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1. Compound ID: 58
Structure type: oligomer
Trivial name: Lewisa, Lewis a
Contained glycoepitopes: IEDB_130653,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_149556,IEDB_150899,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423096,IEDB_461723,SB_137,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: 16
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
- Article ID: 230
Feizi T "Progress in deciphering the information content of the 'glycome' - a crescendo in the closing years of the millennium" -
Glycoconjugate Journal 17(7-9) (2000) 553-565
The closing years of the second millennium have been uplifting for carbohydrate biology. Optimism that oligosaccharide sequences are bearers of crucial biological information has been borne out by the constellation of efforts of carbohydrate chemists, biochemists, immunochemists, and cell- and molecular biologists. The direct involvement of specific oligosaccharide sequences in protein targeting and folding, and in mechanisms of infection, inflammation and immunity is now unquestioned. With the emergence of families of proteins with carbohydrate-binding activities, assignments of information content for defined oligosaccharide sequences will become more common, but the pinpointing and elucidation of the bioactive domains on oligosaccharides will continue to pose challenges even to the most experienced carbohydrate biologists. The neoglycolipid technology incorporates some of the key requirements for this challenge: namely the resolution of complex glycan mixtures, and ligand binding coupled with sequence determination by mass spectrometry.
monoclonal antibodies, mass spectrometry, blood group antigen, carbohydrate ligands, differentiation antigens, embryonic development, galectins, inflammation, leukocyte adhesion, neoglycolipids, oligosaccharide ligands, oligosaccharid probes, selectins
NCBI PubMed ID: 11421348Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: t.feizi@ic.ac.uk
Institutions: The Glycosciences Laboratory, Imperial College School of Medicine, Harrow, United Kingdom
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2. Compound ID: 836
Structure type: oligomer
Trivial name: 3'-sialyl-LeA
Contained glycoepitopes: IEDB_130653,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_1391962,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142353,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_146100,IEDB_149174,IEDB_149556,IEDB_150899,IEDB_150933,IEDB_151531,IEDB_152214,IEDB_153235,IEDB_174333,IEDB_190606,IEDB_241110,IEDB_423096,IEDB_461723,SB_116,SB_127,SB_137,SB_155,SB_165,SB_166,SB_170,SB_171,SB_172,SB_186,SB_187,SB_195,SB_29,SB_39,SB_68,SB_7,SB_84,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 230
Feizi T "Progress in deciphering the information content of the 'glycome' - a crescendo in the closing years of the millennium" -
Glycoconjugate Journal 17(7-9) (2000) 553-565
The closing years of the second millennium have been uplifting for carbohydrate biology. Optimism that oligosaccharide sequences are bearers of crucial biological information has been borne out by the constellation of efforts of carbohydrate chemists, biochemists, immunochemists, and cell- and molecular biologists. The direct involvement of specific oligosaccharide sequences in protein targeting and folding, and in mechanisms of infection, inflammation and immunity is now unquestioned. With the emergence of families of proteins with carbohydrate-binding activities, assignments of information content for defined oligosaccharide sequences will become more common, but the pinpointing and elucidation of the bioactive domains on oligosaccharides will continue to pose challenges even to the most experienced carbohydrate biologists. The neoglycolipid technology incorporates some of the key requirements for this challenge: namely the resolution of complex glycan mixtures, and ligand binding coupled with sequence determination by mass spectrometry.
