Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: G. Widmalm <gw
organ.su.se>
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Karolinska Institute, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge University Hospital, Sweden
The structure of the O-antigen polysaccharide from Escherichia coli O159 has been determined using primarily NMR spectroscopy of the 13C-enriched polysaccharide. The sequence of the sugar residues could be determined by heteronuclear multiple bond connectivity NMR experiments. The polysaccharide is composed of a pentasaccharide repeating unit with the following structure: [see structure in text]. Matrix assisted laser desorption ionization mass spectrometry was performed on intact lipopolysaccharide and from the resulting molecular mass the O-antigen part was estimated to contain approximately 23 repeating units. Cross-reactivity of this O-antigen to that of Shigella dysenteriae type 4 was confirmed using enzyme-linked immunoabsorbant assay.
structural, polysaccharide, O-antigen, O antigen, Escherichia, Escherichia coli, enterotoxigenic, type, structural studies, Shigella, Shigella dysenteriae
Structure type: suggested polymer biological repeating unit ; 25000, n=~23
Location inside paper: abstract
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_423096,SB_86
Methods: NMR-2D, methylation, NMR, sugar analysis, MALDI-MS, determination of absolute configuration
Biological activity: serological activity data
Related record ID(s): 9411, 11788, 20692, 21741, 23067, 23214, 25693
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G18063HY, GlycomeDB:
25912
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,3 aDGalpA 101.2 69.7 70.6 80.2 72.4 175.7
3,3 aLFucp 100.1 67.9 78.5 72.5 67.7 15.8
3,2 Ac
3 bDGlcpN 102.8 57.0 76.9 73.8 76.0 61.5
2 Ac
4 aLFucp 98.6 68.7 70.0 72.8 67.4 16.3
bDGlcpN 100.8 56.7 80.5 70.5 76.4 62.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,3 aDGalpA 5.19 3.70 4.03 4.35 4.33 -
3,3 aLFucp 4.99 3.84 3.89 3.84 4.28 1.12
3,2 Ac
3 bDGlcpN 4.59 3.81 4.04 3.63 3.43 3.74-3.93
2 Ac
4 aLFucp 4.94 3.81 3.92 3.80 4.71 1.26
bDGlcpN 4.74 3.60 3.84 3.30 3.41 3.59-3.96
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,3 aDGalpA 101.2/5.19 69.7/3.70 70.6/4.03 80.2/4.35 72.4/4.33
3,3 aLFucp 100.1/4.99 67.9/3.84 78.5/3.89 72.5/3.84 67.7/4.28 15.8/1.12
3,2 Ac
3 bDGlcpN 102.8/4.59 57.0/3.81 76.9/4.04 73.8/3.63 76.0/3.43 61.5/3.74-3.93
2 Ac
4 aLFucp 98.6/4.94 68.7/3.81 70.0/3.92 72.8/3.80 67.4/4.71 16.3/1.26
bDGlcpN 100.8/4.74 56.7/3.60 80.5/3.84 70.5/3.30 76.4/3.41 62.5/3.59-3.96
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,3 | aDGalpA | 5.19 | 3.70 | 4.03 | 4.35 | 4.33 |
|
| 3,3 | aLFucp | 4.99 | 3.84 | 3.89 | 3.84 | 4.28 | 1.12 |
| 3,2 | Ac | |
| 3 | bDGlcpN | 4.59 | 3.81 | 4.04 | 3.63 | 3.43 | 3.74
3.93 |
| 2 | Ac | |
| 4 | aLFucp | 4.94 | 3.81 | 3.92 | 3.80 | 4.71 | 1.26 |
| | bDGlcpN | 4.74 | 3.60 | 3.84 | 3.30 | 3.41 | 3.59
3.96 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,3 | aDGalpA | 101.2 | 69.7 | 70.6 | 80.2 | 72.4 | 175.7 |
| 3,3 | aLFucp | 100.1 | 67.9 | 78.5 | 72.5 | 67.7 | 15.8 |
| 3,2 | Ac | |
| 3 | bDGlcpN | 102.8 | 57.0 | 76.9 | 73.8 | 76.0 | 61.5 |
| 2 | Ac | |
| 4 | aLFucp | 98.6 | 68.7 | 70.0 | 72.8 | 67.4 | 16.3 |
| | bDGlcpN | 100.8 | 56.7 | 80.5 | 70.5 | 76.4 | 62.5 |
|
There is only one chemically distinct structure:
Found 
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