Found 65 structures.
Displayed structures from 1 to 15
Next 15 structure(s)
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 1024
|
a-L-Fucp-(1-3)-+
|
a-L-Fucp-(1-2)-{{{-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-}}}D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1--/(1->7)aXDDmanHeppII of core oligosaccharide -lipid A (ID 7468)/ |
Show graphically |
Structure type: oligomer
Aglycon: (1->7)aXDDmanHeppII of core oligosaccharide -lipid A (ID 7468)
Trivial name: O-chain region
Contained glycoepitopes: IEDB_130644,IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_143250,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149555,IEDB_149557,IEDB_149561,IEDB_150092,IEDB_150787,IEDB_150939,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_158546,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_2189046,IEDB_461719,IEDB_461720,IEDB_461721,IEDB_952752,SB_147,SB_154,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_34,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 310
Logan SM, Conlan JW, Monteiro MA, Wakarchuk WW, Altman E "Functional genomics of Helicobacter pylori: identification of a b-1,4 galactosyltransferase and generation of mutants with altered lipopolysaccharide" -
Molecular Microbiology 35(5) (2000) 1156-1167
A previously annotated open reading frame (ORF) (HP0826) from Helicobacter pylori was cloned and expressed in Escherichia coli cells and determined to be a β-1,4-galactosyltransferase that used GlcNAc as an acceptor. Mutational analysis in H. pylori strains demonstrated that this enzyme plays a key role in the biosynthesis of the type 2 N-acetyl-lactosamine (LacNAc) polysaccharide O-chain backbone, by catalysing the addition of Gal to GlcNAc. To examine the potential role of this O-chain structure in bacterial colonization of the host stomach, the mutation was introduced into H. pylori strain SS1 which is known to be capable of colonizing the gastric mucosa of mice. Compared with the parental strain, mutated SS1 was less efficient at colonizing the murine stomach.
Lipopolysaccharide, mutants, Helicobacter pylori, galactosyltransferase, Helicobacter, genomics
NCBI PubMed ID: 10712696Publication DOI: 10.1046/j.1365-2958.2000.01784.xJournal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: susan.logan@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada, K1A OR6.
Methods: methylation, FAB-MS
Expand this compound
Collapse this compound
2. Compound ID: 1093
Structure type: polymer chemical repeating unit
Aglycon: core
Trivial name: poly(Lewis X)
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,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
- Article ID: 613
Aspinall GO, Monteiro MA "Lipopolysaccharides of Helicobacter pylori strains P466 and MO19: Structures of the O antigen and core oligosaccharide regions" -
Biochemistry 35 (1996) 2498-2504
Lipopolysaccharides (LPS) from phenol-water extraction of dyspeptic (P466) and asymptomatic (MO19) strains of Helicobacter pylori were each isolated as water-soluble material of high relative molecular mass (high Mr) and as water-insoluble gels of low Mr. Chemical and spectroscopic analyses of the soluble LPS and oligosaccharides liberated from the water-insoluble gels led to proposed structures for chains comprising the O antigen, intervening, and core regions. As in the LPS from the type strain NCTC11637 [Aspinall, G. O., et al. (1996) Biochemistry 35, 000], the O antigen region of the P466 LPS is characterized by the presence of extended chains with fucosylated and nonfucosylated N-acetyllactosamine units, the former carrying a-L-fucopyranose units at O-3 of b-D-GlcNAc residues. This structure differs from that of the type strain in termination of the O chain by a Lewisy (Ley) antigenic determinant [a-LFuc(1-2)b-D-Gal(1-4)[a-L-Fuc(1-3)]b-D-GlcNAc] but also has internal Lewisx (Lex) units. The inner core region of the P466 LPS is indistinguishable from that in the type strain. In contrast, the O antigen region of the LPS from strain MO19 consists of a single Ley epitope linked via a 3-linked b-D-Gal to an intervening region on the basis of a sequence of 3-linked D-glycero-a-D-manno-heptose residues which is in turn linked to an inner core identical to that in the type strain and the P466 strain. Results in this and the preceding paper show that LPS from the three H. pylori strains display molecular mimicry of human cell surface glycoconjugates but may vary in the expression of Lex or Ley determinants, the degree of O antigen chain extension, or in the presence of an additional region between the inner core and the O antigen.
Lipopolysaccharide, antigen, lipopolysaccharides, LPS, oligosaccharide, structure, core, strain, O-antigen, O antigen, core oligosaccharide, region, Helicobacter pylori, Helicobacter
NCBI PubMed ID: 8652594Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Chemistry, York University, North York, Toronto, Ontario M3J 1P3, Canada
Methods: NMR-2D, defucosylation
- Article ID: 615
Aspinall GO, Mainkar AS, Moran AP "A structural comparison of lipopolysaccharides from two strains of Helicobacter pylori, of which one strain (442) does and the other strain (471) does not stimulate pepsinogen secretion" -
Glycobiology 9(11) (1999) 1235-1245
Lipopolysaccharides (LPSs) from strains of Helicobacter pylori (442 and 471), which differed in stimulation of pepsinogen secretion, were isolated as water-soluble material of high-Mr, and as water-insoluble gels of low-Mr. Chemical and spectroscopic analyses of soluble LPS and oligosaccharides liberated from the gels led to proposed structures with Lewis (Le) antigen termini connected to N-acetyllactosaminoglycans of alternating 3-linked b-D-Gal and 4-linked b-D-GlcNAc residues with various laterally attached glycosyl substituents. The LPS of H.pylori 442 was similar to previously examined strains (NCTC11637 and P466) in having partially glycosylated chains with a-L-Fuc units attached to O-3 of the majority of GlcNAc residues in Lex units, and in chain termination with Lex or Ley determinants. In contrast, terminal Ley units occurred in LPS of H.pylori 471 and glycosaminoglycan chains carried a smaller proportion of a-L-Fuc units, but at O-6 of a majority of nonfucosylated GlcNAc residues, there was a novel type of branching with a-D-Gal substituents. Evidence for the branched regions was obtained from 1H NMR spectra and from characterization of oligosaccharides formed by the action of endo-β-galactosidase. Examination of oligosaccharides liberated from water-insoluble LPS gels of H.pylori 442 and 471 provided evidence for similar core OS structures to those from other H.pylori strains but interesting differences were observed.
