Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 22015401Publication DOI: 10.1016/j.carres.2011.09.013Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
The O-polysaccharide (O-antigen) of Escherichia coli O19ab was studied by sugar analysis along with 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure of the linear pentasaccharide repeating unit was established: [See formula in text] where the degree of O-acetylation of GlcNAc is ?33%. The O-antigen gene cluster of E. coli O19ab was sequenced. The gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in full agreement with the E. coli O19ab-antigen structure.
Lipopolysaccharide, O-antigen, Escherichia coli, bacterial polysaccharide structure, O-antigen gene cluster
Structure type: suggested polymer biological repeating unit
Location inside paper: table 1, p.2813, DPS
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144825,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, acid hydrolysis, GLC, de-O-acetylation, NMR-1D, delipidation, function analysis of gene clusters
Biosynthesis and genetic data: genetic data
Comments, role: the O-deacetylated OPS
Related record ID(s): 26310, 27161, 30310
NCBI Taxonomy refs (TaxIDs): 1095707Reference(s) to other database(s): GTC:G27270SE
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,2,2 aLRhap 100.7 77.5 70.5 73.2 70.7 18.0
3,2,2 aLRhap 102.0 79.6 71.0 73.4 70.5 17.8
3,2 aLRhap 101.3 79.0 71.1 73.2 70.5 17.9
3 aDGlcp 99.1 77.4 73.9 70.7 73.5 61.7
2 Ac 175.3 23.4
aDGlcpN 97.5 53.2 76.7 72.1 73.2 61.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,2,2 aLRhap 5.01 4.08 3.91 3.51 3.77 1.30
3,2,2 aLRhap 5.13 4.09 3.87 3.45 3.68 1.27
3,2 aLRhap 5.23 4.06 3.87 3.51 3.85 1.29
3 aDGlcp 5.49 3.66 3.74 3.43 3.68 3.74-3.86
2 Ac - 2.06
aDGlcpN 4.98 4.10 3.99 3.75 4.06 3.81-3.81
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,2,2 aLRhap 100.7/5.01 77.5/4.08 70.5/3.91 73.2/3.51 70.7/3.77 18.0/1.30
3,2,2 aLRhap 102.0/5.13 79.6/4.09 71.0/3.87 73.4/3.45 70.5/3.68 17.8/1.27
3,2 aLRhap 101.3/5.23 79.0/4.06 71.1/3.87 73.2/3.51 70.5/3.85 17.9/1.29
3 aDGlcp 99.1/5.49 77.4/3.66 73.9/3.74 70.7/3.43 73.5/3.68 61.7/3.74-3.86
2 Ac 23.4/2.06
aDGlcpN 97.5/4.98 53.2/4.10 76.7/3.99 72.1/3.75 73.2/4.06 61.2/3.81-3.81
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,2,2 | aLRhap | 5.01 | 4.08 | 3.91 | 3.51 | 3.77 | 1.30 |
| 3,2,2 | aLRhap | 5.13 | 4.09 | 3.87 | 3.45 | 3.68 | 1.27 |
| 3,2 | aLRhap | 5.23 | 4.06 | 3.87 | 3.51 | 3.85 | 1.29 |
| 3 | aDGlcp | 5.49 | 3.66 | 3.74 | 3.43 | 3.68 | 3.74
3.86 |
| 2 | Ac |
| 2.06 | |
| | aDGlcpN | 4.98 | 4.10 | 3.99 | 3.75 | 4.06 | 3.81
3.81 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,2,2 | aLRhap | 100.7 | 77.5 | 70.5 | 73.2 | 70.7 | 18.0 |
| 3,2,2 | aLRhap | 102.0 | 79.6 | 71.0 | 73.4 | 70.5 | 17.8 |
| 3,2 | aLRhap | 101.3 | 79.0 | 71.1 | 73.2 | 70.5 | 17.9 |
| 3 | aDGlcp | 99.1 | 77.4 | 73.9 | 70.7 | 73.5 | 61.7 |
| 2 | Ac | 175.3 | 23.4 | |
| | aDGlcpN | 97.5 | 53.2 | 76.7 | 72.1 | 73.2 | 61.2 |
|
There is only one chemically distinct structure:
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