Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
hemorrhagic colitis (HC) [ICD11:
1A40.0 ];
hemolytic-uremic syndrome (HUS) [ICD11:
3A21.2 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 22713129Publication DOI: 10.1021/jo300299pJournal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: pozsgayv
mail.nih.gov
Institutions: Program on Developmental and Molecular Immunity, Eunice Kennedy Shriver National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD, USA-2423, USA
Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colitis, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide of this bacterium is considered both a virulence factor and a protective antigen. It is built up of the linear tetrasaccharide repeating unit [3)-α-L-Rhap-(1→2)-α-D-Glcp-(1→3)-α-D-GlcNAcp-(1→3)-α-L-Rhap-(1→] differing from that of the O-SP of Shigella dysenteriae type 1 (SD) only in that the latter contains a d-Galp residue in place of the glucose moiety of the former. The close similarity of the O-SPs of these bacteria indicated a possible cross-reactivity. To answer this question we synthesized several oligosaccharide fragments of E. coli O148 O-SP, up to a dodecasaccharide, as well as their bovine serum albumin or recombinant diphtheria toxin conjugates. Immunization of mice with these conjugates induced anti-O-SP-specific serum IgG antibody responses. The antisera reacted equally well with the LPSs of both bacteria, indicating cross-reactivity between the SD and E. coli O148 O-SPs that was further supported by Western-blot and dot-blot analyses, as well as by inhibition of binding between the antisera and the O-SPs of both bacteria.
Escherichia coli, polysaccharide antigen, synthetic oligosaccharides
Structure type: oligomer
Location inside paper: p.5923, fig.1, 4, fig.3, 42
Aglycon: 5-{2-[(5′-Oxohexanoyl)amino]ethyl-amino}carbonylpentyl, methoxycarbonylpentyl, BSA
Contained glycoepitopes: IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, ESI-MS, Western blotting, MALDI-TOF MS, NMR-1D, serological methods, glycosylation, conjugatation
Synthetic data: chemical
Comments, role: NMR data for octasaccharide 42 with methoxycarbonylpentyl spacer.
Related record ID(s): 27289, 28591, 28592, 28593, 28594, 28596, 28597, 28598, 28599, 28600, 28601, 28602, 28603
NCBI Taxonomy refs (TaxIDs): 2162917Reference(s) to other database(s): GTC:G73238KZ
Show glycosyltransferases
NMR conditions: in vol 80%D2O / vol 20%(CD3)2CO at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2,3,3,3,2 aLRhap 102.26 70.65 70.87 72.68 69.95 17.58
3,3,2,3,3,3 aDGlcp 98.47 77.12 73.18 70.07 72.99 61.08
3,3,2,3,3,2 Ac 174.49 22.95
3,3,2,3,3 aDGlcpN 94.88 52.67 75.82 71.87 72.63 60.95
3,3,2,3 aLRhap 102.73 67.49 75.67 71.08 69.99 17.68
3,3,2 aLRhap 102.14 70.37 78.90 72.01 69.99 17.47
3,3 aDGlcp 98.47 77.30 73.33 69.99 72.99 61.08
