histo-blood group antigens by lipopolysaccharides of Helicobacter pylori strains from Asian hosts: the propensity to express type 1 blood-group antigens" -
Glycobiology 10(7) (2000) 701-713
Past studies have shown that the cell surface lipopolysaccharides (LPSs) of the ubiquitous human gastric pathogen Helicobacter pylori (a type 1 carcinogen) isolated from people residing in Europe and North America express predominantly type 2 Lewis x (Le(x)) and Le(y) epitopes and, infrequently, type 1 Le(a), Le(b), and Le(d) antigens. This production of Lewis blood-group structures by H. pylori LPSs, similar to those found in the surfaces of human gastric cells, allows the bacterium to mimic its human niche. In this study, LPSs of H.pylori strains extracted from patients living in China, Japan, and Singapore were chemically and serologically analyzed. When compared with Western H.pylori LPSs, these Asian strains showed a stronger tendency to produce type 1 blood groups. Of particular interest, and novel observations in H.pylori, the O-chain regions of strains F-58C and R-58A carried type 1 Le(a) without the presence of type 2 Le(x), strains R-7A and H607 were shown to have the capability of producing the type 1 blood group A antigen, and strains CA2, H507, and H428 expressed simultaneously the difucosyl isomeric antigens, type 1 Le(b) and type 2 Le(y). The apparent proclivity for the production of type 1 histo-blood group antigens in Asian H.pylori LPSs, as compared with Western strains, may be an adaptive evolutionary effect in that differences in the gastric cell surfaces of the respective hosts might be significantly dissimilar to select for the formation of different LPS structures on the resident H.pylori strain.
lipopolysaccharides, structural determination, Helicobacter pylori, histo-blood groups
NCBI PubMed ID: 10910974Publication DOI: 10.1093/glycob/10.7.701Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Microbiology, National University of Singapore, Singapore, Central Research Laboratory, Akita University School of Medicine, Akita, Japan, Departments of Molecular Microbiology and Genetics, Washington University School of Medicine, St. Louis, MO 63130, USA
Methods: FAB-MS, NMR
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9. Compound ID: 2858
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
a-L-Fucp-(1-4)-+ | P-7)-+
| | |
a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 Lewis B determinant
Contained glycoepitopes: IEDB_130650,IEDB_130652,IEDB_130653,IEDB_131182,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137354,IEDB_137472,IEDB_1391962,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_149556,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423096,IEDB_461709,IEDB_461719,IEDB_461723,IEDB_461724,IEDB_983931,SB_100,SB_137,SB_146,SB_154,SB_155,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1005
Monteiro MA, Zheng P, Ho B, Yokota S, Amano K, Pan Z, Berg DE, Chan KH, MacLean LL, Perry MB "Expression of histo-blood group antigens by lipopolysaccharides of Helicobacter pylori strains from Asian hosts: the propensity to express type 1 blood-group antigens" -
Glycobiology 10(7) (2000) 701-713
Past studies have shown that the cell surface lipopolysaccharides (LPSs) of the ubiquitous human gastric pathogen Helicobacter pylori (a type 1 carcinogen) isolated from people residing in Europe and North America express predominantly type 2 Lewis x (Le(x)) and Le(y) epitopes and, infrequently, type 1 Le(a), Le(b), and Le(d) antigens. This production of Lewis blood-group structures by H. pylori LPSs, similar to those found in the surfaces of human gastric cells, allows the bacterium to mimic its human niche. In this study, LPSs of H.pylori strains extracted from patients living in China, Japan, and Singapore were chemically and serologically analyzed. When compared with Western H.pylori LPSs, these Asian strains showed a stronger tendency to produce type 1 blood groups. Of particular interest, and novel observations in H.pylori, the O-chain regions of strains F-58C and R-58A carried type 1 Le(a) without the presence of type 2 Le(x), strains R-7A and H607 were shown to have the capability of producing the type 1 blood group A antigen, and strains CA2, H507, and H428 expressed simultaneously the difucosyl isomeric antigens, type 1 Le(b) and type 2 Le(y). The apparent proclivity for the production of type 1 histo-blood group antigens in Asian H.pylori LPSs, as compared with Western strains, may be an adaptive evolutionary effect in that differences in the gastric cell surfaces of the respective hosts might be significantly dissimilar to select for the formation of different LPS structures on the resident H.pylori strain.
