Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 21861990Publication DOI: 10.1016/j.carres.2011.07.021Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
A structure of the O-polysaccharide (O-antigen) of Escherichia coli O158 has been reported (Datta, A. K.; Basu, S.; Roy, N. Carbohydr. Res.1999, 322, 219-227). In this work, we reinvestigated the O158 polysaccharide using sugar analyses, Smith degradation, and (1)H and (13)C NMR spectroscopy and established the following structure, which is at variance with the structure established earlier: [see formula in text]. This structure is in agreement with the predicted functions of genes found in the O-antigen gene cluster of E. coli O158.
O-antigen, Escherichia coli, O-antigen gene cluster, O-Polysaccharide structure
Structure type: polymer chemical repeating unit
Location inside paper: p.2276, fig.2, 2
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885813,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, Smith degradation
Comments, role: O-deacetylated polysaccharide
Related record ID(s): 26309, 26909
NCBI Taxonomy refs (TaxIDs): 2162918Reference(s) to other database(s): GTC:G39922CE
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,2 Ac 175.9 23.5
3,4,3 aLRhap 100.9 71.5 71.5 73.5 70.1 18.0
3,4,6 bDGlcp 103.5 74.3 77.3 71.2 77.5 62.2
3,4 bDManpN 98.1 50.8 75.2 71.7 75.7 68.5
3 aDGalpA 102.1 69.6 70.8 78.8 72.2 174.1
2 Ac 176.7 23.5
bDGlcpN 101.8 56.0 83.3 72.3 77.0 62.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2 Ac - 1.95
3,4,3 aLRhap 4.92 3.75 3.85 3.44 4.24 1.28
3,4,6 bDGlcp 4.59 3.36 3.54 3.41 3.51 3.76-3.96
3,4 bDManpN 4.93 4.66 3.88 3.88 3.45 3.76-4.27
3 aDGalpA 5.26 3.78 3.94 4.46 4.31 -
2 Ac - 2.04
bDGlcpN 4.54 3.75 3.65 3.56 3.42 3.74-3.93
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2 Ac 23.5/1.95
3,4,3 aLRhap 100.9/4.92 71.5/3.75 71.5/3.85 73.5/3.44 70.1/4.24 18.0/1.28
3,4,6 bDGlcp 103.5/4.59 74.3/3.36 77.3/3.54 71.2/3.41 77.5/3.51 62.2/3.76-3.96
3,4 bDManpN 98.1/4.93 50.8/4.66 75.2/3.88 71.7/3.88 75.7/3.45 68.5/3.76-4.27
3 aDGalpA 102.1/5.26 69.6/3.78 70.8/3.94 78.8/4.46 72.2/4.31
2 Ac 23.5/2.04
bDGlcpN 101.8/4.54 56.0/3.75 83.3/3.65 72.3/3.56 77.0/3.42 62.6/3.74-3.93
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2 | Ac |
| 1.95 | |
| 3,4,3 | aLRhap | 4.92 | 3.75 | 3.85 | 3.44 | 4.24 | 1.28 |
| 3,4,6 | bDGlcp | 4.59 | 3.36 | 3.54 | 3.41 | 3.51 | 3.76
3.96 |
| 3,4 | bDManpN | 4.93 | 4.66 | 3.88 | 3.88 | 3.45 | 3.76
4.27 |
| 3 | aDGalpA | 5.26 | 3.78 | 3.94 | 4.46 | 4.31 |
|
| 2 | Ac |
| 2.04 | |
| | bDGlcpN | 4.54 | 3.75 | 3.65 | 3.56 | 3.42 | 3.74
3.93 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2 | Ac | 175.9 | 23.5 | |
| 3,4,3 | aLRhap | 100.9 | 71.5 | 71.5 | 73.5 | 70.1 | 18.0 |
| 3,4,6 | bDGlcp | 103.5 | 74.3 | 77.3 | 71.2 | 77.5 | 62.2 |
| 3,4 | bDManpN | 98.1 | 50.8 | 75.2 | 71.7 | 75.7 | 68.5 |
| 3 | aDGalpA | 102.1 | 69.6 | 70.8 | 78.8 | 72.2 | 174.1 |
| 2 | Ac | 176.7 | 23.5 | |
| | bDGlcpN | 101.8 | 56.0 | 83.3 | 72.3 | 77.0 | 62.6 |
|
There is only one chemically distinct structure:
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