Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 16949062Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: malcolm.perry
nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada K1A OR6
The structure of the antigenic O-polysaccharide (O-PS) of the lipopolysaccharide (LPS) produced by the enterohemorrhagic strain of Escherichia coli O48:H21 (EHEC) has been elucidated. The O-PS obtained by mild acid hydrolysis of the LPS had [α]D +95 (water) and was composed of L-rhamnose (L-Rha), D-galactose (D-Gal), 2-amino-2-deoxy-D-glucose (D-GlcN), 2-amino-2-deoxy-D-galactose (D-GalN), and D-galacturonic acid (D-GalA) (1:1:1:1:1). From the results of methylation analysis, mass spectrometry, 2D NMR, and DOC-PAGE, the O-PS was shown to be a high molecular mass polymer of a repeating pentasaccharide unit having the structure: [structure: see text]. The D-GalpA non-reducing end groups in the O-PS were partially O-acetylated (approximately 30%) at the O-2 and O-3 positions and the degree of acetylation was variable from batch to batch cell production.
polysaccharide, Escherichia coli O48, LPS O-antigen
Structure type: polymer chemical repeating unit
Location inside paper: p.2543,abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_21,SB_7
Methods: methylation, NMR-2D, DOC-PAGE, MS
Biological activity: O-acetylation of the GalpA residue is ~30%
Comments, role: NMR data of the O-deacelated O-PS
Related record ID(s): 20366
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G24298SE, GlycomeDB:
27868
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3,4,2 Ac
4,3,4 bDGlcpN 102 56.1 83.1 69.3 76.6 61.6
4,3,2 Ac
4,3,3,2 Ac
4,3,3,3 Ac
4,3,3 aDGalpA 96.3 68.5 70.5 71.5 73.1 176.1
4,3 bDGalpN 103.8 51.9 75.8 73.5 74.5 61.6
4 aDGalp 100.8 68.3 79.6 70.0 70.9 61.8
aLRhap 102.1 71.8 69.8 81.5 68.9 17.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3,4,2 Ac
4,3,4 bDGlcpN 4.86 3.89 3.45 3.53 3.43 3.8-3.9
4,3,2 Ac
4,3,3,2 Ac
4,3,3,3 Ac
4,3,3 aDGalpA 5.23 4.01 3.85 4.31 4.25 -
4,3 bDGalpN 4.65 3.97 3.95 4.35 3.67 3.76-3.8
4 aDGalp 5.02 3.88 3.89 4.18 4.28 3.70
aLRhap 4.85 3.80 3.84 3.48 4.10 1.30
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3,4,2 Ac
4,3,4 bDGlcpN 102/4.86 56.1/3.89 83.1/3.45 69.3/3.53 76.6/3.43 61.6/3.8-3.9
4,3,2 Ac
4,3,3,2 Ac
4,3,3,3 Ac
4,3,3 aDGalpA 96.3/5.23 68.5/4.01 70.5/3.85 71.5/4.31 73.1/4.25
4,3 bDGalpN 103.8/4.65 51.9/3.97 75.8/3.95 73.5/4.35 74.5/3.67 61.6/3.76-3.8
4 aDGalp 100.8/5.02 68.3/3.88 79.6/3.89 70.0/4.18 70.9/4.28 61.8/3.70
aLRhap 102.1/4.85 71.8/3.80 69.8/3.84 81.5/3.48 68.9/4.10 17.6/1.30
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,3,4,2 | Ac | |
| 4,3,4 | bDGlcpN | 4.86 | 3.89 | 3.45 | 3.53 | 3.43 | 3.8
3.9 |
| 4,3,2 | Ac | |
| 4,3,3,2 | Ac | |
| 4,3,3,3 | Ac | |
| 4,3,3 | aDGalpA | 5.23 | 4.01 | 3.85 | 4.31 | 4.25 |
|
| 4,3 | bDGalpN | 4.65 | 3.97 | 3.95 | 4.35 | 3.67 | 3.76
3.8 |
| 4 | aDGalp | 5.02 | 3.88 | 3.89 | 4.18 | 4.28 | 3.70 |
| | aLRhap | 4.85 | 3.80 | 3.84 | 3.48 | 4.10 | 1.30 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3,4,2 | Ac | |
| 4,3,4 | bDGlcpN | 102 | 56.1 | 83.1 | 69.3 | 76.6 | 61.6 |
| 4,3,2 | Ac | |
| 4,3,3,2 | Ac | |
| 4,3,3,3 | Ac | |
| 4,3,3 | aDGalpA | 96.3 | 68.5 | 70.5 | 71.5 | 73.1 | 176.1 |
| 4,3 | bDGalpN | 103.8 | 51.9 | 75.8 | 73.5 | 74.5 | 61.6 |
| 4 | aDGalp | 100.8 | 68.3 | 79.6 | 70.0 | 70.9 | 61.8 |
| | aLRhap | 102.1 | 71.8 | 69.8 | 81.5 | 68.9 | 17.6 |
|
There is only one chemically distinct structure:
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