monoclonal antibodies, mass spectrometry, blood group antigen, carbohydrate ligands, differentiation antigens, embryonic development, galectins, inflammation, leukocyte adhesion, neoglycolipids, oligosaccharide ligands, oligosaccharid probes, selectins
NCBI PubMed ID: 11421348Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: t.feizi@ic.ac.uk
Institutions: The Glycosciences Laboratory, Imperial College School of Medicine, Harrow, United Kingdom
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3. Compound ID: 838
Structure type: oligomer
Trivial name: 3'-sulfo-LeA
Contained glycoepitopes: IEDB_130653,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_149556,IEDB_150899,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_241114,IEDB_423096,IEDB_461723,SB_118,SB_137,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: 230
Feizi T "Progress in deciphering the information content of the 'glycome' - a crescendo in the closing years of the millennium" -
Glycoconjugate Journal 17(7-9) (2000) 553-565
The closing years of the second millennium have been uplifting for carbohydrate biology. Optimism that oligosaccharide sequences are bearers of crucial biological information has been borne out by the constellation of efforts of carbohydrate chemists, biochemists, immunochemists, and cell- and molecular biologists. The direct involvement of specific oligosaccharide sequences in protein targeting and folding, and in mechanisms of infection, inflammation and immunity is now unquestioned. With the emergence of families of proteins with carbohydrate-binding activities, assignments of information content for defined oligosaccharide sequences will become more common, but the pinpointing and elucidation of the bioactive domains on oligosaccharides will continue to pose challenges even to the most experienced carbohydrate biologists. The neoglycolipid technology incorporates some of the key requirements for this challenge: namely the resolution of complex glycan mixtures, and ligand binding coupled with sequence determination by mass spectrometry.
monoclonal antibodies, mass spectrometry, blood group antigen, carbohydrate ligands, differentiation antigens, embryonic development, galectins, inflammation, leukocyte adhesion, neoglycolipids, oligosaccharide ligands, oligosaccharid probes, selectins
NCBI PubMed ID: 11421348Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: t.feizi@ic.ac.uk
Institutions: The Glycosciences Laboratory, Imperial College School of Medicine, Harrow, United Kingdom
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4. Compound ID: 1095
Structure type: oligomer
Aglycon: core
Trivial name: Lewis A
Contained glycoepitopes: IEDB_130653,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_149556,IEDB_150899,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423096,IEDB_461723,SB_137,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: 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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5. Compound ID: 1712
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a-L-Fucp-(1-4)-+
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-3)-b-D-GlcpNAc-(1-4)-a-D-GalpA-(1-3)-a-L-Fucp-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_423096,SB_86
The structure is contained in the following publication(s):
- Article ID: 527
Rosen J, Robobi A, Nyholm P "The conformations of the O-specic polysaccharides of Shigella dysenteriae type 4 and Escherichia coli O159 studied with molecular mechanics (MM3)" -
Carbohydrate Research 339 (2004) 961-966
The branched O-antigens of Escherichia coli O159 and Shigella dysenteriae type 4 are structurally related and are known to show cross-reactivity with antibodies. In the present study, conformational analyses were performed on these two O-antigens using molecular mechanics MM3(96) with filtered systematic search. The results show very strong steric restrictions for the trisaccharide at the branch point of the E. coli O159 antigen, especially for the b-D-GlcNAc-(1-3)-b-D-GlcNAc linkage of the main chain. For the type 4 O-antigen the calculations show essentially a single conformation with respect to the a-D-GlcNAc-(1-3)-a-DGlcNAc linkage of the main chain and three different favoured conformations for the fucose branch. Consecutive repeating units of the S. dysenteriae type 4 and E. coli O159 O-antigens form linear extended chains with significant flexibility between the branches. Comparative calculations carried out with the SWEET server indicate that our method of filtered systematic search is a superior method in the case of branched, constrained oligosaccharides. Based on the results of the MM3 calculations, we propose that the common epitope explaining the cross-reactivity comprises the fucose branch, the downstream GlcNAc and part of the uronic acid.