Lipopolysaccharide, lipopolysaccharides, strain, structural, Helicobacter pylori, comparison, Helicobacter, pepsinogen, secretion
NCBI PubMed ID: 10536039Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Microbiology, National University of Ireland, Galway, Ireland, Department of Chemistry, York University, North York, ON M3J 1P3, Canada
Methods: NMR-2D, FAB-MS, Smith degradation, enzymatic degradation, defucosylation
Expand this compound
Collapse this compound
3. Compound ID: 1450
|
a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+
| | |
a-L-Fucp-(1-2)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-{{{-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-}}}{{{-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-}}}b-D-Galp-(1-4)-b-D-GlcpNAc-(1--/(1->7)aDDHepp-core oligosaccharide/ |
Show graphically |
Structure type: oligomer
Aglycon: (1->7)aDDHepp-core oligosaccharide
Trivial name: O-side chain antigen
Contained glycoepitopes: IEDB_130644,IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_143250,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149555,IEDB_149557,IEDB_149561,IEDB_150092,IEDB_150939,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461719,IEDB_461720,IEDB_461721,IEDB_952752,SB_147,SB_154,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_34,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 461
Moran AP, Shiberu B, Ferris JA, Knirel YA, Senchenkova SN, Perepelov AV, Jansson P, Goldberg JB "Role of Helicobacter pylori rfaJ genes (HP0159 and HP1416) in lipopolysaccharide synthesis" -
FEMS Microbiology Letters 241(1) (2004) 57-65
The genome of Helicobacter pylori 26695 has been sequenced and the lipopolysaccharide (LPS) O sidechain of this strain has been shown to express both Lewis x and Lewis y units. To determine the role of HP0159 and HP1416, genes recognized as rfaJ homologs and implicated in LPS synthesis, isogenic mutants of H. pylori 26695 were generated. The LPS of mutant 26695::HP0159Kan did not express either Lewis epitope as detected by immunoblotting, whereas the control strain and 26695::HP1416Kan produced both epitopes. Structural analysis of the LPS of the mutants showed that HP0159 encodes an α(1,2/3)-glucosyltransferase whereas HP1416 encodes an α(1,2/4)-glucosyltransferase.
Lipopolysaccharide, core oligosaccharide, Helicobacter pylori, glycosyltransferase, Lewis antigen
NCBI PubMed ID: 15556710Publication DOI: 10.1016/j.femsle.2004.10.004Journal NLM ID: 7705721Publisher: Blackwell Publishing
Correspondence: jbg2b@virginia.edu
Institutions: Department of Microbiology, National University of Ireland, Galway, Ireland
Expand this compound
Collapse this compound
4. Compound ID: 1875
Structure type: polymer chemical repeating unit
; 638-432
Aglycon: core
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 612
Aspinall GO, Monteiro MA, Pang H, Walsh EJ, Moran AP "Lipopolysaccharide of the Helicobacter pylori type strain NCTC11637 (ATCC43504): Structure of the O antigen chain and core oligosaccharide regions" -
Biochemistry 35 (1996) 2489-2497
Smooth- and rough-form lipopolysaccharides from phenol-water extraction of cells from Helicobacter pylori type strain NCTC11637 were isolated as the water-soluble component of high-Mr and water-insoluble low-Mr gel. Structural investigations were performed on the intact water-soluble smooth-form lipopolysaccharide, various oligosaccharides formed as chemical and enzymic degradation products, and three oligosaccharide fractions liberated by acetic acid hydrolysis from the water-insoluble rough-form lipopolysaccharide. A structure is proposed for the complete polysaccharide component of the smooth-form lipopolysaccharide comprising the O antigen chain, an intervening region, and the inner core oligosaccharide on the basis of 1H and 13C NMR experiments, fast atom bombardment/mass spectrometry, and methylation linkage analysis of permethylated oligo- and polysaccharide derivatives. The most striking feature of the O antigen region in the lipopolysaccharide is the presence of extended chains with fucosylated and nonfucosylated N-acetyllactosamine (LacNAc) units that mimic human cell surface glycoconjugates in normal human granulocytes. The chains are terminated by di- or trimeric Lewis-x (Lex) determinants, which are also found in tumor-associated carbohydrate antigens in many adenocarcinomas.
