Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
];
infection due to Shigella boydii [ICD11:
XN8RN ]
The structure was elucidated in this paperNCBI PubMed ID: 27301288Publication DOI: 10.1134/S0006297916060067Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: yknirel
gmail.com
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Nankai University, TEDA Institute of Biological Sciences and Biotechnology, Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, 300457 Tianjin, China
Gene clusters for biosynthesis of 24 of 34 basic O-antigen forms of Shigella spp. are identical or similar to those of the genetically closely related bacterium Escherichia coli. For 18 of these relatedness was confirmed chemically by elucidation of the O-antigen (O-polysaccharide) structures. In this work, structures of the six remaining O-antigens of E. coli O32, O53, O79, O105, O183 (all related to S. boydii serotypes), and O38 (related to S. dysenteriae type 8) were established using (1)H and (13)C NMR spectroscopy. They were found to be identical to the Shigella counterparts, except for the O32- and O38-polysaccharides, which differ in the presence of O-acetyl groups. The structure of the E. coli O105-related O-polysaccharide of S. boydii type 11 proposed earlier is revised. The contents of the O-antigen gene clusters of the related strains of E. coli and Shigella spp. and different mechanisms of O-antigen diversification in these bacteria are discussed in view of the O-polysaccharide structures established. These data illustrate the value of the O-antigen chemistry and genetics for elucidation of evolutionary relationships of bacteria.
Escherichia coli, Shigella dysenteriae, Shigella boydii, O-antigen gene cluster, O-Polysaccharide structure
Structure type: polymer chemical repeating unit
Location inside paper: p.603, fig.4
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_149136,IEDB_151531,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, de-O-acetylation, GPC, mild acid degradation, function analysis of gene clusters
Comments, role: O-Deacetylated OPS of E. coli O105 and S. boydii type 11 (revised structure).
Related record ID(s): 11555, 11556, 11557, 11558, 11559, 11560, 11561, 11562, 11563, 11564, 11565, 11566, 11567, 11568, 11569, 11570, 11571, 11572, 11573
NCBI Taxonomy refs (TaxIDs): 2079153,
621Reference(s) to other database(s): GTC:G69292MA, GlycomeDB:
25719
Show glycosyltransferases
NMR conditions: in D2O at 323 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,3,2,4 bDRibf 109.1 75.7 70.4 83.4 61.7
3,4,3,2 aDGlcpA 98.9 57.0-77.7 72.6 81.6 73.2 ?
3,4,3 aLRhap 101.2 77.7 80.0 70.0-83.8 71.0 17.9
3,4 bLRhap 101.5 71.8 81.9 72.1 73.2 18.0
3 aLRhap 102.2 71.3 70.3 83.8 68.6 17.7
2 Ac 175.5 23.6
bDGlcpN 103.1 57.0 82.4 70.0 76.9 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,3,2,4 bDRibf 4.97 4.14 4.35 4.02 3.73-3.86
3,4,3,2 aDGlcpA 4.99 3.59 3.77 3.50 4.28 -
3,4,3 aLRhap 5.10 4.21 4.03 3.59 3.88 1.30
3,4 bLRhap 4.73 4.12 3.66 3.49 3.48 1.34
3 aLRhap 4.87 3.93 3.86 3.57 4.07 1.26
2 Ac - 2.04
bDGlcpN 4.88 3.74 3.79 3.50 3.45 3.73-3.89
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,3,2,4 bDRibf 109.1/4.97 75.7/4.14 70.4/4.35 83.4/4.02 61.7/3.73-3.86
3,4,3,2 aDGlcpA 98.9/4.99 57.0-77.7/3.59 72.6/3.77 81.6/3.50 73.2/4.28
3,4,3 aLRhap 101.2/5.10 77.7/4.21 80.0/4.03 70.0-83.8/3.59 71.0/3.88 17.9/1.30
3,4 bLRhap 101.5/4.73 71.8/4.12 81.9/3.66 72.1/3.49 73.2/3.48 18.0/1.34
3 aLRhap 102.2/4.87 71.3/3.93 70.3/3.86 83.8/3.57 68.6/4.07 17.7/1.26
2 Ac 23.6/2.04
bDGlcpN 103.1/4.88 57.0/3.74 82.4/3.79 70.0/3.50 76.9/3.45 62.4/3.73-3.89
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,3,2,4 | bDRibf | 4.97 | 4.14 | 4.35 | 4.02 | 3.73
3.86 | |
| 3,4,3,2 | aDGlcpA | 4.99 | 3.59 | 3.77 | 3.50 | 4.28 |
|
| 3,4,3 | aLRhap | 5.10 | 4.21 | 4.03 | 3.59 | 3.88 | 1.30 |
| 3,4 | bLRhap | 4.73 | 4.12 | 3.66 | 3.49 | 3.48 | 1.34 |
| 3 | aLRhap | 4.87 | 3.93 | 3.86 | 3.57 | 4.07 | 1.26 |
| 2 | Ac |
| 2.04 | |
| | bDGlcpN | 4.88 | 3.74 | 3.79 | 3.50 | 3.45 | 3.73
3.89 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,3,2,4 | bDRibf | 109.1 | 75.7 | 70.4 | 83.4 | 61.7 | |
| 3,4,3,2 | aDGlcpA | 98.9 | 57.0
77.7 | 72.6 | 81.6 | 73.2 | ? |
| 3,4,3 | aLRhap | 101.2 | 77.7 | 80.0 | 70.0
83.8 | 71.0 | 17.9 |
| 3,4 | bLRhap | 101.5 | 71.8 | 81.9 | 72.1 | 73.2 | 18.0 |
| 3 | aLRhap | 102.2 | 71.3 | 70.3 | 83.8 | 68.6 | 17.7 |
| 2 | Ac | 175.5 | 23.6 | |
| | bDGlcpN | 103.1 | 57.0 | 82.4 | 70.0 | 76.9 | 62.4 |
|
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The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