conformation, O-antigen, epitope, Shigella, Molecular mechanics
NCBI PubMed ID: 15010303Publication DOI: 10.1016/j.carres.2003.11.018Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: nyholm@medkem.gu.se
Institutions: Department of Medical Biochemistry/Centre for Structural Biology, Goteborg University, Medicinaregatan 7B, S405 30 Goteborg, Sweden
- Article ID: 3196
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: 3352
Perepelov AV, Liu B, Senchenkova SN, Shashkov AS, Feng L, Knirel YA, Wang L "Close relation of the O-polysaccharide structure of Escherichia coli O168 and revised structure of the O-polysaccharide of Shigella dysenteriae type 4" -
Carbohydrate Research 342(17) (2007) 2676-2681
The O-polysaccharide was isolated from the lipopolysaccharide of Escherichia coli O168 and studied by chemical analyses and Smith degradation along with (1)H and (13)C NMR spectroscopies. The following structure of the branched pentasaccharide repeating unit of the O-polysaccharide was established: [carbohydrate structure: see text] where 6-O-acetylation of GlcNAc is partial. Reinvestigation of the O-polysaccharide of Shigella dysenteriae type 4 established earlier showed it to have the same structure except for that the lateral Fuc residue is nonstoichiometrically O-acetylated at each position.
O-antigen, Escherichia coli, bacterial polysaccharide structure, Shigella dysenteriae, methodology
NCBI PubMed ID: 17880932Publication DOI: 10.1016/j.carres.2007.08.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, chemical analysis, mild acid hydrolysis, Smith degradation, NMR-1D, alkaline hydrolysis
- Article ID: 3530
Perepelov AV, Senchenkova SN, Shashkov AS, Knirel YA, Liu B, Feng L, Wang L "Antigenic polysaccharides of bacteria. 41. Structures of the O-specific polysaccharides of Shigella dysenteriae types 4 and 5 revised by NMR spectroscopy" -
Russian Journal of Bioorganic Chemistry 34(4) (2008) 460-467
The earlier established structures of the acidic O-specific polysaccharides from two typical strains of the Shigella dysenteriae bacterium were revised using modern NMR spectroscopy techniques. In particular, the configurations of the glycosidic linkages of GlcNAc (S. dysenteriae type 4) and mannose (S. dysenteriae type 5) residues were corrected. In addition, the location of the sites of non-stoichiometric O-acetylation in S. dysenteriae type 4 was determined: the lateral fucose residue was shown to be occasionally O-acetylated; also, theposition of the O-acetyl group present at the stoichiometric quantity in S. dysenteriae type 5 was corrected. The revised structures of the polysaccharides studied are shown below. The known identity of theO-specific polysaccharide structures of S. dysenteriae type 5 and Escherichia coli O58 was confirmed by 13C NMR spectroscopy and, hence, the structure of the E. coli O58 polysaccharide should be revised in the same manner.
structure, O-antigen, NMR spectroscopy, O-specific polysaccharide, O-Specific polysaccharide structure, Shigella dysenteriae
NCBI PubMed ID: 18695724Publication DOI: 10.1134/S1068162008040109Journal NLM ID: 9420101Publisher: Springer Science and Business Media
Correspondence: perepel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia,TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, China
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, GLC, mild acid hydrolysis, alkaline degradation, Smith degradation, NMR-1D
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6. Compound ID: 2025
Structure type: oligomer
Aglycon: LPS
Trivial name: Lewis a
Contained glycoepitopes: IEDB_130653,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_149556,IEDB_150899,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423096,IEDB_461723,SB_137,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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7. Compound ID: 2026
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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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8. Compound ID: 2723
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a-L-Fucp-(1-4)-+
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-4)-a-D-GalpA-(1-3)-a-L-Fucp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: suggested polymer biological repeating unit
; 25000, n=~23
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_423096,SB_86
The structure is contained in the following publication(s):
- Article ID: 943
Linnerborg M, Weintraub A, Widmalm G "Structural studies utilizing 13C-enrichment of the O-antigen polysaccharide from the enterotoxigenic Escherichia coli O159 cross-reacting with Shigella dysenteriae type 4" -
European Journal of Biochemistry 266 (1999) 246-251
The structure of the O-antigen polysaccharide from Escherichia coli O159 has been determined using primarily NMR spectroscopy of the 13C-enriched polysaccharide. The sequence of the sugar residues could be determined by heteronuclear multiple bond connectivity NMR experiments. The polysaccharide is composed of a pentasaccharide repeating unit with the following structure: [see structure in text]. Matrix assisted laser desorption ionization mass spectrometry was performed on intact lipopolysaccharide and from the resulting molecular mass the O-antigen part was estimated to contain approximately 23 repeating units. Cross-reactivity of this O-antigen to that of Shigella dysenteriae type 4 was confirmed using enzyme-linked immunoabsorbant assay.