Lipopolysaccharide, antigen, LPS, oligosaccharide, structure, core, strain, O-antigen, O antigen, chain, type, core oligosaccharide, region, Helicobacter pylori, Helicobacter
NCBI PubMed ID: 8652593Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Microbiology, University College, Galway, Ireland, Department of Chemistry, York University, North York, Toronto, Ontario M3J 1P3, Canada, Carbohydrate Research Centre, Department of Molecular and Medical Genetics, University of Toronto, Toronto, Ontario M5S 1A8, Canada
Methods: NMR-2D, methylation, FAB-MS, GC-MS, SDS-PAGE, Smith degradation, enzymatic degradation, GPC
Expand this compound
Collapse this compound
5. Compound ID: 1901
Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 614
Aspinall GO, Monteiro MA, Shaver RT, Kurjanczyk LA, Penner JL "Lipopolysaccharides of Helicobacter pylori serogroups O:3 and O:6. Structures of a class of lipopolysaccharides with reference to the location of oligomeric units of D-glycero-a-D-manno-heptose residues" -
European Journal of Biochemistry 248 (1997) 592-601
Lipopolysaccharides (LPS) from antigenically different strains assigned to serogroups O:3 and O:6 of Helicobacter pylori were isolated as water-soluble material of high Mr and as water-insoluble gels of low M,. Chemical and spectroscopic analyses of the soluble LPS and oligosaccharides liberated from the water-insoluble gels led to proposed structures with Lewis (Le) antigen determinants terminating regular repeating units of different types, linked in turn to inner core regions of invariable structure. The O:6 LPS has two populations of related molecules with chains of 3-linked D-glycero-a-D-manno-heptose residues similar to those in the MO19 strain, one with and the other without a single terminal Lewis (LeY') epitope. In contrast, in the O:3 LPS, Lewis (LeX and LeY) epitopes terminate a partially fucosylated N-acetyllactosaminoglycan, but a heptan chain similar to that in the O:6 LPS was shown to connect the outer chains to the inner core. These LPS provide examples of the molecular mimicry of cell-surface glycoconjugates. Structural variations of LPS between strains, and differences in some aspects of structure within strains, between high Mr and low Mr LPS indicate a class of LPS whose mechanisms of biosynthesis lead to overall architectures different from those characteristic of most LPS from enteric bacteria.
Lipopolysaccharide, LPS, core, O-antigen, core oligosaccharide, molecular mimicry, Helicobacter pylori, D-glycero-D-manno-heptose, Helicobacter, molecular mimicry.
NCBI PubMed ID: 9346320Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, York University, Toronto, Ontario, Canada, Depanment of Chemistry, York University, Toronto, Ontario, Canada, Department of Microbiology, University of Toronto, Ontario, Canada
Methods: FAB-MS
Expand this compound
Collapse this compound
6. Compound ID: 1902
|
a-L-Fucp-(1-3)-+
|
?%a-L-Fucp-(1-2)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1--/LPS/ |
Show graphically |
Structure type: oligomer
Aglycon: LPS
Contained glycoepitopes: IEDB_130644,IEDB_130646,IEDB_130654,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_143250,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149555,IEDB_149557,IEDB_149561,IEDB_150092,IEDB_150787,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_158546,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461719,IEDB_461720,IEDB_461721,SB_147,SB_154,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_34,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 614
Aspinall GO, Monteiro MA, Shaver RT, Kurjanczyk LA, Penner JL "Lipopolysaccharides of Helicobacter pylori serogroups O:3 and O:6. Structures of a class of lipopolysaccharides with reference to the location of oligomeric units of D-glycero-a-D-manno-heptose residues" -
European Journal of Biochemistry 248 (1997) 592-601
Lipopolysaccharides (LPS) from antigenically different strains assigned to serogroups O:3 and O:6 of Helicobacter pylori were isolated as water-soluble material of high Mr and as water-insoluble gels of low M,. Chemical and spectroscopic analyses of the soluble LPS and oligosaccharides liberated from the water-insoluble gels led to proposed structures with Lewis (Le) antigen determinants terminating regular repeating units of different types, linked in turn to inner core regions of invariable structure. The O:6 LPS has two populations of related molecules with chains of 3-linked D-glycero-a-D-manno-heptose residues similar to those in the MO19 strain, one with and the other without a single terminal Lewis (LeY') epitope. In contrast, in the O:3 LPS, Lewis (LeX and LeY) epitopes terminate a partially fucosylated N-acetyllactosaminoglycan, but a heptan chain similar to that in the O:6 LPS was shown to connect the outer chains to the inner core. These LPS provide examples of the molecular mimicry of cell-surface glycoconjugates. Structural variations of LPS between strains, and differences in some aspects of structure within strains, between high Mr and low Mr LPS indicate a class of LPS whose mechanisms of biosynthesis lead to overall architectures different from those characteristic of most LPS from enteric bacteria.
Lipopolysaccharide, LPS, core, O-antigen, core oligosaccharide, molecular mimicry, Helicobacter pylori, D-glycero-D-manno-heptose, Helicobacter, molecular mimicry.
