Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 17182015Publication DOI: 10.1016/j.carres.2006.11.023Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm <gw
organ.su.se>
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Bacteriology, Karolinska University Hospital, Stockholm, Sweden
The O-antigen of the lipopolysaccharide from Escherichia coli O166 has been determined by component analysis together with 1D and 2D NMR spectroscopy techniques. The polysaccharide has pentasaccharide repeating units consisting of d-glucose (1), d-galactose (2) and N-acetyl-d-galactosamine (2) with the following structure: In the (1)H NMR, spectrum resonances of low intensity were observed. Further analysis of these showed that they originate from the terminal part of the polysaccharide, thereby revealing that the repeating unit has a 3-substituted N-acetyl-d-galactosamine residue at its reducing end
Lipopolysaccharide, NMR, Escherichia coli, biological repeating unit
Structure type: suggested polymer biological repeating unit
Location inside paper: p.275, Table 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134624,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_144989,IEDB_146664,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_885822,IEDB_983931,SB_163,SB_192,SB_21,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, NMR-1D, serological methods
Related record ID(s): 25329, 25750, 30394
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G70929JC, GlycomeDB:
34695
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,6 aDGalp 100.7 68.3 79.8 70.3 72.0 62.0
3,4 aDGalp 100.1 69.5 69.9 69.0 69.5 65.1
3,2 Ac 175.4 22.9
3,3 bDGlcp 105.9 73.7 76.1 70.6 76.7 61.5
3 aDGalpN 94.7 49.5 76.9 76.0 72.9 60.5
2 Ac 175.8 23.2
bDGalpN 103.6 51.7 75.6 64.6 75.9 62.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,6 aDGalp 4.93 3.85 4.04 4.19 3.95 3.73
3,4 aDGalp 5.00 3.82 4.03 4.09 4.61 3.73-3.79
3,2 Ac - 2.01
3,3 bDGlcp 4.45 3.39 3.46 3.39 3.39 3.73-3.88
3 aDGalpN 5.08 4.49 3.90 4.29 3.93 3.84
2 Ac - 2.05
bDGalpN 4.68 4.08 3.82 4.10 3.64 3.75-3.81
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,6 aDGalp 100.7/4.93 68.3/3.85 79.8/4.04 70.3/4.19 72.0/3.95 62.0/3.73
3,4 aDGalp 100.1/5.00 69.5/3.82 69.9/4.03 69.0/4.09 69.5/4.61 65.1/3.73-3.79
3,2 Ac 22.9/2.01
3,3 bDGlcp 105.9/4.45 73.7/3.39 76.1/3.46 70.6/3.39 76.7/3.39 61.5/3.73-3.88
3 aDGalpN 94.7/5.08 49.5/4.49 76.9/3.90 76.0/4.29 72.9/3.93 60.5/3.84
2 Ac 23.2/2.05
bDGalpN 103.6/4.68 51.7/4.08 75.6/3.82 64.6/4.10 75.9/3.64 62.2/3.75-3.81
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,6 | aDGalp | 4.93 | 3.85 | 4.04 | 4.19 | 3.95 | 3.73 |
| 3,4 | aDGalp | 5.00 | 3.82 | 4.03 | 4.09 | 4.61 | 3.73
3.79 |
| 3,2 | Ac |
| 2.01 | |
| 3,3 | bDGlcp | 4.45 | 3.39 | 3.46 | 3.39 | 3.39 | 3.73
3.88 |
| 3 | aDGalpN | 5.08 | 4.49 | 3.90 | 4.29 | 3.93 | 3.84 |
| 2 | Ac |
| 2.05 | |
| | bDGalpN | 4.68 | 4.08 | 3.82 | 4.10 | 3.64 | 3.75
3.81 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,6 | aDGalp | 100.7 | 68.3 | 79.8 | 70.3 | 72.0 | 62.0 |
| 3,4 | aDGalp | 100.1 | 69.5 | 69.9 | 69.0 | 69.5 | 65.1 |
| 3,2 | Ac | 175.4 | 22.9 | |
| 3,3 | bDGlcp | 105.9 | 73.7 | 76.1 | 70.6 | 76.7 | 61.5 |
| 3 | aDGalpN | 94.7 | 49.5 | 76.9 | 76.0 | 72.9 | 60.5 |
| 2 | Ac | 175.8 | 23.2 | |
| | bDGalpN | 103.6 | 51.7 | 75.6 | 64.6 | 75.9 | 62.2 |
|
There is only one chemically distinct structure:
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