Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
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: abstract, p.1597, chart 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_130671,IEDB_130692,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_158539,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: Escherichia coli O129 strain G1096; NMR for -2)aLRhap4Ac(1- 1H: 5.13 4.25 4.11 4.78 3.84 1.13; 13C: 102.3 78.6 69.8 75.5 68.3 17.8
Related record ID(s): 329, 25391, 25805
NCBI Taxonomy refs (TaxIDs): 562,
424718Reference(s) to other database(s): GTC:G93405KK
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2,3 35%Ac 175.0 21.9
3,3,2,4 25%Ac 175.2 21.7
3,3,2 aLRhap 102.2 77.9 74.0 71.5 71.5 17.9
3,3,3 aDGlcp 95.7 72.4 74.2 70.8 72.9 61.8
3,3 aLRhap 101.7 76.0 74.7 71.7 70.3 18.0
3 aLRhap 102.3 71.8 78.4 73.0 70.2 17.6
2 Ac 175.7 23.5
bDGlcpN 103.1 56.9 82.4 69.7 77.0 62.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2,3 35%Ac - 2.20
3,3,2,4 25%Ac - 2.15
3,3,2 aLRhap 5.15 4.24 5.09 3.50 3.78 1.27
3,3,3 aDGlcp 5.08 3.58 3.78 3.44 3.92 3.76-3.84
3,3 aLRhap 5.27 4.29 3.99 3.65 3.78 1.34
3 aLRhap 4.89 3.85 3.78 3.55 4.00 1.23
2 Ac - 2.06
bDGlcpN 4.57 3.83 3.66 3.51 3.43 3.73-3.93
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2,3 35%Ac 21.9/2.20
3,3,2,4 25%Ac 21.7/2.15
3,3,2 aLRhap 102.2/5.15 77.9/4.24 74.0/5.09 71.5/3.50 71.5/3.78 17.9/1.27
3,3,3 aDGlcp 95.7/5.08 72.4/3.58 74.2/3.78 70.8/3.44 72.9/3.92 61.8/3.76-3.84
3,3 aLRhap 101.7/5.27 76.0/4.29 74.7/3.99 71.7/3.65 70.3/3.78 18.0/1.34
3 aLRhap 102.3/4.89 71.8/3.85 78.4/3.78 73.0/3.55 70.2/4.00 17.6/1.23
2 Ac 23.5/2.06
bDGlcpN 103.1/4.57 56.9/3.83 82.4/3.66 69.7/3.51 77.0/3.43 62.2/3.73-3.93
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2,3 | 35%Ac |
| 2.20 | |
| 3,3,2,4 | 25%Ac |
| 2.15 | |
| 3,3,2 | aLRhap | 5.15 | 4.24 | 5.09 | 3.50 | 3.78 | 1.27 |
| 3,3,3 | aDGlcp | 5.08 | 3.58 | 3.78 | 3.44 | 3.92 | 3.76
3.84 |
| 3,3 | aLRhap | 5.27 | 4.29 | 3.99 | 3.65 | 3.78 | 1.34 |
| 3 | aLRhap | 4.89 | 3.85 | 3.78 | 3.55 | 4.00 | 1.23 |
| 2 | Ac |
| 2.06 | |
| | bDGlcpN | 4.57 | 3.83 | 3.66 | 3.51 | 3.43 | 3.73
3.93 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2,3 | 35%Ac | 175.0 | 21.9 | |
| 3,3,2,4 | 25%Ac | 175.2 | 21.7 | |
| 3,3,2 | aLRhap | 102.2 | 77.9 | 74.0 | 71.5 | 71.5 | 17.9 |
| 3,3,3 | aDGlcp | 95.7 | 72.4 | 74.2 | 70.8 | 72.9 | 61.8 |
| 3,3 | aLRhap | 101.7 | 76.0 | 74.7 | 71.7 | 70.3 | 18.0 |
| 3 | aLRhap | 102.3 | 71.8 | 78.4 | 73.0 | 70.2 | 17.6 |
| 2 | Ac | 175.7 | 23.5 | |
| | bDGlcpN | 103.1 | 56.9 | 82.4 | 69.7 | 77.0 | 62.2 |
|
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
