Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 20331420Publication DOI: 10.1134/S0006297910010037Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: A.V. Perepelov <perepel
ioc.ac.ru>
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
On mild acid degradation of the lipopolysaccharide of Escherichia coli O108, the O-polysaccharide was isolated and studied by sugar analysis and one- and two-dimensional 1H- and 13C-NMR spectroscopy. The polysaccharide was found to contain an unusual higher sugar, 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-d-galacto-non-2-ulosonic acid (di-N-acetyl-8-epilegionaminic acid, 8eLeg5Ac7Ac). The following structure of the tetrasaccharide repeating unit of the polysaccharide was established: →4)-α-8eLegp5Ac7Ac-(2→6)-α-D-Galp-(1→3)-α-L-FucpNAc-(1→3)-α-D-GlcpNAc-(1→. Functions of the E. coli O108 antigen biosynthetic genes, including seven putative genes for synthesis of 8eLeg5Ac7Ac, were assigned by sequencing the O-antigen gene cluster along with comparison with gene databases and known biosynthetic pathways for related nonulosonic acids.
Lipopolysaccharide, biosynthesis, O-antigen, Escherichia coli, nonulosonic acid, O-antigen gene cluster, O-Polysaccharide structure
Structure type: suggested polymer biological repeating unit
Location inside paper: abstract, p.21
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis
Biosynthesis and genetic data: characterization of the O-antigen gene cluster
Related record ID(s): 26823
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G69233GH, GlycomeDB:
37822
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
3,3,6,5 Ac 175.1-176.0 23.1-23.7
3,3,6,7 Ac 175.1-176.0 23.1-23.7
3,3,6 aX8eLegp 174.2 101.0 37.7 72.4 51.6 74.2 53.9 69.4 20.7
3,3 aDGalp 102.5 69.8 70.6 70.3 70.2 63.0
3,2 Ac 175.1-176.0 23.1-23.7
3 aLFucpN 98.9 49.6 77.9 72.5 68.1 17.0
2 Ac 175.1-176.0 23.1-23.7
aDGlcpN 94.7 54.6 77.1 69.4 74.0 62.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
3,3,6,5 Ac - 1.93-2.04
3,3,6,7 Ac - 1.93-2.04
3,3,6 aX8eLegp - - 1.55-2.44 3.95 3.79 4.06 4.00 4.11 1.19
3,3 aDGalp 5.02 3.73 3.84 4.05 4.14 3.38-3.64
3,2 Ac - 1.93-2.04
3 aLFucpN 4.94 4.26 3.88 3.85 4.39 1.20
2 Ac - 1.93-2.04
aDGlcpN 4.86 4.05 3.64 3.54 3.54 3.79-3.82
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
3,3,6,5 Ac 23.1-23.7/1.93-2.04
3,3,6,7 Ac 23.1-23.7/1.93-2.04
3,3,6 aX8eLegp 37.7/1.55-2.44 72.4/3.95 51.6/3.79 74.2/4.06 53.9/4.00 69.4/4.11 20.7/1.19
3,3 aDGalp 102.5/5.02 69.8/3.73 70.6/3.84 70.3/4.05 70.2/4.14 63.0/3.38-3.64
3,2 Ac 23.1-23.7/1.93-2.04
3 aLFucpN 98.9/4.94 49.6/4.26 77.9/3.88 72.5/3.85 68.1/4.39 17.0/1.20
2 Ac 23.1-23.7/1.93-2.04
aDGlcpN 94.7/4.86 54.6/4.05 77.1/3.64 69.4/3.54 74.0/3.54 62.0/3.79-3.82
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 3,3,6,5 | Ac |
| 1.93
2.04 | |
| 3,3,6,7 | Ac |
| 1.93
2.04 | |
| 3,3,6 | aX8eLegp |
|
| 1.55
2.44 | 3.95 | 3.79 | 4.06 | 4.00 | 4.11 | 1.19 |
| 3,3 | aDGalp | 5.02 | 3.73 | 3.84 | 4.05 | 4.14 | 3.38
3.64 | |
| 3,2 | Ac |
| 1.93
2.04 | |
| 3 | aLFucpN | 4.94 | 4.26 | 3.88 | 3.85 | 4.39 | 1.20 | |
| 2 | Ac |
| 1.93
2.04 | |
| | aDGlcpN | 4.86 | 4.05 | 3.64 | 3.54 | 3.54 | 3.79
3.82 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 3,3,6,5 | Ac | 175.1
176.0 | 23.1
23.7 | |
| 3,3,6,7 | Ac | 175.1
176.0 | 23.1
23.7 | |
| 3,3,6 | aX8eLegp | 174.2 | 101.0 | 37.7 | 72.4 | 51.6 | 74.2 | 53.9 | 69.4 | 20.7 |
| 3,3 | aDGalp | 102.5 | 69.8 | 70.6 | 70.3 | 70.2 | 63.0 | |
| 3,2 | Ac | 175.1
176.0 | 23.1
23.7 | |
| 3 | aLFucpN | 98.9 | 49.6 | 77.9 | 72.5 | 68.1 | 17.0 | |
| 2 | Ac | 175.1
176.0 | 23.1
23.7 | |
| | aDGlcpN | 94.7 | 54.6 | 77.1 | 69.4 | 74.0 | 62.0 | |
|
There is only one chemically distinct structure:
Found 
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