structural, polysaccharide, O-antigen, O antigen, Escherichia, Escherichia coli, enterotoxigenic, type, structural studies, Shigella, Shigella dysenteriae
Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Karolinska Institute, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge University Hospital, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MALDI-MS, determination of absolute configuration
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9. Compound ID: 2846
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
a-L-Fucp-(1-4)-+ | P-7)-+
| | |
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 A determinant
Contained glycoepitopes: IEDB_130650,IEDB_130653,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_149556,IEDB_150899,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423096,IEDB_461723,IEDB_983931,SB_137,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: 2850
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ P-7)-+
| |
a-L-Fucp-(1-3)-a-L-Fucp-(1-4)-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
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423096,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 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: 2854
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
a-L-Fucp-(1-4)-+ |
| |
a-L-Fucp-(1-2)-+ | | EtN-(1--P--7)--+
| | | |
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/ |
Show graphically |
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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12. 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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13. Compound ID: 2861
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ EtN-(1--P--7)--+
| |
a-L-Fucp-(1-3)-a-L-Fucp-(1-4)-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
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423096,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 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
- Article ID: 1006
Monteiro MA, Appelmelk BJ, Rasko DA, Moran AP, Hynes SO, MacLean LL, Chan KH, Michael FS, Logan SM, O'Rourke J, Lee A, Taylor DE, Perry MB "Lipopolysaccharide structures of Helicobacter pylori genomic strains 26695 and J99, mouse model H. pylori Sydney strain, H. pylori P466 carrying sialyl Lewis X, and H. pylori UA915 expressing Lewis B. Classification of H. pylori lipopolysaccharides into glycotype families" -
European Journal of Biochemistry 267(2) (2000) 305-320
This study describes the molecular makeup of the cell-wall lipopolysaccharides (LPSs) (O-chain polysaccharide→core oligosaccharide→lipid A) from five Helicobacter pylori strains: H. pylori 26695 and J99, the complete genome sequences of which have been published, the established mouse model Sydney strain (SS1), and the symptomatic strains P466 and UA915. All chemical and serological experiments were performed on the intact LPSs. H. pylori 26695 and SS1 possessed either a low-Mr semi-rough-form LPS carrying mostly a single Ley type-2 blood-group determinant in the O-chain region covalently attached to the core oligosaccharide or a high-Mr smooth-form LPS, as did strain J99, with an elongated partially fucosylated type-2 N-acetyllactosamine (polyLacNAc) O-chain polymer, terminated mainly by a Lex blood-group determinant, connected to the core oligosaccharide. In the midst of semi-rough-form LPS glycoforms, H. pylori 26695 and SS1 also expressed in the O-chain region a difucosylated antigen, α-L-Fucp(1-3)-α-L-Fucp(1-4)-β-D-GlcpNAc, and the cancer-cell-related type-1 or type-2 linear B-blood-group antigen, α-D-Galp(1-3)-β-D-Galp(1-3 or 4)-β-D-GlcpNAc. The LPS of H. pylori strain P466 carried the cancer-associated type-2 sialyl Lex blood-group antigen, and the LPS from strain UA915 expressed a type-1 Leb blood-group unit. These findings should aid investigations that focus on identifying and characterizing genes responsible for LPS biosynthesis in genomic strains 26695 and J99, and in understanding the role of H. pylori LPS in animal model studies. The LPSs from the H. pylori strains studied to date were grouped into specific glycotype families.
