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: oligomer
Location inside paper: abstract, p.369, Scheme 1, I
Compound class: O-polysaccharide
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, acid hydrolysis, GLC, DOC-PAGE, Smith degradation, NMR-1D
Comments, role: O-polysaccharide upon Smith degradation. Published NMR assignment of Gro C2 (60.8) is erroneous in Table 2.
Related record ID(s): 25457, 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
1,3 lR3HOBut 175.0 44.9 65.2 22.1
1 bDFucp3N 103.8 68.6 54.9 70.2 72.1 15.1
x?Gro 71.1 ? 62.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1,3 lR3HOBut - 2.47 4.21 1.24
1 bDFucp3N 4.48 3.54 3.98 3.71 3.89 1.24
x?Gro 3.67-3.97 3.75 3.60-3.66
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1,3 lR3HOBut 44.9/2.47 65.2/4.21 22.1/1.24
1 bDFucp3N 103.8/4.48 68.6/3.54 54.9/3.98 70.2/3.71 72.1/3.89 15.1/1.24
x?Gro 71.1/3.67-3.97 ?/3.75 62.5/3.60-3.66
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1,3 | lR3HOBut |
| 2.47 | 4.21 | 1.24 | |
| 1 | bDFucp3N | 4.48 | 3.54 | 3.98 | 3.71 | 3.89 | 1.24 |
| | x?Gro | 3.67
3.97 | 3.75 | 3.60
3.66 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 1,3 | lR3HOBut | 175.0 | 44.9 | 65.2 | 22.1 | |
| 1 | bDFucp3N | 103.8 | 68.6 | 54.9 | 70.2 | 72.1 | 15.1 |
| | x?Gro | 71.1 | ? | 62.5 | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":175,"l":"1","c":[0,0,225]},{"s":44.9,"l":"2","c":[0,0,225]},{"s":65.2,"l":"3","c":[0,0,225]},{"s":22.1,"l":"4","c":[0,0,225]},{"s":103.8,"l":"1","c":[230,0,30]},{"s":68.6,"l":"2","c":[230,0,30]},{"s":54.9,"l":"3","c":[230,0,30]},{"s":70.2,"l":"4","c":[230,0,30]},{"s":72.1,"l":"5","c":[230,0,30]},{"s":15.1,"l":"6","c":[230,0,30]},{"s":71.1,"l":"1","c":[0,165,0]},{"s":62.5,"l":"3","c":[0,165,0]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Found 
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