NCBI PubMed ID: 9346320Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, York University, Toronto, Ontario, Canada, Depanment of Chemistry, York University, Toronto, Ontario, Canada, Department of Microbiology, University of Toronto, Ontario, Canada
Methods: FAB-MS
Expand this compound
Collapse this compound
7. Compound ID: 1940
|
a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+
| |
b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-D-Gal-ol-(?--/D-Gal-ol-1-d/ |
Show graphically |
Structure type: oligomer
; 1759 [M+H]+
Aglycon: D-Gal-ol-1-d
Contained glycoepitopes: IEDB_114704,IEDB_130646,IEDB_130654,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 612
Aspinall GO, Monteiro MA, Pang H, Walsh EJ, Moran AP "Lipopolysaccharide of the Helicobacter pylori type strain NCTC11637 (ATCC43504): Structure of the O antigen chain and core oligosaccharide regions" -
Biochemistry 35 (1996) 2489-2497
Smooth- and rough-form lipopolysaccharides from phenol-water extraction of cells from Helicobacter pylori type strain NCTC11637 were isolated as the water-soluble component of high-Mr and water-insoluble low-Mr gel. Structural investigations were performed on the intact water-soluble smooth-form lipopolysaccharide, various oligosaccharides formed as chemical and enzymic degradation products, and three oligosaccharide fractions liberated by acetic acid hydrolysis from the water-insoluble rough-form lipopolysaccharide. A structure is proposed for the complete polysaccharide component of the smooth-form lipopolysaccharide comprising the O antigen chain, an intervening region, and the inner core oligosaccharide on the basis of 1H and 13C NMR experiments, fast atom bombardment/mass spectrometry, and methylation linkage analysis of permethylated oligo- and polysaccharide derivatives. The most striking feature of the O antigen region in the lipopolysaccharide is the presence of extended chains with fucosylated and nonfucosylated N-acetyllactosamine (LacNAc) units that mimic human cell surface glycoconjugates in normal human granulocytes. The chains are terminated by di- or trimeric Lewis-x (Lex) determinants, which are also found in tumor-associated carbohydrate antigens in many adenocarcinomas.
Lipopolysaccharide, antigen, LPS, oligosaccharide, structure, core, strain, O-antigen, O antigen, chain, type, core oligosaccharide, region, Helicobacter pylori, Helicobacter
NCBI PubMed ID: 8652593Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Microbiology, University College, Galway, Ireland, Department of Chemistry, York University, North York, Toronto, Ontario M3J 1P3, Canada, Carbohydrate Research Centre, Department of Molecular and Medical Genetics, University of Toronto, Toronto, Ontario M5S 1A8, Canada
Methods: NMR-2D, methylation, FAB-MS, GC-MS, SDS-PAGE, Smith degradation, enzymatic degradation, GPC
Expand this compound
Collapse this compound
8. Compound ID: 1941
|
b-D-Galp-(1-4)-+ a-L-Fucp-(1-3)-+
| |
a-L-Fucp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-D-Gal-ol-(?--/D-Gal-ol-1-d/ |
Show graphically |
Structure type: oligomer
; 1514 [M+H]+
Aglycon: D-Gal-ol-1-d
Contained glycoepitopes: IEDB_114704,IEDB_130646,IEDB_130654,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 612
Aspinall GO, Monteiro MA, Pang H, Walsh EJ, Moran AP "Lipopolysaccharide of the Helicobacter pylori type strain NCTC11637 (ATCC43504): Structure of the O antigen chain and core oligosaccharide regions" -
Biochemistry 35 (1996) 2489-2497
Smooth- and rough-form lipopolysaccharides from phenol-water extraction of cells from Helicobacter pylori type strain NCTC11637 were isolated as the water-soluble component of high-Mr and water-insoluble low-Mr gel. Structural investigations were performed on the intact water-soluble smooth-form lipopolysaccharide, various oligosaccharides formed as chemical and enzymic degradation products, and three oligosaccharide fractions liberated by acetic acid hydrolysis from the water-insoluble rough-form lipopolysaccharide. A structure is proposed for the complete polysaccharide component of the smooth-form lipopolysaccharide comprising the O antigen chain, an intervening region, and the inner core oligosaccharide on the basis of 1H and 13C NMR experiments, fast atom bombardment/mass spectrometry, and methylation linkage analysis of permethylated oligo- and polysaccharide derivatives. The most striking feature of the O antigen region in the lipopolysaccharide is the presence of extended chains with fucosylated and nonfucosylated N-acetyllactosamine (LacNAc) units that mimic human cell surface glycoconjugates in normal human granulocytes. The chains are terminated by di- or trimeric Lewis-x (Lex) determinants, which are also found in tumor-associated carbohydrate antigens in many adenocarcinomas.
