Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 27454490Publication DOI: 10.1016/j.carres.2016.07.011Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: yknirel
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, TEDA, Tianjin, China
Mild alkaline degradation of the lipopolysaccharide of Escherichia coli O80 afforded a polysaccharide, which was studied by sugar analysis, selective cleavage of glycosidic linkages, and (1)H and (13)C NMR spectroscopy. Solvolysis of the polysaccharide with CF3CO2H cleaved the linkages of α-Fuc and β-linked GlcNAc and GalNAc residues to give two disaccharides. The following structure of the hexasaccharide repeating unit of the O-polysaccharide was established: The polysaccharide repeat also contains a minor O-acetyl group but its position was not determined. The O-antigen gene cluster of E. coli O80 between the conserved galF and gnd genes was analyzed and found to be consistent with the O-polysaccharide structure established.
O-antigen, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, O-antigen gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.86, chart 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_135813,IEDB_136045,IEDB_137340,IEDB_137473,IEDB_140630,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_151527,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_423096,IEDB_423153,IEDB_983931,SB_192,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, Smith degradation, NMR-1D, GPC, mild acid degradation, function analysis of gene clusters, solvolysis with trifluoroacetic acid
Comments, role: E. coli O80 (laboratory stock number G1076); the OPS units contains a minor OAc but its position was not determined.
Related record ID(s): 11656, 11657, 11658, 11659, 11660
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G23440UK
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,3,2 aLFucp 100.2 69.3 70.7 72.9-73.1 67.8 16.3
3,4,3 bDGlcp 102.8 79.0 77.9 70.7 75.5 69.3
3,4,2 Ac 174.8-175.3 23.5-23.6
3,4 bDGalpN 103.2 52.4 77.9 69.1 76.1 62.0
3 bDGlcpA 103.9 73.6 74.8 81.4 76.4 172.9
2 Ac 174.8-175.3 23.5-23.6
4 aLFucp 99.4 69.3 70.3 72.9-73.1 67.5 16.5
bDGlcpN 102.3 56.6 78.4 74.2 76.7 61.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,3,2 aLFucp 5.25 3.78 3.67 3.74 4.20 1.20
3,4,3 bDGlcp 4.62 3.43 3.67 3.45 3.50 3.84-4.04
3,4,2 Ac - 2.02-2.08
3,4 bDGalpN 4.48 3.91 3.89 4.08 3.74 3.80
3 bDGlcpA 4.59 3.26 3.63 3.72 3.73 -
2 Ac - 2.02-2.08
4 aLFucp 4.98 3.77 3.75 3.74 4.71 1.17
bDGlcpN 4.57 3.97 4.03 3.71 3.56 3.87-3.99
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,3,2 aLFucp 100.2/5.25 69.3/3.78 70.7/3.67 72.9-73.1/3.74 67.8/4.20 16.3/1.20
3,4,3 bDGlcp 102.8/4.62 79.0/3.43 77.9/3.67 70.7/3.45 75.5/3.50 69.3/3.84-4.04
3,4,2 Ac 23.5-23.6/2.02-2.08
3,4 bDGalpN 103.2/4.48 52.4/3.91 77.9/3.89 69.1/4.08 76.1/3.74 62.0/3.80
3 bDGlcpA 103.9/4.59 73.6/3.26 74.8/3.63 81.4/3.72 76.4/3.73
2 Ac 23.5-23.6/2.02-2.08
4 aLFucp 99.4/4.98 69.3/3.77 70.3/3.75 72.9-73.1/3.74 67.5/4.71 16.5/1.17
bDGlcpN 102.3/4.57 56.6/3.97 78.4/4.03 74.2/3.71 76.7/3.56 61.1/3.87-3.99
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,3,2 | aLFucp | 5.25 | 3.78 | 3.67 | 3.74 | 4.20 | 1.20 |
| 3,4,3 | bDGlcp | 4.62 | 3.43 | 3.67 | 3.45 | 3.50 | 3.84
4.04 |
| 3,4,2 | Ac |
| 2.02
2.08 | |
| 3,4 | bDGalpN | 4.48 | 3.91 | 3.89 | 4.08 | 3.74 | 3.80 |
| 3 | bDGlcpA | 4.59 | 3.26 | 3.63 | 3.72 | 3.73 |
|
| 2 | Ac |
| 2.02
2.08 | |
| 4 | aLFucp | 4.98 | 3.77 | 3.75 | 3.74 | 4.71 | 1.17 |
| | bDGlcpN | 4.57 | 3.97 | 4.03 | 3.71 | 3.56 | 3.87
3.99 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,3,2 | aLFucp | 100.2 | 69.3 | 70.7 | 72.9
73.1 | 67.8 | 16.3 |
| 3,4,3 | bDGlcp | 102.8 | 79.0 | 77.9 | 70.7 | 75.5 | 69.3 |
| 3,4,2 | Ac | 174.8
175.3 | 23.5
23.6 | |
| 3,4 | bDGalpN | 103.2 | 52.4 | 77.9 | 69.1 | 76.1 | 62.0 |
| 3 | bDGlcpA | 103.9 | 73.6 | 74.8 | 81.4 | 76.4 | 172.9 |
| 2 | Ac | 174.8
175.3 | 23.5
23.6 | |
| 4 | aLFucp | 99.4 | 69.3 | 70.3 | 72.9
73.1 | 67.5 | 16.5 |
| | bDGlcpN | 102.3 | 56.6 | 78.4 | 74.2 | 76.7 | 61.1 |
|
There is only one chemically distinct structure:
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Displayed record 1
