Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: functional gastrointestinal disorders [ICD11:
DD9Y 
];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 24607538Publication DOI: 10.1016/j.carres.2014.02.013Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Perepelov <perepel
ioc.ac.ru>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Institute of Immunology, Federal Medical-Biological Agency, Moscow, Russia
O-Polysaccharide (O-antigen) accompanied by a minor mannan was isolated from the lipopolysaccharide of Escherichia coli O39 and studied by component analyses, methylation, Smith degradation, mass spectrometry, and 1D and 2D NMR spectroscopy. In addition, a new approach, solvolysis with anhydrous trifluoroacetic acid, was applied to cleave selectively the rhamnosidic linkage. The following structure of the O-polysaccharide was established: →3)-β-D-Quip4N(R3Hb)-(1→2)[α-D-Galp(l→3)]-α-D-Manp-(l→4)-α-L-Rhap-(1→3)-α-D-GlcpNAc-(1→ where D-Qui4N(R3Hb) indicates 4,6-dideoxy-4-[(R)-3-hydroxybutanoylamino]-D-glucose. The O-antigen gene cluster of E. coli O39 has been sequenced. The gene functions were tentatively assigned by a comparison with sequences in the available databases and found to be in agreement with the O-polysaccharide structure.
Lipopolysaccharide, O-antigen, Escherichia coli, bacterial polysaccharide structure, O-antigen gene cluster
Structure type: oligomer
Location inside paper: p.32, table 1, p.33, chart 1, OS-2
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144983,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, DNA sequencing, sugar analysis, ESI-MS, mild acid hydrolysis, Smith degradation, NMR-1D, GPC, analysis of gene, solvolysis with trifluoroacetic acid
Biosynthesis and genetic data: genetic data
Comments, role: major product of solvolysis OPS with anhydrous CF3CO2H
Related record ID(s): 30116, 30426, 30427, 30428
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,2,3,2 Ac 175.5 23.5
4,2,3 aDGlcpN 98.5 54.9 72.3 70.7 72.9 61.2
4,2,4 lR3HOBut 175.0 46.2 66.2 23.5
4,2 bDQuip4N 103.7 73.5 78.7 57.4 72.1 18.2
4,3 aDGalp 101.7 70.0 70.7 70.8 72.7 62.7
4 aDManp 100.7 79.7 76.4 67.4 74.3 61.2
bLRhap 94.8 72.8 73.8 82.7 72.1 18.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,2,3,2 Ac - 2.06-2.07
4,2,3 aDGlcpN 5.09 3.88 3.74 3.55 4.15 3.83-3.86
4,2,4 lR3HOBut - 2.36 4.15 1.22
4,2 bDQuip4N 4.44 3.42 3.72 3.82 3.56 1.17
4,3 aDGalp 5.29 3.83 3.89 3.96 4.20 3.71-3.77
4 aDManp 5.07 4.21 4.05 3.96 3.98 3.81-3.85
bLRhap 4.86 3.93 3.72 3.47 3.47 1.30
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,2,3,2 Ac 23.5/2.06-2.07
4,2,3 aDGlcpN 98.5/5.09 54.9/3.88 72.3/3.74 70.7/3.55 72.9/4.15 61.2/3.83-3.86
4,2,4 lR3HOBut 46.2/2.36 66.2/4.15 23.5/1.22
4,2 bDQuip4N 103.7/4.44 73.5/3.42 78.7/3.72 57.4/3.82 72.1/3.56 18.2/1.17
4,3 aDGalp 101.7/5.29 70.0/3.83 70.7/3.89 70.8/3.96 72.7/4.20 62.7/3.71-3.77
4 aDManp 100.7/5.07 79.7/4.21 76.4/4.05 67.4/3.96 74.3/3.98 61.2/3.81-3.85
bLRhap 94.8/4.86 72.8/3.93 73.8/3.72 82.7/3.47 72.1/3.47 18.3/1.30
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,2,3,2 | Ac |
| 2.06
2.07 | |
| 4,2,3 | aDGlcpN | 5.09 | 3.88 | 3.74 | 3.55 | 4.15 | 3.83
3.86 |
| 4,2,4 | lR3HOBut |
| 2.36 | 4.15 | 1.22 | |
| 4,2 | bDQuip4N | 4.44 | 3.42 | 3.72 | 3.82 | 3.56 | 1.17 |
| 4,3 | aDGalp | 5.29 | 3.83 | 3.89 | 3.96 | 4.20 | 3.71
3.77 |
| 4 | aDManp | 5.07 | 4.21 | 4.05 | 3.96 | 3.98 | 3.81
3.85 |
| | bLRhap | 4.86 | 3.93 | 3.72 | 3.47 | 3.47 | 1.30 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,2,3,2 | Ac | 175.5 | 23.5 | |
| 4,2,3 | aDGlcpN | 98.5 | 54.9 | 72.3 | 70.7 | 72.9 | 61.2 |
| 4,2,4 | lR3HOBut | 175.0 | 46.2 | 66.2 | 23.5 | |
| 4,2 | bDQuip4N | 103.7 | 73.5 | 78.7 | 57.4 | 72.1 | 18.2 |
| 4,3 | aDGalp | 101.7 | 70.0 | 70.7 | 70.8 | 72.7 | 62.7 |
| 4 | aDManp | 100.7 | 79.7 | 76.4 | 67.4 | 74.3 | 61.2 |
| | bLRhap | 94.8 | 72.8 | 73.8 | 82.7 | 72.1 | 18.3 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