Lipopolysaccharide, structure, Helicobacter pylori, Lewis x, histo-blood groups, glycotypes
NCBI PubMed ID: 10632700Publication DOI: 10.1046/j.1432-1327.2000.01007.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Mario.Monteiro@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada
Methods: FAB-MS, NMR
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14. Compound ID: 2863
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
{{{-a-D-Glcp-(1-6)-}}}a-D-Glcp-(1-2)-+ |
| |
a-L-Fucp-(1-4)-+ | | P-7)-+
| | | |
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 A determinant
Contained glycoepitopes: IEDB_130650,IEDB_130653,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_149556,IEDB_150899,IEDB_151531,IEDB_152214,IEDB_158538,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423096,IEDB_461723,IEDB_983931,SB_137,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
Expand this compound
Collapse this compound
15. Compound ID: 2871
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
{{{-a-D-Glcp-(1-6)-}}}a-D-Glcp-(1-2)-+ | P-7)-+
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a-L-Fucp-(1-4)-b-D-GlcpNAc-(1-3)-D-gro-a-D-manHepp-(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
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152214,IEDB_158538,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423096,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1006
Monteiro MA, Appelmelk BJ, Rasko DA, Moran AP, Hynes SO, MacLean LL, Chan KH, Michael FS, Logan SM, O'Rourke J, Lee A, Taylor DE, Perry MB "Lipopolysaccharide structures of Helicobacter pylori genomic strains 26695 and J99, mouse model H. pylori Sydney strain, H. pylori P466 carrying sialyl Lewis X, and H. pylori UA915 expressing Lewis B. Classification of H. pylori lipopolysaccharides into glycotype families" -
European Journal of Biochemistry 267(2) (2000) 305-320
This study describes the molecular makeup of the cell-wall lipopolysaccharides (LPSs) (O-chain polysaccharide→core oligosaccharide→lipid A) from five Helicobacter pylori strains: H. pylori 26695 and J99, the complete genome sequences of which have been published, the established mouse model Sydney strain (SS1), and the symptomatic strains P466 and UA915. All chemical and serological experiments were performed on the intact LPSs. H. pylori 26695 and SS1 possessed either a low-Mr semi-rough-form LPS carrying mostly a single Ley type-2 blood-group determinant in the O-chain region covalently attached to the core oligosaccharide or a high-Mr smooth-form LPS, as did strain J99, with an elongated partially fucosylated type-2 N-acetyllactosamine (polyLacNAc) O-chain polymer, terminated mainly by a Lex blood-group determinant, connected to the core oligosaccharide. In the midst of semi-rough-form LPS glycoforms, H. pylori 26695 and SS1 also expressed in the O-chain region a difucosylated antigen, α-L-Fucp(1-3)-α-L-Fucp(1-4)-β-D-GlcpNAc, and the cancer-cell-related type-1 or type-2 linear B-blood-group antigen, α-D-Galp(1-3)-β-D-Galp(1-3 or 4)-β-D-GlcpNAc. The LPS of H. pylori strain P466 carried the cancer-associated type-2 sialyl Lex blood-group antigen, and the LPS from strain UA915 expressed a type-1 Leb blood-group unit. These findings should aid investigations that focus on identifying and characterizing genes responsible for LPS biosynthesis in genomic strains 26695 and J99, and in understanding the role of H. pylori LPS in animal model studies. The LPSs from the H. pylori strains studied to date were grouped into specific glycotype families.
Lipopolysaccharide, structure, Helicobacter pylori, Lewis x, histo-blood groups, glycotypes
NCBI PubMed ID: 10632700Publication DOI: 10.1046/j.1432-1327.2000.01007.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Mario.Monteiro@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada
Methods: FAB-MS, NMR
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