lipopolysaccharides, structural determination, Helicobacter pylori, histo-blood groups
NCBI PubMed ID: 10910974Publication DOI: 10.1093/glycob/10.7.701Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Microbiology, National University of Singapore, Singapore, Central Research Laboratory, Akita University School of Medicine, Akita, Japan, Departments of Molecular Microbiology and Genetics, Washington University School of Medicine, St. Louis, MO 63130, USA
Methods: FAB-MS, NMR
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10. Compound ID: 2859
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ P-7)-+
| |
a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 Lewis D determinant
Contained glycoepitopes: IEDB_130650,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_461709,IEDB_461719,IEDB_983931,SB_100,SB_137,SB_154,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1005
Monteiro MA, Zheng P, Ho B, Yokota S, Amano K, Pan Z, Berg DE, Chan KH, MacLean LL, Perry MB "Expression of histo-blood group antigens by lipopolysaccharides of Helicobacter pylori strains from Asian hosts: the propensity to express type 1 blood-group antigens" -
Glycobiology 10(7) (2000) 701-713
Past studies have shown that the cell surface lipopolysaccharides (LPSs) of the ubiquitous human gastric pathogen Helicobacter pylori (a type 1 carcinogen) isolated from people residing in Europe and North America express predominantly type 2 Lewis x (Le(x)) and Le(y) epitopes and, infrequently, type 1 Le(a), Le(b), and Le(d) antigens. This production of Lewis blood-group structures by H. pylori LPSs, similar to those found in the surfaces of human gastric cells, allows the bacterium to mimic its human niche. In this study, LPSs of H.pylori strains extracted from patients living in China, Japan, and Singapore were chemically and serologically analyzed. When compared with Western H.pylori LPSs, these Asian strains showed a stronger tendency to produce type 1 blood groups. Of particular interest, and novel observations in H.pylori, the O-chain regions of strains F-58C and R-58A carried type 1 Le(a) without the presence of type 2 Le(x), strains R-7A and H607 were shown to have the capability of producing the type 1 blood group A antigen, and strains CA2, H507, and H428 expressed simultaneously the difucosyl isomeric antigens, type 1 Le(b) and type 2 Le(y). The apparent proclivity for the production of type 1 histo-blood group antigens in Asian H.pylori LPSs, as compared with Western strains, may be an adaptive evolutionary effect in that differences in the gastric cell surfaces of the respective hosts might be significantly dissimilar to select for the formation of different LPS structures on the resident H.pylori strain.
lipopolysaccharides, structural determination, Helicobacter pylori, histo-blood groups
NCBI PubMed ID: 10910974Publication DOI: 10.1093/glycob/10.7.701Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Microbiology, National University of Singapore, Singapore, Central Research Laboratory, Akita University School of Medicine, Akita, Japan, Departments of Molecular Microbiology and Genetics, Washington University School of Medicine, St. Louis, MO 63130, USA
Methods: FAB-MS, NMR
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11. Compound ID: 3626
a-L-Fucp-(1-4)-+
|
a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-Glcp-(1--/acetylphenylenediamine-HSA/ |
Show graphically |
Structure type: oligomer
Aglycon: acetylphenylenediamine-HSA
Trivial name: Lewis b antigen determinant
Compound class: neoglycoconjugate
Contained glycoepitopes: IEDB_117715,IEDB_130652,IEDB_130653,IEDB_131182,IEDB_135511,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137354,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141499,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_142489,IEDB_143248,IEDB_143249,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_149556,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_157001,IEDB_174333,IEDB_190606,IEDB_226432,IEDB_423095,IEDB_423096,IEDB_461709,IEDB_461719,IEDB_461723,IEDB_461724,IEDB_983931,SB_100,SB_137,SB_145,SB_146,SB_150,SB_153,SB_154,SB_155,SB_156,SB_160,SB_161,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1358
Appelmelk BJ, Simoons-Smit I, Negrini R, Moran AP, Aspinall GO, Forte JG, de Vries T, Quan H, Verboom T, Maaskant JJ, Ghiara P, Kuipers EJ, Bloemena E, Tadema TM, Townsend RR, Tyagarajan K, Crothers JM, Monteiro MA, Savio A, De Graaf J "Potential role of molecular mimicry between Helicobacter pylori lipopolysaccharide and host Lewis blood group antigens in autoimmunity" -
Infection and Immunity 64 (1996) 2031-2040
Helicobacter pylori is involved in gastritis, gastric and duodenal ulcers, gastric adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma. Earlier studies already suggested a role for autoimmune phenomena in H. pylori-linked disease. We now report that lipopolysaccharides (LPS) of H. pylori express Lewis y, Lewis x, and H type I blood group structures similar to those commonly occurring in gastric mucosa. Immunization of mice and rabbits with H. pylori cells or purified LPS induced an anti-Lewis x or y or anti-H type I response, yielding antibodies that bound human and murine gastric glandular tissue, granulocytes, adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma cells. Experimental oral infections in mice or natural infection in humans yielded anti-Lewis antibodies also. The beta chain of gastric (H+,K+)-ATPase, the parietal cell proton pump involved in acid secretion, contained Lewis y epitopes; gastric mucin contained Lewis x and y antigenic determinants. Growth in mice of a hybridoma that secretes H. pylori-induced anti-Lewis y monoclonal antibodies resulted in histopathological evidence of gastritis, which indicates a direct pathogenic role for anti-Lewis antibodies. In conclusion, our observations demonstrate that molecular mimicry between H. pylori LPS and the host, based on Lewis antigens, and provide understanding of an autoimmune mechanism for H. pylori-associated type B gastritis.