Lipopolysaccharide, antigen, LPS, oligosaccharide, structure, core, strain, O-antigen, O antigen, chain, type, core oligosaccharide, region, Helicobacter pylori, Helicobacter
NCBI PubMed ID: 8652593Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Microbiology, University College, Galway, Ireland, Department of Chemistry, York University, North York, Toronto, Ontario M3J 1P3, Canada, Carbohydrate Research Centre, Department of Molecular and Medical Genetics, University of Toronto, Toronto, Ontario M5S 1A8, Canada
Methods: NMR-2D, methylation, FAB-MS, GC-MS, SDS-PAGE, Smith degradation, enzymatic degradation, GPC
Expand this compound
Collapse this compound
9. Compound ID: 1953
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+ | P-7)-+
| | | | | |
a-L-Fucp-(1-2)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(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 |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_130644,IEDB_130646,IEDB_130650,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140088,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_143250,IEDB_144556,IEDB_144562,IEDB_144998,IEDB_145669,IEDB_146664,IEDB_147455,IEDB_149555,IEDB_149557,IEDB_149561,IEDB_150092,IEDB_150787,IEDB_150939,IEDB_150948,IEDB_151531,IEDB_152214,IEDB_153553,IEDB_158546,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_2189046,IEDB_2189047,IEDB_461719,IEDB_461720,IEDB_461721,IEDB_952752,IEDB_983931,SB_147,SB_154,SB_157,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_34,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 613
Aspinall GO, Monteiro MA "Lipopolysaccharides of Helicobacter pylori strains P466 and MO19: Structures of the O antigen and core oligosaccharide regions" -
Biochemistry 35 (1996) 2498-2504
Lipopolysaccharides (LPS) from phenol-water extraction of dyspeptic (P466) and asymptomatic (MO19) strains of Helicobacter pylori were each isolated as water-soluble material of high relative molecular mass (high Mr) and as water-insoluble gels of low Mr. Chemical and spectroscopic analyses of the soluble LPS and oligosaccharides liberated from the water-insoluble gels led to proposed structures for chains comprising the O antigen, intervening, and core regions. As in the LPS from the type strain NCTC11637 [Aspinall, G. O., et al. (1996) Biochemistry 35, 000], the O antigen region of the P466 LPS is characterized by the presence of extended chains with fucosylated and nonfucosylated N-acetyllactosamine units, the former carrying a-L-fucopyranose units at O-3 of b-D-GlcNAc residues. This structure differs from that of the type strain in termination of the O chain by a Lewisy (Ley) antigenic determinant [a-LFuc(1-2)b-D-Gal(1-4)[a-L-Fuc(1-3)]b-D-GlcNAc] but also has internal Lewisx (Lex) units. The inner core region of the P466 LPS is indistinguishable from that in the type strain. In contrast, the O antigen region of the LPS from strain MO19 consists of a single Ley epitope linked via a 3-linked b-D-Gal to an intervening region on the basis of a sequence of 3-linked D-glycero-a-D-manno-heptose residues which is in turn linked to an inner core identical to that in the type strain and the P466 strain. Results in this and the preceding paper show that LPS from the three H. pylori strains display molecular mimicry of human cell surface glycoconjugates but may vary in the expression of Lex or Ley determinants, the degree of O antigen chain extension, or in the presence of an additional region between the inner core and the O antigen.
Lipopolysaccharide, antigen, lipopolysaccharides, LPS, oligosaccharide, structure, core, strain, O-antigen, O antigen, core oligosaccharide, region, Helicobacter pylori, Helicobacter
NCBI PubMed ID: 8652594Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Chemistry, York University, North York, Toronto, Ontario M3J 1P3, Canada
Methods: NMR-2D, defucosylation
Expand this compound
Collapse this compound
10. Compound ID: 2519
Structure type: polymer chemical repeating unit
Trivial name: fucosylated poly(N-acetyl-b-lactosamine), Lewis X antigen determinant, Lewis Y antigen determinant, fucosylated N-acetyllactosaminoglycan, Le (x) trisaccharide repeat
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 858
Knirel YA, Kocharova NA, Hynes SO, Widmalm G, Andersen LP, Jansson P, Moran AP "Structural stuidies on lipopolysaccharides of serologically non-typable strains of Helicobacter pylori, AFI and 007, expressing Lewis antigenic determinants" -
European Journal of Biochemistry 266(1) (1999) 123-131
In contrast to other Helicobacter pylori strains, which have serologically detectable Lewis(x)+ (Le(x)) and Lewis(y)++ (++Le(y)) antigenic determinants in the O-specific polysaccharide chains of the lipopolysaccharides, H. pylori AF1 and 007 were non-typable with anti-Le(x) and anti-Le(y) antibodies. The carbohydrate portions of the lipopolysaccharides were liberated by mild acid hydrolysis and subsequently studied by sugar and methylation analyses, 1H NMR spectroscopy and electrospray ionization-mass spectrometry. Compared with each other, and with lipopolysaccharides of strains studied previously, the lipopolysaccharides of both AF1 and 007 showed similarities, but also differences, in the structures of the core region and O-specific polysaccharide chains. The O-specific polysaccharide chains of both strains consisted of a short or long polyfucosylated poly-N-acetyl-β-lactosamine chains, which were distinguished from those of other strains by a high degree of fucosylation producing a polymeric Le(x)chain terminating with Le(x) or Le(y) units:[sequence: see text] where n = 0 or 1 in strain AF1 and 0 in strain 007, m = 0-2, 6-7 in strain AF1 and m = 0-2, 6-7 or approximately 40 in strain 007, the medium-size species being predominant. Therefore, compared with other strains, the lack of reactivity of lipopolysaccharide of H. pylori AF1 and 007 with anti-Le(x) and anti-Le(y) may reflect the presence of a polymeric Le(x) chain and has important implications for serological and pathogenesis studies. As the substitution pattern of a D-glycero-D-manno-heptose residue in the outer core varied in the two strains, and an extended DD-heptan chain was present in some lipopolysaccharide species but not in others, this region was less conservative than the inner core region. The inner core L-glycero-D-manno-heptose region of both strains carried a 2-aminoethyl phosphate group, rather than a phosphate group, as reported previously for other H. pylori strains.
