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: polymer chemical repeating unit
Location inside paper: p. 570
Compound class: O-polysaccharide
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
Comments, role: beta-elimenation polymeric product. Published erroneous NMR assignment of 4dthrHexp4enA C5 (14.3) was corrected (143.3) by authors
Related record ID(s): 3158, 3229, 3230
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
5,2,3,2,2 Ac
5,2,3,2 bDGlcpN 100.0 55.7 81.1 69.2 76.6 61.4
5,2,3,6 xLAla? 180.1 51.6 18.2
5,2,3 aL4dthrHexp4enA 99.5 75.7 62.3 106.6 143.3 ?
5,2,2 Ac
5,2 aDGlcpN 97.6 53.5 81.1 68.8 73.4 62.4
5 bDGalf 106.6 87.6 76.0 82.8 70.9 63.7
bDGalf 109.0 82.1 77.3 82.6 77.0 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
5,2,3,2,2 Ac
5,2,3,2 bDGlcpN 4.75 3.69 3.69 3.51 3.51 3.81-3.93
5,2,3,6 xLAla? - 4.25 1.36
5,2,3 aL4dthrHexp4enA 5.46 4.00 4.06 6.07 - -
5,2,2 Ac
5,2 aDGlcpN 5.02 4.14 3.98 3.53 3.84 3.80-3.87
5 bDGalf 5.28 4.18 4.26 4.08 3.88 3.7
bDGalf 5.02 4.02 4.08 4.13 3.95 3.75
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
5,2,3,2,2 Ac
5,2,3,2 bDGlcpN 100.0/4.75 55.7/3.69 81.1/3.69 69.2/3.51 76.6/3.51 61.4/3.81-3.93
5,2,3,6 xLAla? 51.6/4.25 18.2/1.36
5,2,3 aL4dthrHexp4enA 99.5/5.46 75.7/4.00 62.3/4.06 106.6/6.07
5,2,2 Ac
5,2 aDGlcpN 97.6/5.02 53.5/4.14 81.1/3.98 68.8/3.53 73.4/3.84 62.4/3.80-3.87
5 bDGalf 106.6/5.28 87.6/4.18 76.0/4.26 82.8/4.08 70.9/3.88 63.7/3.7
bDGalf 109.0/5.02 82.1/4.02 77.3/4.08 82.6/4.13 77.0/3.95 62.4/3.75
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 5,2,3,2,2 | Ac | |
| 5,2,3,2 | bDGlcpN | 4.75 | 3.69 | 3.69 | 3.51 | 3.51 | 3.81
3.93 |
| 5,2,3,6 | xLAla? |
| 4.25 | 1.36 | |
| 5,2,3 | aL4dthrHexp4enA | 5.46 | 4.00 | 4.06 | 6.07 |
|
|
| 5,2,2 | Ac | |
| 5,2 | aDGlcpN | 5.02 | 4.14 | 3.98 | 3.53 | 3.84 | 3.80
3.87 |
| 5 | bDGalf | 5.28 | 4.18 | 4.26 | 4.08 | 3.88 | 3.7 |
| | bDGalf | 5.02 | 4.02 | 4.08 | 4.13 | 3.95 | 3.75 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 5,2,3,2,2 | Ac | |
| 5,2,3,2 | bDGlcpN | 100.0 | 55.7 | 81.1 | 69.2 | 76.6 | 61.4 |
| 5,2,3,6 | xLAla? | 180.1 | 51.6 | 18.2 | |
| 5,2,3 | aL4dthrHexp4enA | 99.5 | 75.7 | 62.3 | 106.6 | 143.3 | ? |
| 5,2,2 | Ac | |
| 5,2 | aDGlcpN | 97.6 | 53.5 | 81.1 | 68.8 | 73.4 | 62.4 |
| 5 | bDGalf | 106.6 | 87.6 | 76.0 | 82.8 | 70.9 | 63.7 |
| | bDGalf | 109.0 | 82.1 | 77.3 | 82.6 | 77.0 | 62.4 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":100,"l":"1","c":[0,0,225]},{"s":55.7,"l":"2","c":[0,0,225]},{"s":81.1,"l":"3","c":[0,0,225]},{"s":69.2,"l":"4","c":[0,0,225]},{"s":76.6,"l":"5","c":[0,0,225]},{"s":61.4,"l":"6","c":[0,0,225]},{"s":180.1,"l":"1","c":[230,0,30]},{"s":51.6,"l":"2","c":[230,0,30]},{"s":18.2,"l":"3","c":[230,0,30]},{"s":99.5,"l":"1","c":[0,165,0]},{"s":75.7,"l":"2","c":[0,165,0]},{"s":62.3,"l":"3","c":[0,165,0]},{"s":106.6,"l":"4","c":[0,165,0]},{"s":143.3,"l":"5","c":[0,165,0]},{"s":97.6,"l":"1","c":[120,0,225]},{"s":53.5,"l":"2","c":[120,0,225]},{"s":81.1,"l":"3","c":[120,0,225]},{"s":68.8,"l":"4","c":[120,0,225]},{"s":73.4,"l":"5","c":[120,0,225]},{"s":62.4,"l":"6","c":[120,0,225]},{"s":106.6,"l":"1","c":[0,192,255]},{"s":87.6,"l":"2","c":[0,192,255]},{"s":76,"l":"3","c":[0,192,255]},{"s":82.8,"l":"4","c":[0,192,255]},{"s":70.9,"l":"5","c":[0,192,255]},{"s":63.7,"l":"6","c":[0,192,255]},{"s":109,"l":"1","c":[220,0,180]},{"s":82.1,"l":"2","c":[220,0,180]},{"s":77.3,"l":"3","c":[220,0,180]},{"s":82.6,"l":"4","c":[220,0,180]},{"s":77,"l":"5","c":[220,0,180]},{"s":62.4,"l":"6","c":[220,0,180]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