Lipopolysaccharide, antigen, LPS, potential, molecular mimicry, Helicobacter pylori, S-type LPS, Lewis x, blood group antigens
NCBI PubMed ID: 8675304Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Medical School, Amsterdam, The Netherlands
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12. Compound ID: 3630
a-L-Fucp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-Glcp-(1--/acetylphenylenediamine-HSA/ |
Show graphically |
Structure type: oligomer
Aglycon: acetylphenylenediamine-HSA
Trivial name: H type I antigen
Compound class: neoglycoconjugate
Contained glycoepitopes: IEDB_117715,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_1391966,IEDB_141794,IEDB_141807,IEDB_142076,IEDB_142078,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_142489,IEDB_143249,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_157001,IEDB_174333,IEDB_190606,IEDB_423095,IEDB_461709,IEDB_461719,IEDB_983931,SB_100,SB_137,SB_145,SB_153,SB_154,SB_156,SB_165,SB_166,SB_173,SB_174,SB_187,SB_192,SB_195,SB_29,SB_6,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1358
Appelmelk BJ, Simoons-Smit I, Negrini R, Moran AP, Aspinall GO, Forte JG, de Vries T, Quan H, Verboom T, Maaskant JJ, Ghiara P, Kuipers EJ, Bloemena E, Tadema TM, Townsend RR, Tyagarajan K, Crothers JM, Monteiro MA, Savio A, De Graaf J "Potential role of molecular mimicry between Helicobacter pylori lipopolysaccharide and host Lewis blood group antigens in autoimmunity" -
Infection and Immunity 64 (1996) 2031-2040
Helicobacter pylori is involved in gastritis, gastric and duodenal ulcers, gastric adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma. Earlier studies already suggested a role for autoimmune phenomena in H. pylori-linked disease. We now report that lipopolysaccharides (LPS) of H. pylori express Lewis y, Lewis x, and H type I blood group structures similar to those commonly occurring in gastric mucosa. Immunization of mice and rabbits with H. pylori cells or purified LPS induced an anti-Lewis x or y or anti-H type I response, yielding antibodies that bound human and murine gastric glandular tissue, granulocytes, adenocarcinoma, and mucosa-associated lymphoid tissue lymphoma cells. Experimental oral infections in mice or natural infection in humans yielded anti-Lewis antibodies also. The beta chain of gastric (H+,K+)-ATPase, the parietal cell proton pump involved in acid secretion, contained Lewis y epitopes; gastric mucin contained Lewis x and y antigenic determinants. Growth in mice of a hybridoma that secretes H. pylori-induced anti-Lewis y monoclonal antibodies resulted in histopathological evidence of gastritis, which indicates a direct pathogenic role for anti-Lewis antibodies. In conclusion, our observations demonstrate that molecular mimicry between H. pylori LPS and the host, based on Lewis antigens, and provide understanding of an autoimmune mechanism for H. pylori-associated type B gastritis.
