Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 9208951Publication DOI: 10.1111/j.1432-1033.1997.00565.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Swedish Insitute of Infectious Disease Control (SMI), Stockholm, Sweden
The structure of the O-antigenic polysaccharide from Escherichia coli O167:H5 has been investigated. Sugar and methylation analyses, fast-atom-bombardment mass spectrometry and 1H- and 13C NMR spectroscopy were the main methods used. The structure of the repeating unit of the polysaccharide was found to be: [formula in text]. Oligosaccharide derivatives of the polysaccharide were obtained by HF solvolysis and by a Smith degradation. Furthermore, base treatment of the polysaccharide led to a degraded polymeric material. For the methylated polysaccharide the amide linkage between alanine and the galacturonic acid residue was reductively cleaved with LiBD4 in ethanol, to give, among other things, a 3-O-methyl galactose derivative.
Lipopolysaccharide, NMR, LPS, structure, structural, polysaccharide, O-antigen, O antigen, Escherichia, Escherichia coli, polysaccharides, structural studies, galactofuranose, galacturonic acid, amide, L-alanine
Structure type: suggested polymer biological repeating unit
Location inside paper: abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_151531,IEDB_190606,IEDB_885812
Methods: methylation, NMR-2D, FAB-MS, partial acid hydrolysis, NMR, sugar analysis, Smith degradation
Related record ID(s): 3229, 3230, 3231, 20707, 23044
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GlycomeDB:
33711
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,5,2,3,4 aDGalf 103.7 76.6 73.5 81.2 70.2 63.8
3,5,2,3,6 xLAla? 180.0 51.3 18.0
3,5,2,3 bDGalpA 101.7 79.5 73.3 79.4 74.2 169.1
3,5,2,2 Ac 174.4 23.1
3,5,2 aDGlcpN 97.6 53.3 79.7 69.5 73.2 61.5
3,5 bDGalf 106.7 87.6 75.8 82.8 70.9 63.7
3 bDGalf 109.0 82.0 77.3 82.5 76.8 62.3
2 Ac 175.0 23.1
bDGlcpN 102.5 55.8 81.7 69.2 76.0 61.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,5,2,3,4 aDGalf 4.90 4.02 4.23 3.83 3.80 3.66-3.7
3,5,2,3,6 xLAla? - 4.16 1.35
3,5,2,3 bDGalpA 4.65 3.59 3.75 4.25 4.21 -
3,5,2,2 Ac - 2.08
3,5,2 aDGlcpN 5.01 4.09 4.00 3.62 3.88 3.85-3.92
3,5 bDGalf 5.23 4.16 4.23 4.06 3.86 3.70-3.70
3 bDGalf 5.03 4.03 4.07 4.15 3.94 3.13-3.73
2 Ac - 2.05
bDGlcpN 4.68 3.82 3.66 3.48 3.44 3.76-3.91
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,5,2,3,4 aDGalf 103.7/4.90 76.6/4.02 73.5/4.23 81.2/3.83 70.2/3.80 63.8/3.66-3.7
3,5,2,3,6 xLAla? 51.3/4.16 18.0/1.35
3,5,2,3 bDGalpA 101.7/4.65 79.5/3.59 73.3/3.75 79.4/4.25 74.2/4.21
3,5,2,2 Ac 23.1/2.08
3,5,2 aDGlcpN 97.6/5.01 53.3/4.09 79.7/4.00 69.5/3.62 73.2/3.88 61.5/3.85-3.92
3,5 bDGalf 106.7/5.23 87.6/4.16 75.8/4.23 82.8/4.06 70.9/3.86 63.7/3.70-3.70
3 bDGalf 109.0/5.03 82.0/4.03 77.3/4.07 82.5/4.15 76.8/3.94 62.3/3.13-3.73
2 Ac 23.1/2.05
bDGlcpN 102.5/4.68 55.8/3.82 81.7/3.66 69.2/3.48 76.0/3.44 61.9/3.76-3.91
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,5,2,3,4 | aDGalf | 4.90 | 4.02 | 4.23 | 3.83 | 3.80 | 3.66
3.7 |
| 3,5,2,3,6 | xLAla? |
| 4.16 | 1.35 | |
| 3,5,2,3 | bDGalpA | 4.65 | 3.59 | 3.75 | 4.25 | 4.21 |
|
| 3,5,2,2 | Ac |
| 2.08 | |
| 3,5,2 | aDGlcpN | 5.01 | 4.09 | 4.00 | 3.62 | 3.88 | 3.85
3.92 |
| 3,5 | bDGalf | 5.23 | 4.16 | 4.23 | 4.06 | 3.86 | 3.70
3.70 |
| 3 | bDGalf | 5.03 | 4.03 | 4.07 | 4.15 | 3.94 | 3.13
3.73 |
| 2 | Ac |
| 2.05 | |
| | bDGlcpN | 4.68 | 3.82 | 3.66 | 3.48 | 3.44 | 3.76
3.91 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,5,2,3,4 | aDGalf | 103.7 | 76.6 | 73.5 | 81.2 | 70.2 | 63.8 |
| 3,5,2,3,6 | xLAla? | 180.0 | 51.3 | 18.0 | |
| 3,5,2,3 | bDGalpA | 101.7 | 79.5 | 73.3 | 79.4 | 74.2 | 169.1 |
| 3,5,2,2 | Ac | 174.4 | 23.1 | |
| 3,5,2 | aDGlcpN | 97.6 | 53.3 | 79.7 | 69.5 | 73.2 | 61.5 |
| 3,5 | bDGalf | 106.7 | 87.6 | 75.8 | 82.8 | 70.9 | 63.7 |
| 3 | bDGalf | 109.0 | 82.0 | 77.3 | 82.5 | 76.8 | 62.3 |
| 2 | Ac | 175.0 | 23.1 | |
| | bDGlcpN | 102.5 | 55.8 | 81.7 | 69.2 | 76.0 | 61.9 |
|
There is only one chemically distinct structure:
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