Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 10561586Publication DOI: 10.1046/j.1432-1327.1999.00878.xJournal 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 O164 has been determined. Nuclear magnetic resonance spectroscopy together with component and methylation analyses of lipid free polysaccharide were the principal methods used. The sequence of the sugar residues could be determined by NOESY and heteronuclear multiple bond connectivity NMR experiments. It is concluded that the polysaccharide is composed of a pentasaccharide repeating unit with the following structure: [see structure in text]. Matrix assisted laser desorption ionization mass spectrometry (MALDI-MS) was performed on intact lipopolysaccharide and from the resulting molecular mass, the O-antigen part was estimated to contain approximately 24 repeating units. The nature of the previously reported cross-reactivity of this O-antigen to those of Escherichia coli O124 and Shigella dysenteriae type 3 is discussed.
structural, polysaccharide, O-antigen, O antigen, Escherichia, Escherichia coli, type, structural studies, Shigella, Shigella dysenteriae
Structure type: suggested polymer biological repeating unit ; 24000, n=24
Location inside paper: abstract
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_21,SB_7,SB_88
Methods: methylation, NMR-2D, NMR, sugar analysis, MS
Biological activity: serological actrivity data
Comments, role: chemical repeat frame is different in the paper
Related record ID(s): 11570, 20693, 23065, 23205
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G82779NI, GlycomeDB:
25911
Show glycosyltransferases
NMR conditions: in D2O at 318 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,6,4,6 bDGlcp 103.5 74.1 76.6 70.6 76.8 61.8
3,6,4 aDGlcp 100.0 72.9 73.6 69.7 71.5 68.9
3,6 bDGalp 104.4 71.8 81.6 76.4 76.2 60.7
3 bDGalf 110.0 82.2 78.0 84.2 70.5 72.2
2 Ac 175.3 23.2
bDGalpN 104.2 52.2 79.3 70.6 75.8 62.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,6,4,6 bDGlcp 4.50 3.35 3.52 3.42 3.46 3.73-3.93
3,6,4 aDGlcp 4.92 3.51 3.74 3.65 4.31 4.05-4.33
3,6 bDGalp 4.49 3.68 3.83 4.24 3.77 3.82-3.87
3 bDGalf 5.09 4.10 4.05 4.05 4.01 3.74-4.07
2 Ac - 2.06
bDGalpN 4.71 3.96 3.81 4.05 3.67 3.78-3.86
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,6,4,6 bDGlcp 103.5/4.50 74.1/3.35 76.6/3.52 70.6/3.42 76.8/3.46 61.8/3.73-3.93
3,6,4 aDGlcp 100.0/4.92 72.9/3.51 73.6/3.74 69.7/3.65 71.5/4.31 68.9/4.05-4.33
3,6 bDGalp 104.4/4.49 71.8/3.68 81.6/3.83 76.4/4.24 76.2/3.77 60.7/3.82-3.87
3 bDGalf 110.0/5.09 82.2/4.10 78.0/4.05 84.2/4.05 70.5/4.01 72.2/3.74-4.07
2 Ac 23.2/2.06
bDGalpN 104.2/4.71 52.2/3.96 79.3/3.81 70.6/4.05 75.8/3.67 62.0/3.78-3.86
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,6,4,6 | bDGlcp | 4.50 | 3.35 | 3.52 | 3.42 | 3.46 | 3.73
3.93 |
| 3,6,4 | aDGlcp | 4.92 | 3.51 | 3.74 | 3.65 | 4.31 | 4.05
4.33 |
| 3,6 | bDGalp | 4.49 | 3.68 | 3.83 | 4.24 | 3.77 | 3.82
3.87 |
| 3 | bDGalf | 5.09 | 4.10 | 4.05 | 4.05 | 4.01 | 3.74
4.07 |
| 2 | Ac |
| 2.06 | |
| | bDGalpN | 4.71 | 3.96 | 3.81 | 4.05 | 3.67 | 3.78
3.86 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,6,4,6 | bDGlcp | 103.5 | 74.1 | 76.6 | 70.6 | 76.8 | 61.8 |
| 3,6,4 | aDGlcp | 100.0 | 72.9 | 73.6 | 69.7 | 71.5 | 68.9 |
| 3,6 | bDGalp | 104.4 | 71.8 | 81.6 | 76.4 | 76.2 | 60.7 |
| 3 | bDGalf | 110.0 | 82.2 | 78.0 | 84.2 | 70.5 | 72.2 |
| 2 | Ac | 175.3 | 23.2 | |
| | bDGalpN | 104.2 | 52.2 | 79.3 | 70.6 | 75.8 | 62.0 |
|
There is only one chemically distinct structure:
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