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: polymer chemical repeating unit
Location inside paper: p.3486, fig.1, PS2
Trivial name: O-chain region
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130646,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_150939,IEDB_151531,IEDB_158550,IEDB_190606,SB_165,SB_166,SB_173,SB_187,SB_195,SB_30,SB_7,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: Part of structure (see ID26556). Product of periodate oxidation-reduction-acid hydrolysis of LPS.
Related record ID(s): 26128, 26543, 26544, 26545, 26546, 26547, 26548, 26549, 26550, 26551, 26552, 26553, 26554, 26555, 26556
NCBI Taxonomy refs (TaxIDs): 102617
Show glycosyltransferases
NMR conditions: at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3,4 bDGalp 104.1 71.2 83.4 69.5 76.1 62.2
4,3,2 Ac ? 23.5
4,3 bDGlcpN 103.9 56.3 73.3 79.3 75.7 61.0
4 bDGalp 103.7 71.2 83.4 69.5 76.1 62.2
2 Ac ? 23.5
6,0,2 Me 43.7
6,0 xXEtN 60.6 58.5
6 P
bDGlcpN 103.9 56.3 73.3 78.5 74.4 65.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3,4 bDGalp 4.47 3.58 3.73 4.15 3.72 3.74-3.78
4,3,2 Ac - 2.04
4,3 bDGlcpN 4.71 3.81 3.74 3.73 3.59 3.84-3.95
4 bDGalp 4.53 3.56 3.75 4.15 3.72 3.74-3.78
2 Ac - 2.04
6,0,2 Me 2.96
6,0 xXEtN 4.21 3.45
6 P
bDGlcpN 4.71 3.81 3.74 3.81 3.72 4.21
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3,4 bDGalp 104.1/4.47 71.2/3.58 83.4/3.73 69.5/4.15 76.1/3.72 62.2/3.74-3.78
4,3,2 Ac 23.5/2.04
4,3 bDGlcpN 103.9/4.71 56.3/3.81 73.3/3.74 79.3/3.73 75.7/3.59 61.0/3.84-3.95
4 bDGalp 103.7/4.53 71.2/3.56 83.4/3.75 69.5/4.15 76.1/3.72 62.2/3.74-3.78
2 Ac 23.5/2.04
6,0,2 Me 43.7/2.96
6,0 xXEtN 60.6/4.21 58.5/3.45
6 P
bDGlcpN 103.9/4.71 56.3/3.81 73.3/3.74 78.5/3.81 74.4/3.72 65.1/4.21
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,3,4 | bDGalp | 4.47 | 3.58 | 3.73 | 4.15 | 3.72 | 3.74
3.78 |
| 4,3,2 | Ac |
| 2.04 | |
| 4,3 | bDGlcpN | 4.71 | 3.81 | 3.74 | 3.73 | 3.59 | 3.84
3.95 |
| 4 | bDGalp | 4.53 | 3.56 | 3.75 | 4.15 | 3.72 | 3.74
3.78 |
| 2 | Ac |
| 2.04 | |
| 6,0,2 | Me | 2.96 | |
| 6,0 | xXEtN | 4.21 | 3.45 | |
| 6 | P | |
| | bDGlcpN | 4.71 | 3.81 | 3.74 | 3.81 | 3.72 | 4.21 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3,4 | bDGalp | 104.1 | 71.2 | 83.4 | 69.5 | 76.1 | 62.2 |
| 4,3,2 | Ac | ? | 23.5 | |
| 4,3 | bDGlcpN | 103.9 | 56.3 | 73.3 | 79.3 | 75.7 | 61.0 |
| 4 | bDGalp | 103.7 | 71.2 | 83.4 | 69.5 | 76.1 | 62.2 |
| 2 | Ac | ? | 23.5 | |
| 6,0,2 | Me | 43.7 | |
| 6,0 | xXEtN | 60.6 | 58.5 | |
| 6 | P | |
| | bDGlcpN | 103.9 | 56.3 | 73.3 | 78.5 | 74.4 | 65.1 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":104.1,"l":"1","c":[0,0,225]},{"s":71.2,"l":"2","c":[0,0,225]},{"s":83.4,"l":"3","c":[0,0,225]},{"s":69.5,"l":"4","c":[0,0,225]},{"s":76.1,"l":"5","c":[0,0,225]},{"s":62.2,"l":"6","c":[0,0,225]},{"s":23.5,"l":"2","c":[0,0,0]},{"s":103.9,"l":"1","c":[230,0,30]},{"s":56.3,"l":"2","c":[230,0,30]},{"s":73.3,"l":"3","c":[230,0,30]},{"s":79.3,"l":"4","c":[230,0,30]},{"s":75.7,"l":"5","c":[230,0,30]},{"s":61,"l":"6","c":[230,0,30]},{"s":103.7,"l":"1","c":[0,165,0]},{"s":71.2,"l":"2","c":[0,165,0]},{"s":83.4,"l":"3","c":[0,165,0]},{"s":69.5,"l":"4","c":[0,165,0]},{"s":76.1,"l":"5","c":[0,165,0]},{"s":62.2,"l":"6","c":[0,165,0]},{"s":23.5,"l":"2","c":[0,0,0]},{"s":43.7,"l":"1","c":[0,0,0]},{"s":60.6,"l":"1","c":[120,0,225]},{"s":58.5,"l":"2","c":[120,0,225]},{"s":103.9,"l":"1","c":[0,192,255]},{"s":56.3,"l":"2","c":[0,192,255]},{"s":73.3,"l":"3","c":[0,192,255]},{"s":78.5,"l":"4","c":[0,192,255]},{"s":74.4,"l":"5","c":[0,192,255]},{"s":65.1,"l":"6","c":[0,192,255]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
