Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: hemolytic-uremic syndrome (HUS) [ICD11:
3A21.2 
];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 25665776Publication DOI: 10.1016/j.carres.2014.11.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru (A.V. Perepelov)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China.
An acidic O-polysaccharide (O-antigen) of Escherichia coli O163 was obtained by mild acid hydrolysis of the lipopolysaccharide and studied by sugar analysis and Smith degradation along with 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure of the linear tetrasaccharide repeating unit was established, which is unique among known structures of bacterial polysaccharides: →2)-β-D-Manp-(1→4)-β-D-GlcpA-(1→3)-α-L-QuipNAc-(1→3)-α-D-GlcpNAc-(1→. Functions of genes in the O-antigen gene cluster of E. coli O163 were tentatively assigned by comparison with sequences in the available databases and found to be in agreement with the O-polysaccharide structure. Relationships between O-antigen structures and gene clusters of E. coli O163 and Salmonella enterica O41 are discussed.
Lipopolysaccharide, O-antigen, Escherichia coli, bacterial polysaccharide structure, O-antigen gene cluster
Structure type: oligomer
Location inside paper: p.35, fig.1
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, sugar analysis, DNA techniques, GLC, mild acid hydrolysis, Smith degradation, NMR-1D, GPC, function analysis of gene clusters
Biosynthesis and genetic data: genetic data
Comments, role: Oligosaccharide derived by Smith degradation of the OPS. Subst = destruction product from 2-substituted Man
Related record ID(s): 30649
NCBI Taxonomy refs (TaxIDs): 2100520
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,3,2 Ac 175.0-175.3 23.1-23.4
3,2,3 aLQuipN 98.3 55.1 71.9 76.5 69.2 17.6
3,2,2 Ac 175.0-175.3 23.1-23.4
3,2 aDGlcpN 98.2 54.8 77.1 69.4 73.6 61.7
3 Subst 103.7 79.6 60.8 62.5-62.6 81.2 62.5-62.6
xDEry-onic 177.3 72.5 81.4 61.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,3,2 Ac - 1.97-2.02
3,2,3 aLQuipN 5.00 3.91 3.65 3.21 4.14 1.27
3,2,2 Ac - 1.97-2.02
3,2 aDGlcpN 5.04 4.08 3.86 3.57 3.90 3.80-3.88
3 Subst 5.11 3.88 3.78-3.90 3.67-3.74 3.92 3.67-3.74
xDEry-onic - 4.44 4.18 3.71-3.76
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,3,2 Ac 23.1-23.4/1.97-2.02
3,2,3 aLQuipN 98.3/5.00 55.1/3.91 71.9/3.65 76.5/3.21 69.2/4.14 17.6/1.27
3,2,2 Ac 23.1-23.4/1.97-2.02
3,2 aDGlcpN 98.2/5.04 54.8/4.08 77.1/3.86 69.4/3.57 73.6/3.90 61.7/3.80-3.88
3 Subst 103.7/5.11 79.6/3.88 60.8/3.78-3.90 62.5-62.6/3.67-3.74 81.2/3.92 62.5-62.6/3.67-3.74
xDEry-onic 72.5/4.44 81.4/4.18 61.6/3.71-3.76
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,3,2 | Ac |
| 1.97
2.02 | |
| 3,2,3 | aLQuipN | 5.00 | 3.91 | 3.65 | 3.21 | 4.14 | 1.27 |
| 3,2,2 | Ac |
| 1.97
2.02 | |
| 3,2 | aDGlcpN | 5.04 | 4.08 | 3.86 | 3.57 | 3.90 | 3.80
3.88 |
| 3 | Subst | 5.11 | 3.88 | 3.78
3.90 | 3.67
3.74 | 3.92 | 3.67
3.74 |
| | xDEry-onic |
| 4.44 | 4.18 | 3.71
3.76 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,3,2 | Ac | 175.0
175.3 | 23.1
23.4 | |
| 3,2,3 | aLQuipN | 98.3 | 55.1 | 71.9 | 76.5 | 69.2 | 17.6 |
| 3,2,2 | Ac | 175.0
175.3 | 23.1
23.4 | |
| 3,2 | aDGlcpN | 98.2 | 54.8 | 77.1 | 69.4 | 73.6 | 61.7 |
| 3 | Subst | 103.7 | 79.6 | 60.8 | 62.5
62.6 | 81.2 | 62.5
62.6 |
| | xDEry-onic | 177.3 | 72.5 | 81.4 | 61.6 | |
|
There is only one chemically distinct structure:
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Found 1 record.
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