Lipopolysaccharide, O-antigen, core oligosaccharide, O-specific polysaccharide, Helicobacter pylori
NCBI PubMed ID: 10542057Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: Clinical Research Centre, Huddinge Hospital, Huddinge, Sweden
Methods: methylation, NMR, ESI-MS
- Article ID: 1004
Monteiro MA, Rasko D, Taylor DE, Perry MB "Glucosylated N-acetyllactosamine O-antigen chain in the lipopolysaccharide from Helicobacter pylori strain UA861" -
Glycobiology 8(1) (1998) 107-112
The O-antigen chain from the lipopolysaccharide of Helicobacter pylori strain UA861 was determined to be composed of an elongated type 2 N -acetyllactosamine backbone, -[→3)-β-D-Gal-(1→4)-β-D-GlcNAc-(1-]n→, with approximately half of the GlcNAc units carrying a terminal α-d-Glc residue at the O -6 position. The O-chain of H.pylori UA861 was terminated by a N -acetyllactosamine [β-D-Gal-(1→4)-β-D-GlcNAc] (LacNAc) epitope and did not express terminal Lewis X or Lewis Y blood-group determinants as previously found in other H.pylori strains. The absence of terminal Lewis X and Lewis Y blood-group epitopes and the replacement of Fuc by Glc as a side chain in the O-chain of H.pylori UA861 represents yet another type of lipopolysaccharide structure from H.pylori species. These structural differences in H.pylori lipopolysaccharide molecules carry implications with regard to possible different pathogenic events between strains and respective hosts.
Lipopolysaccharide, Helicobacter pylori, Structure determination, LacNAc
NCBI PubMed ID: 9451019Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR
- Article ID: 1008
Moran AP, Knirel YA, Senchenkova SN, Widmalm G, Hynes SO, Jansson P "Phenotypic variation in molecular mimicry between Helicobacter pylori lipopolysaccharides and human gastric epithelial cell surface glycoforms. Acid-induced phase variation in Lewisx and Lewisy expression by H. pylori lipopolysaccharides" -
Journal of Biological Chemistry 277(8) (2002) 5785-5795
Helicobacter pylori is an important gastroduodenal pathogen of humans whose survival in the gastric environment below pH 4 is dependent on bacterial production of urease, whereas above pH 4 urease-independent mechanisms are involved in survival, but that remain to be elucidated fully. Previous structural investigations on the lipopolysaccharides (LPSs) of H. pylori have shown that the majority of these surface glycolipids express partially fucosylated, glucosylated, or galactosylated N-acetyllactosamine (LacNAc) O-polysaccharide chains containing Lewis(x) (Le(x)) and/or Lewis(y) (Le(y)), although some strains also express type 1 determinants, Lewis(a), Lewis(b), and H-1 antigen. In this study, we investigated acid-induced changes in the structure and composition of LPS and cellular lipids of the genome-sequenced strain, H. pylori 26695. When grown in liquid medium at pH 7, the O-chain consisted of a type 2 LacNAc polysaccharide, which was glycosylated with α-1-fucose at O-3 of the majority of N-acetylglucosamine residues forming Le(x) units, including chain termination by a Le(x) unit. However, growth in liquid medium at pH 5 resulted in production of a more complex O-chain whose backbone of type 2 LacNAc units was partially glycosylated with α-L-fucose, thus forming Le(x), whereas the majority of the nonfucosylated N-acetylglucosamine residues were substituted at O-6 by α-D-galactose residues, and the chain was terminated by a Le(y) unit. In contrast, detailed chemical analysis of the core and lipid A components of LPS and analysis of cellular lipids did not show significant differences between H. pylori 26695 grown at pH 5 and 7. Although putative molecular mechanisms affecting Le(x) and Le(y) expression have been investigated previously, this is the first report identifying an environmental trigger inducing phase variation of Le(x) and Le(y) in H. pylori that can aid adaptation of the bacterium to its ecological niche.
Lipopolysaccharide, structure, Phase variation, phenotype, O-antigen, Helicobacter pylori, Lewis x, blood group antigens, Lewis y
NCBI PubMed ID: 11741906Publication DOI: 10.1074/jbc.M108574200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: pererik.jansson@kfc.hs.sll.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Microbiology, National University of Ireland, Galway, Ireland, Karolinska Institute, Clinical Research Centre, Huddinge University Hospital, Huddinge, Sweden
Methods: methylation, NMR, ESI-MS
- Article ID: 1357
Appelmelk BJ, Martin SL, Monteiro MA, Clayton CA, McColm AA, Zheng PY, Verboom T, Maaskant JJ, van den Eijnden DH, Hokke CH, Perry MB, Vandenbroucke-Grauls CMJE, Kusters JG "Phase variation in Helicobacter pylori lipopolysaccharide due to changes in the lengths of poly(C) tracts in a3- fucosyltransferase genes" -
Infection and Immunity 67(10) (1999) 5361-5366
The lipopolysaccharide (LPS) of Helicobacter pylori expresses the Lewis x (Lex) and/or Ley antigen. We have shown previously that H. pylori LPS displays phase variation whereby an Lex-positive strain yields variants with different LPS serotypes, for example, Lex plus Ley or nonfucosylated polylactosamine. H. pylori has two α3-fucosyltransferase genes that both contain poly(C) tracts. We now demonstrate that these tracts can shorten or lengthen randomly, which results in reversible frameshifting and inactivation of the gene products. We provide genetic and serological evidence that this mechanism causes H. pylori LPS phase variation and demonstrate that the on or off status of α3-fucosyltransferase genes determines the LPS serotypes of phase variants and clinical isolates. The role of the α3-fucosyltransferase gene products in determining the LPS serotype was confirmed by structural-chemical analysis of α3-fucosyltransferase knockout mutants. The data also show that the two α3-fucosyltransferase genes code for enzymes with different fine specificities, and we propose the names futA and futB to designate the orthologs of the H. pylori 26695 α3-fucosyltransferase genes HP0379 and HP0651, respectively. The data also show that the α3-fucosylation precedes α2-fucosylation [corrected], an order of events opposite to that which prevails in mammals. Finally, the data provide an understanding at the molecular level of the mechanisms underlying LPS diversity in H. pylori, which may play an important role in adaptation to the host.