3,2 Ac 174.58 22.93
3 aDGlcpN 94.98 52.66 76.22 71.87 72.55 60.86
aLRhap 100.32 67.54 76.01 71.03 69.39 17.53
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2,3,3,3,2 aLRhap 5.127 4.077 3.802 3.490 3.857 1.303
3,3,2,3,3,3 aDGlcp 5.564 3.662 3.754 3.486 3.658 3.796-3.868
3,3,2,3,3,2 Ac - 2.061
3,3,2,3,3 aDGlcpN 5.038 4.140 4.081 3.794 4.053 3.804-3.845
3,3,2,3 aLRhap 5.123 4.247 3.968 3.576 3.915 1.349
3,3,2 aLRhap 5.103 4.182 3.886 3.572 3.901 1.303
3,3 aDGlcp 5.564 3.662 3.754 3.488 3.658 3.876-3.976
3,2 Ac - 2.053
3 aDGlcpN 4.980 4.136 4.067 3.803 4.041 3.841-3.841
aLRhap 4.801 4.066 3.825 3.547 3.717 1.314
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2,3,3,3,2 aLRhap 102.26/5.127 70.65/4.077 70.87/3.802 72.68/3.490 69.95/3.857 17.58/1.303
3,3,2,3,3,3 aDGlcp 98.47/5.564 77.12/3.662 73.18/3.754 70.07/3.486 72.99/3.658 61.08/3.796-3.868
3,3,2,3,3,2 Ac 22.95/2.061
3,3,2,3,3 aDGlcpN 94.88/5.038 52.67/4.140 75.82/4.081 71.87/3.794 72.63/4.053 60.95/3.804-3.845
3,3,2,3 aLRhap 102.73/5.123 67.49/4.247 75.67/3.968 71.08/3.576 69.99/3.915 17.68/1.349
3,3,2 aLRhap 102.14/5.103 70.37/4.182 78.90/3.886 72.01/3.572 69.99/3.901 17.47/1.303
3,3 aDGlcp 98.47/5.564 77.30/3.662 73.33/3.754 69.99/3.488 72.99/3.658 61.08/3.876-3.976
3,2 Ac 22.93/2.053
3 aDGlcpN 94.98/4.980 52.66/4.136 76.22/4.067 71.87/3.803 72.55/4.041 60.86/3.841-3.841
aLRhap 100.32/4.801 67.54/4.066 76.01/3.825 71.03/3.547 69.39/3.717 17.53/1.314
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2,3,3,3,2 | aLRhap | 5.127 | 4.077 | 3.802 | 3.490 | 3.857 | 1.303 |
| 3,3,2,3,3,3 | aDGlcp | 5.564 | 3.662 | 3.754 | 3.486 | 3.658 | 3.796
3.868 |
| 3,3,2,3,3,2 | Ac |
| 2.061 | |
| 3,3,2,3,3 | aDGlcpN | 5.038 | 4.140 | 4.081 | 3.794 | 4.053 | 3.804
3.845 |
| 3,3,2,3 | aLRhap | 5.123 | 4.247 | 3.968 | 3.576 | 3.915 | 1.349 |
| 3,3,2 | aLRhap | 5.103 | 4.182 | 3.886 | 3.572 | 3.901 | 1.303 |
| 3,3 | aDGlcp | 5.564 | 3.662 | 3.754 | 3.488 | 3.658 | 3.876
3.976 |
| 3,2 | Ac |
| 2.053 | |
| 3 | aDGlcpN | 4.980 | 4.136 | 4.067 | 3.803 | 4.041 | 3.841
3.841 |
| | aLRhap | 4.801 | 4.066 | 3.825 | 3.547 | 3.717 | 1.314 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2,3,3,3,2 | aLRhap | 102.26 | 70.65 | 70.87 | 72.68 | 69.95 | 17.58 |
| 3,3,2,3,3,3 | aDGlcp | 98.47 | 77.12 | 73.18 | 70.07 | 72.99 | 61.08 |
| 3,3,2,3,3,2 | Ac | 174.49 | 22.95 | |
| 3,3,2,3,3 | aDGlcpN | 94.88 | 52.67 | 75.82 | 71.87 | 72.63 | 60.95 |
| 3,3,2,3 | aLRhap | 102.73 | 67.49 | 75.67 | 71.08 | 69.99 | 17.68 |
| 3,3,2 | aLRhap | 102.14 | 70.37 | 78.90 | 72.01 | 69.99 | 17.47 |
| 3,3 | aDGlcp | 98.47 | 77.30 | 73.33 | 69.99 | 72.99 | 61.08 |
| 3,2 | Ac | 174.58 | 22.93 | |
| 3 | aDGlcpN | 94.98 | 52.66 | 76.22 | 71.87 | 72.55 | 60.86 |
| | aLRhap | 100.32 | 67.54 | 76.01 | 71.03 | 69.39 | 17.53 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
