Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: enterohemorrhagic disease [ICD11:
1A03.3 
, ICD11:
XN6P4 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 27177202Publication DOI: 10.1016/j.carres.2016.04.025Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: yknirel
gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China
The lipopolysaccharide of Escherichia coli O156 was degraded under mild acidic and alkaline conditions and the resulting polysaccharides were studied by sugar analysis and (1)H and (13)C NMR spectroscopy. The following structure of the pentasaccharide repeating unit of the O-polysaccharide was established: where Rpyr indicates R-configurated pyruvic acid acetal. Minor O-acetyl groups also were present and tentatively localized on the Gal residues. The gene cluster for biosynthesis of the O-antigen of E. coli O156 was analyzed and shown to be consistent with the O-polysaccharide structure.
O-antigen, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, pyruvic acid, O-antigen gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.27, chart 1, LPSOH
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151528,IEDB_151531,IEDB_151770,IEDB_152214,IEDB_174333,IEDB_190606,SB_7,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, mild alkaline degradation, NMR-1D, GPC, mild acid degradation, function analysis of gene clusters
Comments, role: O-deacylated lipopolysaccharide (LPSOH) derived by mild acid degradation of the LPS followed by O-deacylation; minor O-Ac tentatively localized on the Gal residues.
Related record ID(s): 11631
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,6,3,6 xRPyr 175.7 100.9 26.3
3,3,6,3 aDGalp 101.5 69.6 69.1 72.9 63.94 66.3
3,3,6 aLFucp 99.8 69.3 75.4 78.9 68.3 17.1
3,3 aDGalp 101.8 69.9 70.5 70.5 70.7 67.6
3 aLFucp 100.7 68.4 79.7 72.9 68.1 16.6
2 Ac 175.5 23.6
bDGlcpN 102.1 57.1 81.3 70.0 77.5 62.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,6,3,6 xRPyr - - 1.50
3,3,6,3 aDGalp 5.32 3.91 4.02 4.26 3.96 3.90-4.04
3,3,6 aLFucp 4.88 4.02 3.96 4.03 4.06 1.24
3,3 aDGalp 5.19 3.83 3.94 4.05 4.25 3.57-3.85
3 aLFucp 5.02 3.91 3.90 3.95 4.33 1.17
2 Ac - 2.01
bDGlcpN 4.63 3.84 3.69 3.52 3.39 3.67-3.87
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,6,3,6 xRPyr 26.3/1.50
3,3,6,3 aDGalp 101.5/5.32 69.6/3.91 69.1/4.02 72.9/4.26 63.94/3.96 66.3/3.90-4.04
3,3,6 aLFucp 99.8/4.88 69.3/4.02 75.4/3.96 78.9/4.03 68.3/4.06 17.1/1.24
3,3 aDGalp 101.8/5.19 69.9/3.83 70.5/3.94 70.5/4.05 70.7/4.25 67.6/3.57-3.85
3 aLFucp 100.7/5.02 68.4/3.91 79.7/3.90 72.9/3.95 68.1/4.33 16.6/1.17
2 Ac 23.6/2.01
bDGlcpN 102.1/4.63 57.1/3.84 81.3/3.69 70.0/3.52 77.5/3.39 62.3/3.67-3.87
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,6,3,6 | xRPyr |
|
| 1.50 | |
| 3,3,6,3 | aDGalp | 5.32 | 3.91 | 4.02 | 4.26 | 3.96 | 3.90
4.04 |
| 3,3,6 | aLFucp | 4.88 | 4.02 | 3.96 | 4.03 | 4.06 | 1.24 |
| 3,3 | aDGalp | 5.19 | 3.83 | 3.94 | 4.05 | 4.25 | 3.57
3.85 |
| 3 | aLFucp | 5.02 | 3.91 | 3.90 | 3.95 | 4.33 | 1.17 |
| 2 | Ac |
| 2.01 | |
| | bDGlcpN | 4.63 | 3.84 | 3.69 | 3.52 | 3.39 | 3.67
3.87 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,6,3,6 | xRPyr | 175.7 | 100.9 | 26.3 | |
| 3,3,6,3 | aDGalp | 101.5 | 69.6 | 69.1 | 72.9 | 63.94 | 66.3 |
| 3,3,6 | aLFucp | 99.8 | 69.3 | 75.4 | 78.9 | 68.3 | 17.1 |
| 3,3 | aDGalp | 101.8 | 69.9 | 70.5 | 70.5 | 70.7 | 67.6 |
| 3 | aLFucp | 100.7 | 68.4 | 79.7 | 72.9 | 68.1 | 16.6 |
| 2 | Ac | 175.5 | 23.6 | |
| | bDGlcpN | 102.1 | 57.1 | 81.3 | 70.0 | 77.5 | 62.3 |
|
There is only one chemically distinct structure:
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