Lipopolysaccharide, antigen, LPS, potential, molecular mimicry, Helicobacter pylori, S-type LPS, Lewis x, blood group antigens
NCBI PubMed ID: 8675304Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Medical School, Amsterdam, The Netherlands
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13. Compound ID: 3960
a-L-Fucp-(1-2)-+
|
-3)-b-D-Ribf-(1-4)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-4)-a-L-Fucp3Ac-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149136,IEDB_149554,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_423153,IEDB_461709,IEDB_461719,SB_100,SB_137,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1467
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: 2244
Shashkov AS, Vinogradov EV, Knirel YA, Nifant'ev NE, Kochetkov NK, Dabrowski J, Kholodkova EV, Stanislavsky ES "Structure of the O-specific polysaccharide of Salmonella arizonae O45" -
Carbohydrate Research 241 (1993) 177-188
The O-specific polysaccharide of Salmonella arizonae O45 (Arizona 11) is acidic and has a branched hexasaccharide repeating unit containing two residues of L-fucose, one residue each of D-galactose, D-ribose, D-glucuronic acid, and 2-acetamido-2-deoxy-D-glucose, and an O-acetyl group. It was studied with the help of 1H and 13C NMR spectroscopy, including 1D selective spin-decoupling and homonuclear Hartmann-Hahn spectroscopy, 2D homonuclear and 13C-1H heteronuclear shift-correlated (COSY) and NOE (ROESY) spectroscopy, as well as by methylation analysis, and selective cleavages with anhydrous HF (or dilute HCl) and lithium in ethylenediamine to yield two different tetrasaccharide fragments. As a result, the following structure of the polysaccharide was established: [formula: see text] Anomalous 13C chemical shifts were observed in the spectrum of the trisaccharide fragment α-L-Fucp-(1→2)-β-D-Galp-(1→3)-β-D-GlcpNAc, structurally related to the Le(d) blood-group determinant, and rationalised by inter-residue proton-proton interactions.
NCBI PubMed ID: 7682473Publication DOI: 10.1016/0008-6215(93)80104-mJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, partial acid hydrolysis, HF solvolysis, de-O-acetylation, GPC, Li/ethylenediamine degradation
- Article ID: 5461
Knirel YA, Naumenko OI, Senchenkova SN, Perepelov AV "Chemical methods for selective cleavage of glycosidic linkages in structural analysis of bacterial polysaccharides" -
Russian Chemical Reviews = Uspekhi Khimii 88(4) (2019) 406-424
This review is devoted to methods for the selective cleavage of glycosidic bonds. The mechanisms of reactions underlying these methods are considered and examples of their practical application in the structural analysis of bacterial polysaccharides are given. Specific methods for the selective cleavage of polysaccharides, remaining relevant for researchers, include the Smith degradation based on destruction of monosaccharides containing vicinal diol groups, dephosphorylation of phosphate-containing polysaccharides with hydrofluoric acid and the hydrolytic cleavage of glycosyl phosphate bonds in the latter compounds. Non-specific methods, including partial acid hydrolysis, acetolysis and solvolysis with anhydrous organic (CF3SO3H, MeSO3H, CF3CO2H) and inorganic (HF) acids do not make any specific demands on the composition and structure of the polysaccharide and are sensitive to its fine structural features. The review addesses the issue of stability of glycosidic bonds in various monosaccharides to reagents used for non-specific selective cleavage.
structural analysis, Bacterial polysaccharide, selective cleavage, glycosidic bond
Publication DOI: 10.1070/RCR4856Journal NLM ID: 0404506Publisher: London: Chemical Society
Correspondence: Yu.A. Knirel
Institutions: N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
Methods: partial acid hydrolysis, HF solvolysis, acid hydrolysis, mild acid hydrolysis, alkaline degradation, b-elimination, Smith degradation, deamination, de-O-acetylation, HF treatment, reduction with NaBD4, triflic acid solvolysis, acetolysis, Li/ethylenediamine degradation, hydrazinolysis, reduction with NaBH4, mild acid degradation, trifluoroacetic acid solvolysis, partial solvolysis with anhydrous trifluoroacetic acid, de-N-acetylation with hydrazine, part acid hydrolysis, HF solvolysis; published polymerization frame was shifted for conformity with other records.
