Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 20546712Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Perepelov <perepel
ioc.ac.ru>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
O-Polysaccharides (O-antigens) were isolated from Escherichia coli O13, O129, and O135 and studied by chemical analyses along with 2D (1)H and (13)C NMR spectroscopy. They were found to possess a common →2)-l-Rha-(α1→2)-l-Rha-(α1→3)-l-Rha-(α1→3)-d-GlcNAc-(β1→ backbone, which is a characteristic structural motif of the O-polysaccharides of Shigella flexneri types 1-5. In both the bacterial species, the backbone is decorated with lateral glucose residues or/and O-acetyl groups. In E. coli O13, a new site of glycosylation on 3-substituted Rha was revealed and the following O-polysaccharide structure was established: The structure of the E. coli O129 antigen was found to be identical to the O-antigen structure of S. flexneri type 5a specified in this work and that of E. coli O135 to S. flexneri type 4b reported earlier.
O-antigen, Escherichia coli, Shigella flexneri, O-acetylation, bacterial polysaccharide structure, Glucosylation site
Structure type: suggested polymer biological repeating unit
Location inside paper: table 1, p.1597, chart 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, de-O-acetylation
Comments, role: O-deacetylated O-PS; Escherichia coli O13 strain G1237
Related record ID(s): 11565, 25391, 25804, 25805, 28868, 30445
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G58114KG
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2 aLRhap 102.5 80.1 71.2 73.7 70.6 18.1
3,3 aLRhap 101.8 79.3 71.5 73.5 70.6 18.1
3,2 aDGlcp 98.7 72.8 74.1 70.7 73.5 61.9
3 aLRhap 99.2 77.3 75.8 73.7 70.9 17.6
2 Ac 175.8 23.9
bDGlcpN 103.6 57.1 83.0 69.7 77.3 62.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2 aLRhap 5.14 4.15 3.88 3.32 3.67 1.25
3,3 aLRhap 5.27 4.05 3.82 3.49 3.69 1.33
3,2 aDGlcp 4.92 3.54 3.78 3.52 3.83 3.82-3.85
3 aLRhap 5.05 3.86 3.96 3.71 4.02 1.26
2 Ac - 2.08
bDGlcpN 4.73 3.84 3.65 3.55 3.46 3.76-3.91
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2 aLRhap 102.5/5.14 80.1/4.15 71.2/3.88 73.7/3.32 70.6/3.67 18.1/1.25
3,3 aLRhap 101.8/5.27 79.3/4.05 71.5/3.82 73.5/3.49 70.6/3.69 18.1/1.33
3,2 aDGlcp 98.7/4.92 72.8/3.54 74.1/3.78 70.7/3.52 73.5/3.83 61.9/3.82-3.85
3 aLRhap 99.2/5.05 77.3/3.86 75.8/3.96 73.7/3.71 70.9/4.02 17.6/1.26
2 Ac 23.9/2.08
bDGlcpN 103.6/4.73 57.1/3.84 83.0/3.65 69.7/3.55 77.3/3.46 62.2/3.76-3.91
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2 | aLRhap | 5.14 | 4.15 | 3.88 | 3.32 | 3.67 | 1.25 |
| 3,3 | aLRhap | 5.27 | 4.05 | 3.82 | 3.49 | 3.69 | 1.33 |
| 3,2 | aDGlcp | 4.92 | 3.54 | 3.78 | 3.52 | 3.83 | 3.82
3.85 |
| 3 | aLRhap | 5.05 | 3.86 | 3.96 | 3.71 | 4.02 | 1.26 |
| 2 | Ac |
| 2.08 | |
| | bDGlcpN | 4.73 | 3.84 | 3.65 | 3.55 | 3.46 | 3.76
3.91 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2 | aLRhap | 102.5 | 80.1 | 71.2 | 73.7 | 70.6 | 18.1 |
| 3,3 | aLRhap | 101.8 | 79.3 | 71.5 | 73.5 | 70.6 | 18.1 |
| 3,2 | aDGlcp | 98.7 | 72.8 | 74.1 | 70.7 | 73.5 | 61.9 |
| 3 | aLRhap | 99.2 | 77.3 | 75.8 | 73.7 | 70.9 | 17.6 |
| 2 | Ac | 175.8 | 23.9 | |
| | bDGlcpN | 103.6 | 57.1 | 83.0 | 69.7 | 77.3 | 62.2 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
