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 paperNCBI PubMed ID: 21790998Publication DOI: 10.1111/j.1742-4658.2011.08270.xJournal NLM ID: 101229646Publisher: 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, OS3
Contained glycoepitopes: IEDB_136044,IEDB_136045,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149136,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_2189046,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: Product of deamination of PS1 and OS1. -2)bDRibf(1- chain may be one or two residues longer
Related record ID(s): 26128, 26543, 26544, 26545, 26546, 26547, 26548, 26549, 26551, 26552, 26553, 26554, 26555, 26556, 26557
NCBI Taxonomy refs (TaxIDs): 102617Reference(s) to other database(s): GTC:G55629LJ
Show glycosyltransferases
NMR conditions: at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7
3,3,7,3,4,2,2,2 bDRibf 109.2 75.7 71.9 84.1 64.0
3,3,7,3,4,2,2 bDRibf 107.7 82.2 71.5 84.4 64.0
3,3,7,3,4,2 bDRibf 107.7 82.2 71.5 84.4 64.0
3,3,7,3,4 bDRibf 108.3 82.4 71.2 83.9 64.0
3,3,7,3 bDGalp 104.6 72.5 74.1 76.9 75.9 62.5
3,3,7 aDGlcp 99.3 72.0 83.4 69.4 72.6 61.8
3,3 aXDDmanHepp 103.5 71.1 71.9 68.3 75.4 70.5 69.1
3 aLFucp 100.0 68.5 78.4 72.7 68.3 16.4
xD2,5anhMan-ol 62.1 82.7 84.6 76.5 83.9 62.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7
3,3,7,3,4,2,2,2 bDRibf 5.20 4.18 4.24 4.04 3.66-3.83
3,3,7,3,4,2,2 bDRibf 5.40 4.21 4.33 4.01 3.66-3.83
3,3,7,3,4,2 bDRibf 5.40 4.21 4.33 4.01 3.66-3.83
3,3,7,3,4 bDRibf 5.49 4.23 4.24 3.98 3.66-3.83
3,3,7,3 bDGalp 4.66 3.59 3.79 4.01 3.75 3.75
3,3,7 aDGlcp 4.97 3.77 3.97 3.55 3.79 3.79-3.87
3,3 aXDDmanHepp 5.07 4.05 3.87 3.75 3.87 4.26 3.76-3.87
3 aLFucp 4.96 3.90 3.97 4.04 4.22 1.21
xD2,5anhMan-ol 3.75 4.08 4.08 4.19 3.94 3.72-3.79
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7
3,3,7,3,4,2,2,2 bDRibf 109.2/5.20 75.7/4.18 71.9/4.24 84.1/4.04 64.0/3.66-3.83
3,3,7,3,4,2,2 bDRibf 107.7/5.40 82.2/4.21 71.5/4.33 84.4/4.01 64.0/3.66-3.83
3,3,7,3,4,2 bDRibf 107.7/5.40 82.2/4.21 71.5/4.33 84.4/4.01 64.0/3.66-3.83
3,3,7,3,4 bDRibf 108.3/5.49 82.4/4.23 71.2/4.24 83.9/3.98 64.0/3.66-3.83
3,3,7,3 bDGalp 104.6/4.66 72.5/3.59 74.1/3.79 76.9/4.01 75.9/3.75 62.5/3.75
3,3,7 aDGlcp 99.3/4.97 72.0/3.77 83.4/3.97 69.4/3.55 72.6/3.79 61.8/3.79-3.87
3,3 aXDDmanHepp 103.5/5.07 71.1/4.05 71.9/3.87 68.3/3.75 75.4/3.87 70.5/4.26 69.1/3.76-3.87
3 aLFucp 100.0/4.96 68.5/3.90 78.4/3.97 72.7/4.04 68.3/4.22 16.4/1.21
xD2,5anhMan-ol 62.1/3.75 82.7/4.08 84.6/4.08 76.5/4.19 83.9/3.94 62.0/3.72-3.79
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 |
|---|
| 3,3,7,3,4,2,2,2 | bDRibf | 5.20 | 4.18 | 4.24 | 4.04 | 3.66
3.83 | |
| 3,3,7,3,4,2,2 | bDRibf | 5.40 | 4.21 | 4.33 | 4.01 | 3.66
3.83 | |
| 3,3,7,3,4,2 | bDRibf | 5.40 | 4.21 | 4.33 | 4.01 | 3.66
3.83 | |
| 3,3,7,3,4 | bDRibf | 5.49 | 4.23 | 4.24 | 3.98 | 3.66
3.83 | |
| 3,3,7,3 | bDGalp | 4.66 | 3.59 | 3.79 | 4.01 | 3.75 | 3.75 | |
| 3,3,7 | aDGlcp | 4.97 | 3.77 | 3.97 | 3.55 | 3.79 | 3.79
3.87 | |
| 3,3 | aXDDmanHepp | 5.07 | 4.05 | 3.87 | 3.75 | 3.87 | 4.26 | 3.76
3.87 |
| 3 | aLFucp | 4.96 | 3.90 | 3.97 | 4.04 | 4.22 | 1.21 | |
| | xD2,5anhMan-ol | 3.75 | 4.08 | 4.08 | 4.19 | 3.94 | 3.72
3.79 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 |
|---|
| 3,3,7,3,4,2,2,2 | bDRibf | 109.2 | 75.7 | 71.9 | 84.1 | 64.0 | |
| 3,3,7,3,4,2,2 | bDRibf | 107.7 | 82.2 | 71.5 | 84.4 | 64.0 | |
| 3,3,7,3,4,2 | bDRibf | 107.7 | 82.2 | 71.5 | 84.4 | 64.0 | |
| 3,3,7,3,4 | bDRibf | 108.3 | 82.4 | 71.2 | 83.9 | 64.0 | |
| 3,3,7,3 | bDGalp | 104.6 | 72.5 | 74.1 | 76.9 | 75.9 | 62.5 | |
| 3,3,7 | aDGlcp | 99.3 | 72.0 | 83.4 | 69.4 | 72.6 | 61.8 | |
| 3,3 | aXDDmanHepp | 103.5 | 71.1 | 71.9 | 68.3 | 75.4 | 70.5 | 69.1 |
| 3 | aLFucp | 100.0 | 68.5 | 78.4 | 72.7 | 68.3 | 16.4 | |
| | xD2,5anhMan-ol | 62.1 | 82.7 | 84.6 | 76.5 | 83.9 | 62.0 | |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