Lipopolysaccharide, Phase variation, gene, variation, Helicobacter pylori, Helicobacter, fucosyltransferase
NCBI PubMed ID: 10496917Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Med.School, Amsterdam, The Netherlands
- Article ID: 3300
Aspinall GO, Monteiro MA, Pang H, Walsh EJ, Moran AP "O antigen chains in the lipopolysaccharide of Helicobacter pylori NCTC 11637" -
Carbohydrate Letters 1 (1994) 151-156
The O antigen region in the lipopolysaccharide of the smoothform of Helicobacter pylori NCTC 11637 has been shown to contain partially fucosylated N-acetyllactosaminoglycan chains terminated by the Lex determinant that mimic human cell surface glycoconjugates.
Lipopolysaccharide, antigen, LPS, polysaccharide, O-antigen, O antigen, chain, FAB MS, Helicobacter pylori, Helicobacter, structure determinayion, N-acetyllactosaminoglycan, Lex determinant
Journal NLM ID: 9607448Publisher: Harwood Academic Publishers; Basel; Langhorne, PA: International Publishers Distributor
Institutions: Department of Chemistry, York University, North York, Ontario, CANADA
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, mild acid hydrolysis, Smith degradation, composition analysis
- Article ID: 3367
Moran AP "Lipopolysaccharide in bacterial chronic infection: Insights from Helicobacter pylori lipopolysaccharide and lipid A" -
International Journal of Medical Microbiology 297(5) (2007) 307-319
Lipopolysaccharides are generally considered toxic components of the Gram-negative bacterial outer membrane with potent immunomodulating and immunostimulating properties, but their contribution to adaptation of a given bacterial species to its microbial niche is, however, predominantly overlooked. Helicobacter pylori, as a cause of long-term infection in the gastroduodenal tract, has been proposed as a model for investigating and understanding the dynamics of bacterial persistence and parasitism in chronic infections. This review examines the structure and properties of H. pylori lipopolysaccharide and its lipid A moiety, and the insights that have been gained into their contribution to chronic infection and pathogenesis, including evasion and dampening of innate immune responses
lipid A, Helicobacter pylori, toll-like receptors, Lipopolysccharide, Lewis antigens, Innate immune response
NCBI PubMed ID: 17467335Journal NLM ID: 100898849Publisher: Jena, Germany: Urban & Fischer Verlag
Correspondence: anthony.moran@nuigalway.ie
Institutions: Department of Microbiology, National University of Ireland, Galway, University Road, Galway, Ireland
- Article ID: 3422
Chandan V, Logan SM, Harrison BA, Vinogradov E, Aubry A, Stupak J, Li J, Altman E "Characterization of a waaF mutant of Helicobacter pylori strain 26695 provides evidence that an extended lipopolysaccharide structure has a limited role in the invasion of gastric cancer cells" -
Biochemistry and Cell Biology 85(5) (2007) 582-590
An LD-heptosyltransferase gene, HP1191 (waaF), involved in biosynthesis of the inner-core region of Helicobacter pylori strain 26695 lipopolysaccharide (LPS), has been cloned and its function established by complementation of Salmonella enterica serovar Typhimurium waaF mutant strain, strain 3789. Insertional inactivation of the HP1191 open reading frame in strain 26695 resulted in the formation of a deeply truncated LPS molecule, as observed using SDS-PAGE. Subsequent compositional and fatty acid analyses, followed by capillary electrophoresis - mass spectrometry and nuclear magnetic resonance studies established its structure as the following: PE→7)-L-α-D-Hepp-(1→5)-α-Kdop-(2→6)-Lipid A, where PE represents a phosphoethanolamine group, LD-Hep represents L-glycero-D-manno-heptose, and Kdo represents 3-deoxy-D-manno-oct-2-ulosonic acid. This structural analysis identifies the activity of HP1191 as a heptosyltransferase and a waaF homolog. In vitro invasion assays using human cultured gastric adenocarcinoma cells as a host cell model confirmed that the level of invasion was unaffected for an H. pylori HP1191::Kan deep-rough mutant strain compared with the wild-type strain 26695 expressing the O-chain polysaccharide, providing evidence that LPS is not a critical factor for invasion.
