Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 20555398Publication DOI: 10.1139/w10-015Journal NLM ID: 0372707Publisher: National Research Council of Canada
Correspondence: malcolm.perry
nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, 100 Sussex Drive, Ottawa, ON K1A 0R6, Canada
The structure of the antigenic O-polysaccharide isolated from the lipopolysaccharide produced by enterohemorrhagic Escherichia coli O103:H2 was determined and shown to be composed of d-glucose (1 part), 2-acetamido-2-deoxy-d-glucose (2 parts), 2-acetamido-2-deoxy-d-galactose (1 part), and 3-deoxy-3-(R)-3-hydroxybutyramido-d-fucose (1 part). From the results of methylation analysis, Smith-type periodate oxidation degradation studies, and the use of one- and two-dimensional (1)H and (13)C NMR spectroscopy, the O-polysaccharide antigen was found to be an unbranched polymer of a repeating pentasaccharide unit having the following structure: →2)-β-D-Glcp-(1→2)-β-D-Fucp3NBu-(1→6)-α-D-GlcpNAc-(1→4)-α-D-GalpNAc-(1→3)-β-D-GlcpNAc-(1→, where Bu is (R)-3-hydroxybutyramido.
lipopolysaccharides, structure, O-antigenic polysaccharide, NMR spectroscopy, enteropathogenic, Escherichia coli O103:H2
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.369, Scheme 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_885822,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, acid hydrolysis, GLC, DOC-PAGE, Smith degradation, NMR-1D
Related record ID(s): 25745, 25881, 25882
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,6,2 bDGlcp 101.5 82.7 77.5 71.4 77.3 62.0
3,4,6,3 lR3HOBut 175.0 46.2 66.2 23.5
3,4,6 bDFucp3N 103.9 74.5 55.9 71.7 73.1 16.6
3,4,2 Ac
3,4 aDGlcpN 99.5 55.3 71.6 70.4 72.4 69.2
3,2 Ac
3 aDGalpN 98.3 51.0 68.3 78.1 73.0 61.1
2 Ac
bDGlcpN 102.7 55.8 79.6 72.1 77.0 62.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,6,2 bDGlcp 4.70 3.46 3.48 3.39 3.39 3.75-3.92
3,4,6,3 lR3HOBut - 2.49 4.25 1.27
3,4,6 bDFucp3N 4.56 3.89 4.17 3.65 3.86 1.25
3,4,2 Ac
3,4 aDGlcpN 4.94 3.95 3.88 3.88 4.22 3.93-4.04
3,2 Ac
3 aDGalpN 5.50 4.27 3.91 4.06 3.92 3.71-3.75
2 Ac
bDGlcpN 4.81 3.76 3.75 3.69 3.40 3.75-3.92
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,6,2 bDGlcp 101.5/4.70 82.7/3.46 77.5/3.48 71.4/3.39 77.3/3.39 62.0/3.75-3.92
3,4,6,3 lR3HOBut 46.2/2.49 66.2/4.25 23.5/1.27
3,4,6 bDFucp3N 103.9/4.56 74.5/3.89 55.9/4.17 71.7/3.65 73.1/3.86 16.6/1.25
3,4,2 Ac
3,4 aDGlcpN 99.5/4.94 55.3/3.95 71.6/3.88 70.4/3.88 72.4/4.22 69.2/3.93-4.04
3,2 Ac
3 aDGalpN 98.3/5.50 51.0/4.27 68.3/3.91 78.1/4.06 73.0/3.92 61.1/3.71-3.75
2 Ac
bDGlcpN 102.7/4.81 55.8/3.76 79.6/3.75 72.1/3.69 77.0/3.40 62.3/3.75-3.92
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,6,2 | bDGlcp | 4.70 | 3.46 | 3.48 | 3.39 | 3.39 | 3.75
3.92 |
| 3,4,6,3 | lR3HOBut |
| 2.49 | 4.25 | 1.27 | |
| 3,4,6 | bDFucp3N | 4.56 | 3.89 | 4.17 | 3.65 | 3.86 | 1.25 |
| 3,4,2 | Ac | |
| 3,4 | aDGlcpN | 4.94 | 3.95 | 3.88 | 3.88 | 4.22 | 3.93
4.04 |
| 3,2 | Ac | |
| 3 | aDGalpN | 5.50 | 4.27 | 3.91 | 4.06 | 3.92 | 3.71
3.75 |
| 2 | Ac | |
| | bDGlcpN | 4.81 | 3.76 | 3.75 | 3.69 | 3.40 | 3.75
3.92 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,6,2 | bDGlcp | 101.5 | 82.7 | 77.5 | 71.4 | 77.3 | 62.0 |
| 3,4,6,3 | lR3HOBut | 175.0 | 46.2 | 66.2 | 23.5 | |
| 3,4,6 | bDFucp3N | 103.9 | 74.5 | 55.9 | 71.7 | 73.1 | 16.6 |
| 3,4,2 | Ac | |
| 3,4 | aDGlcpN | 99.5 | 55.3 | 71.6 | 70.4 | 72.4 | 69.2 |
| 3,2 | Ac | |
| 3 | aDGalpN | 98.3 | 51.0 | 68.3 | 78.1 | 73.0 | 61.1 |
| 2 | Ac | |
| | bDGlcpN | 102.7 | 55.8 | 79.6 | 72.1 | 77.0 | 62.3 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
