Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 18237723Publication DOI: 10.1016/j.carres.2008.01.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm <gw
organ.su.se>
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
The structure of the O-antigen polysaccharide (PS) from Escherichia coli O176 has been determined. Component analysis together with (1)H and (13)C NMR spectroscopy was employed to elucidate the structure. Inter-residue correlations were determined by (1)H, (1)H NOESY and (1)H, (13)C heteronuclear multiple-bond correlation experiments. The PS is composed of tetrasaccharide repeating units with the following structure: Cross-peaks of low intensity from α-linked mannopyranosyl residues were present in the (1)H, (1)H TOCSY NMR spectra and further analysis of these showed that they originate from the terminal part of the polysaccharide. Consequently, the biological repeating unit has a 3-substituted N-acetyl-d-galactosamine residue at its reducing end. The repeating unit of the E. coli O176 O-antigen is similar to those from E. coli O17 and O77, thereby explaining the reported cross-reactivities between the strains, and identical to that of Salmonella cerro (O:6, 14, 18)
Lipopolysaccharide, NMR, Escherichia coli, biological repeating unit, Salmonella cerro
Structure type: suggested polymer biological repeating unit
Location inside paper: p.805, abstract, p. 807
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130701,IEDB_136104,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_140116,IEDB_141584,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_885822,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, sugar analysis, GLC, mild acid hydrolysis, NMR-1D
Related record ID(s): 9250, 23197, 23198, 25631, 26211, 108631, 115468
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G82509QD, GlycomeDB:
3519
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,2 aDManp 102.69 71.15 71.96 74.63 72.53 61.05
3,2 aDManp 100.46 78.96 70.98 67.21 73.07 61.88
3 bDManp 102.20 76.73 74.57 67.84 77.69 61.88
2 Ac 174.84 22.90
aDGalpN 99.18 49.97 77.40 69.38 72.45 61.88
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,2 aDManp 5.06 4.01 4.045 3.82 3.80 3.82
3,2 aDManp 5.35 4.12 4.04 3.82 4.05 3.75-3.84
3 bDManp 4.81 4.01 3.75 3.62 3.41 3.4-3.95
2 Ac - 2.06
aDGalpN 5.33 4.31 4.00 4.19 4.03 3.75
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,2 aDManp 102.69/5.06 71.15/4.01 71.96/4.045 74.63/3.82 72.53/3.80 61.05/3.82
3,2 aDManp 100.46/5.35 78.96/4.12 70.98/4.04 67.21/3.82 73.07/4.05 61.88/3.75-3.84
3 bDManp 102.20/4.81 76.73/4.01 74.57/3.75 67.84/3.62 77.69/3.41 61.88/3.4-3.95
2 Ac 22.90/2.06
aDGalpN 99.18/5.33 49.97/4.31 77.40/4.00 69.38/4.19 72.45/4.03 61.88/3.75
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,2 | aDManp | 5.06 | 4.01 | 4.045 | 3.82 | 3.80 | 3.82 |
| 3,2 | aDManp | 5.35 | 4.12 | 4.04 | 3.82 | 4.05 | 3.75
3.84 |
| 3 | bDManp | 4.81 | 4.01 | 3.75 | 3.62 | 3.41 | 3.4
3.95 |
| 2 | Ac |
| 2.06 | |
| | aDGalpN | 5.33 | 4.31 | 4.00 | 4.19 | 4.03 | 3.75 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,2 | aDManp | 102.69 | 71.15 | 71.96 | 74.63 | 72.53 | 61.05 |
| 3,2 | aDManp | 100.46 | 78.96 | 70.98 | 67.21 | 73.07 | 61.88 |
| 3 | bDManp | 102.20 | 76.73 | 74.57 | 67.84 | 77.69 | 61.88 |
| 2 | Ac | 174.84 | 22.90 | |
| | aDGalpN | 99.18 | 49.97 | 77.40 | 69.38 | 72.45 | 61.88 |
|
There is only one chemically distinct structure:
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Displayed record 1
