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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: chronic gastritis [ICD11: DA42.Z

, ICD11: XT8W

]; peptic ulcer [ICD11: DA61

, ICD11: XN3DY

]; gastric cancer [ICD11: 2B72.Z

]; infection due to Helicobacter pylori [ICD11: XN3DY

]

The structure was elucidated in this paper
NCBI PubMed ID: 21790998
Publication DOI: 10.1111/j.1742-4658.2011.08270.x
Journal NLM ID: 101229646
Publisher: Blackwell Publishing
Correspondence: evguenii.vinogradov

nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council Canada, Ottawa, ON, Canada

In this study, we describe a reinvestigation of the lipopolysaccharide (LPS) structure of Helicobacter pylori strain Sydney (SS1) based on the NMR analysis of oligosaccharides obtained through the use of various degradations of the LPS as well as capillary electrophoresis-MS data. The results of the analysis indicated that the core region of a major H. pylori SS1 LPS glycoform consists of a backbone core oligosaccharide substituted at the d-glycero-d-manno-heptose (dd-Hep) residue by a linear chain composed of a trisaccharide fragment α-ddHep-3-α-L-Fuc-3-β-GlcNAc, as previously demonstrated for H. pylori strain 26695, further elongated by consecutively added α-Glc and β-Gal residues, and terminating in a novel linear chain consisting of 1,2-linked β-ribofuranosyl residues, where the last β-ribofuranosyl residue provides a point of attachment for the O-chain polysaccharide: [Formula: see text] where [2-β-Ribf-](n) is a short (three to five residues) oligomer of 1,2-linked β-ribofuranose (riban), and PS is a polysaccharide chain consisting of N-acetyllactosamine, substituted with α-Fuc to form Lewis (Le)-type structures. In addition to the previously identified LacNAc, Le(y) and Le(x) components, the O-chain polysaccharide of H. pylori SS1 LPS was found to contain a novel LacNAc unit carrying a phosphoethanolamine substituent at the O-6 position of β-GlcNAc residues.

Lipopolysaccharide, NMR, core region, Helicobacter pylori

Structure type: oligomer
Location inside paper: p.3486, fig.1
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136044,IEDB_136045,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_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88

Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, GLC-MS, NMR-2D, sugar analysis, 31P NMR, deacylation, deamination, NMR-1D, CE-MS
Comments, role: Minor product of KOH deacylation of H.pylori SS1 LPS. Lower molecular mass fraction from Sephadex G-50.

Related record ID(s): 26543, 26544, 26545, 26546, 26547, 26548, 26549, 26550, 26551, 26552, 26553, 26554, 26555, 26556, 26557, 26563
NCBI Taxonomy refs (TaxIDs): 102617
Reference(s) to other database(s): GTC:G20924WB
Show glycosyltransferases

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@@H](O)[C@H](O)[C@@H]([C@H](O)CO[C@@H]4O[C@H](CO)[C@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)O[C@@H]3O[C@H]3[C@@H](O)[C@H](O)[C@@H]([C@@H](O)CO)O[C@@H]3O[C@@H]3[C@H](O)[C@@H](O[C@@H]4[C@H](O)C[C@](OC[C@H]5O[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](N)CO)[C@H](N)[C@@H](O)[C@@H]5O)(C(=O)O)O[C@@H]4[C@H](O)CO)O[C@H]([C@@H](O)COP(=O)(O)OCCN)[C@H]3O)[C@@H]2N)[C@@H](O)[C@H](O[C@H]2O[C@H]([C@H](O)CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize