Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 29220644Publication DOI: 10.1016/j.carres.2017.11.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Perepelov <andreivperepelov
gmail.com>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin, 300457, China
The O-specific polysaccharide (O-antigen) is a part of the lipopolysaccharide on the cell surface of Gram-negative bacteria. The O-polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O27 and studied by sugar analysis and Smith degradation along with 1H and 13C NMR spectroscopy. The following structure of the branched hexasaccharide repeating unit was established, which is unique among known structures of bacterial polysaccharides:where GlcA is non-stoichiometrically O-acetylated at position 3 (∼22%) or 4 (∼37%). Functions of genes in the O-antigen gene cluster of E. coli O27 were tentatively assigned by comparison with sequences in the available databases and found to be consistent with the O-polysaccharide structure.
Lipopolysaccharide, O-antigen, Escherichia coli, O-specific polysaccharide, O-antigen gene cluster, O-Polysaccharide structure
Structure type: polymer chemical repeating unit
Location inside paper: p.3, table 1, O-deacetylated OPS
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_423153,IEDB_983931,SB_192,SB_25,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, Smith degradation, de-O-acetylation, GPC, delipidation, function analysis of gene clusters
Comments, role: O-deacetylated polysaccharide from E. coli O27 type strain E1020-72 (laboratory stock number G1285).
Related record ID(s): 12460
NCBI Taxonomy refs (TaxIDs): 1095710Reference(s) to other database(s): GTC:G88466PI
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,6,2 bDGlcp 105.3 74.6 76.9 70.9 77.1 62.2
3,6,3 bDGlcpA 104.8 74.7 76.8 73.1 77.6 175.2
3,6 aDGalp 99.4 77.4 80.1 78.9 70.6 62.4
3 bDGlcp 105.6 74.3 76.9 70.7 75.4 67.
2 Ac 176.6 24.3
6 bDGlcp 103.9 74.3 76.8 71.9 77.2 62.2
bDGalpN 103.4 52.6 82.0 69.0 75.3 70.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,6,2 bDGlcp 4.52 3.34 3.47 3.43 3.44 3.76-3.91
3,6,3 bDGlcpA 4.61 3.42 3.54 3.57 3.73 -
3,6 aDGalp 5.14 3.95 4.08 4.34 4.10 3.78-3.78
3 bDGlcp 4.59 3.31 3.48 3.57 3.62 3.78-4.00
2 Ac - 2.02
6 bDGlcp 4.47 3.27 3.48 3.39 3.45 3.74-3.90
bDGalpN 4.75 3.97 3.89 4.12 3.60 3.89-3.89
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,6,2 bDGlcp 105.3/4.52 74.6/3.34 76.9/3.47 70.9/3.43 77.1/3.44 62.2/3.76-3.91
3,6,3 bDGlcpA 104.8/4.61 74.7/3.42 76.8/3.54 73.1/3.57 77.6/3.73
3,6 aDGalp 99.4/5.14 77.4/3.95 80.1/4.08 78.9/4.34 70.6/4.10 62.4/3.78-3.78
3 bDGlcp 105.6/4.59 74.3/3.31 76.9/3.48 70.7/3.57 75.4/3.62 67./3.78-4.00
2 Ac 24.3/2.02
6 bDGlcp 103.9/4.47 74.3/3.27 76.8/3.48 71.9/3.39 77.2/3.45 62.2/3.74-3.90
bDGalpN 103.4/4.75 52.6/3.97 82.0/3.89 69.0/4.12 75.3/3.60 70.9/3.89-3.89
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,6,2 | bDGlcp | 4.52 | 3.34 | 3.47 | 3.43 | 3.44 | 3.76
3.91 |
| 3,6,3 | bDGlcpA | 4.61 | 3.42 | 3.54 | 3.57 | 3.73 |
|
| 3,6 | aDGalp | 5.14 | 3.95 | 4.08 | 4.34 | 4.10 | 3.78
3.78 |
| 3 | bDGlcp | 4.59 | 3.31 | 3.48 | 3.57 | 3.62 | 3.78
4.00 |
| 2 | Ac |
| 2.02 | |
| 6 | bDGlcp | 4.47 | 3.27 | 3.48 | 3.39 | 3.45 | 3.74
3.90 |
| | bDGalpN | 4.75 | 3.97 | 3.89 | 4.12 | 3.60 | 3.89
3.89 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,6,2 | bDGlcp | 105.3 | 74.6 | 76.9 | 70.9 | 77.1 | 62.2 |
| 3,6,3 | bDGlcpA | 104.8 | 74.7 | 76.8 | 73.1 | 77.6 | 175.2 |
| 3,6 | aDGalp | 99.4 | 77.4 | 80.1 | 78.9 | 70.6 | 62.4 |
| 3 | bDGlcp | 105.6 | 74.3 | 76.9 | 70.7 | 75.4 | 67. |
| 2 | Ac | 176.6 | 24.3 | |
| 6 | bDGlcp | 103.9 | 74.3 | 76.8 | 71.9 | 77.2 | 62.2 |
| | bDGalpN | 103.4 | 52.6 | 82.0 | 69.0 | 75.3 | 70.9 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
