Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 23333950Publication DOI: 10.1016/j.carres.2012.11.015Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
The O-polysaccharide (O-antigen) was isolated by mild acid degradation of the lipopolysaccharide (LPS) of Escherichia coli O110. The following structure of the linear tetrasaccharide O-unit of the O-polysaccharide was established by sugar analysis along with 1D and 2D 1H and 13C NMR spectroscopy: →4)[D-aThr-(2→6)]-α-D-GalpA-(1→4)-α-D-Galp-(1--3)-α-D-Galp-(1→3)-β-D-GlcpNAc-(→ where aThr indicates allothreonine. The O-antigen gene cluster of E. coli O110 was sequenced. The gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in full agreement with the O-antigen structure.
O-antigen, Escherichia coli, bacterial polysaccharide structure, O-antigen gene cluster, allothreonine, galacturonamide
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.58
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115013,IEDB_115136,IEDB_130645,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_742246,IEDB_918313,SB_7,SB_87
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, DNA sequencing, sugar analysis, GLC, mild acid hydrolysis, NMR-1D
Biosynthesis and genetic data: genetic data
NCBI Taxonomy refs (TaxIDs): 2491874
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,4,6 xDaThr 174.2 59.7 69.3 19.4
3,3,4 aDGlcpA 101.3 70.0 70.4 78.6 73.0 172.2
3,3 aDGalp 96.8 69.6 69.9 79.0 72.7 61.5
3 aDGalp 100.6 68.4 76.1 66.9 71.9 61.9
2 Ac 175.7 23.8
bDGlcpN 102.9 55.6 81.5 72.9 76.1 63.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,4,6 xDaThr - 4.45 4.15 1.24
3,3,4 aDGlcpA 5.05 3.77 4.05 4.33 4.91 -
3,3 aDGalp 5.17 3.89 4.02 4.14 4.23 3.84-3.84
3 aDGalp 5.41 3.95 3.92 4.21 3.88 3.74-3.74
2 Ac - 2.05
bDGlcpN 4.79 3.75 3.74 3.51 3.35 3.61-3.83
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,4,6 xDaThr 59.7/4.45 69.3/4.15 19.4/1.24
3,3,4 aDGlcpA 101.3/5.05 70.0/3.77 70.4/4.05 78.6/4.33 73.0/4.91
3,3 aDGalp 96.8/5.17 69.6/3.89 69.9/4.02 79.0/4.14 72.7/4.23 61.5/3.84-3.84
3 aDGalp 100.6/5.41 68.4/3.95 76.1/3.92 66.9/4.21 71.9/3.88 61.9/3.74-3.74
2 Ac 23.8/2.05
bDGlcpN 102.9/4.79 55.6/3.75 81.5/3.74 72.9/3.51 76.1/3.35 63.0/3.61-3.83
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,4,6 | xDaThr |
| 4.45 | 4.15 | 1.24 | |
| 3,3,4 | aDGlcpA | 5.05 | 3.77 | 4.05 | 4.33 | 4.91 |
|
| 3,3 | aDGalp | 5.17 | 3.89 | 4.02 | 4.14 | 4.23 | 3.84
3.84 |
| 3 | aDGalp | 5.41 | 3.95 | 3.92 | 4.21 | 3.88 | 3.74
3.74 |
| 2 | Ac |
| 2.05 | |
| | bDGlcpN | 4.79 | 3.75 | 3.74 | 3.51 | 3.35 | 3.61
3.83 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,4,6 | xDaThr | 174.2 | 59.7 | 69.3 | 19.4 | |
| 3,3,4 | aDGlcpA | 101.3 | 70.0 | 70.4 | 78.6 | 73.0 | 172.2 |
| 3,3 | aDGalp | 96.8 | 69.6 | 69.9 | 79.0 | 72.7 | 61.5 |
| 3 | aDGalp | 100.6 | 68.4 | 76.1 | 66.9 | 71.9 | 61.9 |
| 2 | Ac | 175.7 | 23.8 | |
| | bDGlcpN | 102.9 | 55.6 | 81.5 | 72.9 | 76.1 | 63.0 |
|
There is only one chemically distinct structure:
Found 
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