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14. Compound ID: 4330
8%a-L-Fucp-(1-3)-+ a-L-Fuc-(1-3)-+
| |
a-L-Fuc-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-{{{-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-}}}/n=12/-b-D-Galp-(1-4)-b-D-GlcpNAc-(1--/core ID 10796/
|
/Variants 0/-+
/Variants 0/ is:
45%a-D-Glcp-(1-6)-
OR (exclusively)
15%a-D-Galp-(1-6)- |
Show graphically |
Structure type: oligomer
; n=12
Aglycon: core ID 10796
Contained glycoepitopes: IEDB_130646,IEDB_130652,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391962,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_142489,IEDB_143794,IEDB_144556,IEDB_144562,IEDB_144998,IEDB_145669,IEDB_146664,IEDB_147455,IEDB_149554,IEDB_149557,IEDB_150092,IEDB_150899,IEDB_150939,IEDB_150948,IEDB_151528,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461709,IEDB_461719,IEDB_461720,IEDB_952752,IEDB_983931,SB_100,SB_137,SB_154,SB_157,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_29,SB_30,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1625
Khamri W, Moran AP, Worku ML, Karim QN, Walker MM, Annuk H, Ferris JA, Appelmelk BJ, Eggleton P, Reid KB, Thursz MR "Variations in Helicobacter pylori lipopolysaccharide to evade the innate immune component surfactant protein D" -
Infection and Immunity 73(11) (2005) 7677-7686
Helicobacter pylori is a common and persistent human pathogen of the gastric mucosa. Surfactant protein D (SP-D), a component of innate immunity, is expressed in the human gastric mucosa and is capable of aggregating H. pylori. Wide variation in the SP-D binding affinity to H. pylori has been observed in clinical isolates and laboratory-adapted strains. The aim of this study was to reveal potential mechanisms responsible for evading SP-D binding and establishing persistent infection. An escape variant, J178V, was generated in vitro, and the lipopolysaccharide (LPS) structure of the variant was compared to that of the parental strain, J178. The genetic basis for structural variation was explored by sequencing LPS biosynthesis genes. SP-D binding to clinical isolates was demonstrated by fluorescence-activated cell sorter analyses. Here, we show that H. pylori evades SP-D binding through phase variation in lipopolysaccharide. This phenomenon is linked to changes in the fucosylation of the O chain, which was concomitant with slipped-strand mispairing in a poly(C) tract of the fucosyltransferase A (fucT1) gene. SP-D binding organisms are predominant in mucus in vivo (P = 0.02), suggesting that SP-D facilitates physical elimination. Phase variation to evade SP-D contributes to the persistence of this common gastric pathogen.
lipopolysaccharides, Helicobacter pylori, immunity, Innate, Pulmonary Surfactant-Associated Protein D
NCBI PubMed ID: 16239572Publication DOI: 10.1128/IAI.73.11.7677-7686.2005Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: wafa.khamri@imperial.ac.uk
Institutions: Imperial College Faculty of Medicine, St Mary's Campus, Norfolk Place, London, W2 1PG, United Kingdom
Methods: methylation, NMR, sugar analysis, MS
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15. Compound ID: 5392
Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461709,IEDB_461719,SB_100,SB_137,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 2244
Shashkov AS, Vinogradov EV, Knirel YA, Nifant'ev NE, Kochetkov NK, Dabrowski J, Kholodkova EV, Stanislavsky ES "Structure of the O-specific polysaccharide of Salmonella arizonae O45" -
Carbohydrate Research 241 (1993) 177-188
The O-specific polysaccharide of Salmonella arizonae O45 (Arizona 11) is acidic and has a branched hexasaccharide repeating unit containing two residues of L-fucose, one residue each of D-galactose, D-ribose, D-glucuronic acid, and 2-acetamido-2-deoxy-D-glucose, and an O-acetyl group. It was studied with the help of 1H and 13C NMR spectroscopy, including 1D selective spin-decoupling and homonuclear Hartmann-Hahn spectroscopy, 2D homonuclear and 13C-1H heteronuclear shift-correlated (COSY) and NOE (ROESY) spectroscopy, as well as by methylation analysis, and selective cleavages with anhydrous HF (or dilute HCl) and lithium in ethylenediamine to yield two different tetrasaccharide fragments. As a result, the following structure of the polysaccharide was established: [formula: see text] Anomalous 13C chemical shifts were observed in the spectrum of the trisaccharide fragment α-L-Fucp-(1→2)-β-D-Galp-(1→3)-β-D-GlcpNAc, structurally related to the Le(d) blood-group determinant, and rationalised by inter-residue proton-proton interactions.
NCBI PubMed ID: 7682473Publication DOI: 10.1016/0008-6215(93)80104-mJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, partial acid hydrolysis, HF solvolysis, de-O-acetylation, GPC, Li/ethylenediamine degradation
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