Lipopolysaccharide, Helicobacter pylori, heptosyl transferase, invasion
NCBI PubMed ID: 17901900Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: Eleonora.altman@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, ON, K1A 0R6, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GLC-MS, HF solvolysis, sugar analysis, 31P NMR, genetic methods, alkaline hydrolysis, CE-MS
Expand this compound
Collapse this compound
11. Compound ID: 2856
|
b-D-Galp-(1-4)-+ a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ EtN-(1--P--7)--+
| | |
a-L-Fucp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(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_130646,IEDB_130650,IEDB_130654,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140088,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_145669,IEDB_146664,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_2189046,IEDB_2189047,IEDB_461720,IEDB_983931,SB_157,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,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
12. Compound ID: 2857
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
b-D-Galp-(1-4)-+ a-L-Fucp-(1-3)-+ | EtN-(1--P--7)--+
| | | |
a-L-Fucp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(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_130646,IEDB_130650,IEDB_130654,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140088,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_144998,IEDB_145669,IEDB_146664,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_2189046,IEDB_2189047,IEDB_461720,IEDB_952752,IEDB_983931,SB_157,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,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
13. Compound ID: 2872
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,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
Expand this compound
Collapse this compound
14. Compound ID: 2882
|
a-L-Fucp-(1-3)-+
|
-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-
|
a-D-Galp-(1-6)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151528,IEDB_151531,IEDB_152214,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1008
Moran AP, Knirel YA, Senchenkova SN, Widmalm G, Hynes SO, Jansson P "Phenotypic variation in molecular mimicry between Helicobacter pylori lipopolysaccharides and human gastric epithelial cell surface glycoforms. Acid-induced phase variation in Lewisx and Lewisy expression by H. pylori lipopolysaccharides" -
Journal of Biological Chemistry 277(8) (2002) 5785-5795
Helicobacter pylori is an important gastroduodenal pathogen of humans whose survival in the gastric environment below pH 4 is dependent on bacterial production of urease, whereas above pH 4 urease-independent mechanisms are involved in survival, but that remain to be elucidated fully. Previous structural investigations on the lipopolysaccharides (LPSs) of H. pylori have shown that the majority of these surface glycolipids express partially fucosylated, glucosylated, or galactosylated N-acetyllactosamine (LacNAc) O-polysaccharide chains containing Lewis(x) (Le(x)) and/or Lewis(y) (Le(y)), although some strains also express type 1 determinants, Lewis(a), Lewis(b), and H-1 antigen. In this study, we investigated acid-induced changes in the structure and composition of LPS and cellular lipids of the genome-sequenced strain, H. pylori 26695. When grown in liquid medium at pH 7, the O-chain consisted of a type 2 LacNAc polysaccharide, which was glycosylated with α-1-fucose at O-3 of the majority of N-acetylglucosamine residues forming Le(x) units, including chain termination by a Le(x) unit. However, growth in liquid medium at pH 5 resulted in production of a more complex O-chain whose backbone of type 2 LacNAc units was partially glycosylated with α-L-fucose, thus forming Le(x), whereas the majority of the nonfucosylated N-acetylglucosamine residues were substituted at O-6 by α-D-galactose residues, and the chain was terminated by a Le(y) unit. In contrast, detailed chemical analysis of the core and lipid A components of LPS and analysis of cellular lipids did not show significant differences between H. pylori 26695 grown at pH 5 and 7. Although putative molecular mechanisms affecting Le(x) and Le(y) expression have been investigated previously, this is the first report identifying an environmental trigger inducing phase variation of Le(x) and Le(y) in H. pylori that can aid adaptation of the bacterium to its ecological niche.
Lipopolysaccharide, structure, Phase variation, phenotype, O-antigen, Helicobacter pylori, Lewis x, blood group antigens, Lewis y
NCBI PubMed ID: 11741906Publication DOI: 10.1074/jbc.M108574200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: pererik.jansson@kfc.hs.sll.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Microbiology, National University of Ireland, Galway, Ireland, Karolinska Institute, Clinical Research Centre, Huddinge University Hospital, Huddinge, Sweden
Methods: methylation, NMR, ESI-MS
Expand this compound
Collapse this compound
15. Compound ID: 3620
|
b-D-Galp-(1-4)-+ a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+ a-L-Fucp-(1-3)-+
| | | |
a-L-Fucp-(1-3)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-GlcpNAc-(1--/core-lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: core-lipid A
Contained glycoepitopes: IEDB_130646,IEDB_130654,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141500,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144556,IEDB_144562,IEDB_145669,IEDB_147455,IEDB_149557,IEDB_150092,IEDB_150939,IEDB_151531,IEDB_152214,IEDB_158550,IEDB_174333,IEDB_190606,IEDB_2151203,IEDB_461720,IEDB_952752,SB_157,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1356
Appelmelk BJ, Shiberu B, Trinks C, Tapsi N, Zheng PY, Verboom T, Maaskant J, Hokke CH, Schiphorst WECM, Blanchard D, Simoons-Smit IM, van den Eijnden DH, Vandenbroucke-Grauls CMJE "Phase variation in Helicobacter pylori lipopolysaccharide" -
Infection and Immunity 66(1) (1998) 70-76
Lipopolysaccharide, LPS, Phase variation, phase, variation, O-antigen, Helicobacter pylori, Helicobacter, Lewis x, Lewis y
Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: BJ.Appelmelk.mm@med.vu.nl
Institutions: Department of Medical Microbiology, Vrije Universiteit, Medical School, Amterdam, The Netherlands
Expand this compound
Collapse this compound
Next 15 structure(s)
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (record IDs):
Execution: 8 sec