Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 10231364Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: gw+AEA-organ.su.se
Institutions: Department of Organic Chemistry, Stockholm University, Sweden, Karolinska Institute, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Huddinge University Hospital, Sweden, Department of Chemistry and Physiological Sciences, Universidad National Autonoma de Nicaragua, UNAN-Leon, Nicaragua
The O-antigen polysaccharide of the lipopolysaccharide from the enteroaggregative Escherichia coli strain 62D1 has been determined. Sugar and methylation analysis together with 1H and 13C NMR spectroscopy revealed the components of the repeating unit. Two-dimensional NOESY and heteronuclear multiple-bond correlation experiments were used to deduce the sequence. 1H and 13C NMR spectra indicate heterogeneity in the polysaccharide. Methylation analysis and 1H NMR spectra of native and Smith-degraded material show that the majority (65+ACU-) of the repeating units has the following structure: Minor resonances in the NMR spectra are consistent with the presence of repeating units which lack the α-D-Galp terminal residue (35+ACU-).
Lipopolysaccharide, NMR, LPS, structure, strain, structural, polysaccharide, O-antigen, Escherichia, Escherichia coli, O-antigenic, O-antigenic polysaccharide, structure elucidation, elucidation, Enteroaggregative, heterogeneity
Structure type: polymer chemical repeating unit
Location inside paper: abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_134624,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_742248,IEDB_885823,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: methylation, NMR-2D, NMR, Smith degradation
Comments, role: O-antigenic polysaccharide, the major repeating unit (ca. 65+ACU-)
Related record ID(s): 20695
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G48195YB, GlycomeDB:
26492
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,3,3 Ac
3,3,3 bDQuip3N 104.8 75.1 56.6 73.7 73.7 17.7
3,3 aLRhap 102.9 70.5 80.6 71.6 70.1 17.5
3,6 aDGalp 99.5 69.0 70.2 70.1 72.0 62.0
3 bDGalp 105.7 70.7 81.5 69.0 73.4 67.0
2 Ac
aDFucpN 96.5 48.4 79.7 72.0 67.5 16.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,3,3 Ac
3,3,3 bDQuip3N 4.89 3.48 3.93 3.24 3.58 1.32
3,3 aLRhap 5.02 4.31 3.95 3.52 3.85 1.28
3,6 aDGalp 4.98 3.85 3.79 3.98 3.88 3.75
3 bDGalp 4.48 3.63 3.69 4.07 3.91 3.65-3.89
2 Ac
aDFucpN 5.56 4.33 3.74 3.99 3.96 1.27
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,3,3 Ac
3,3,3 bDQuip3N 104.8/4.89 75.1/3.48 56.6/3.93 73.7/3.24 73.7/3.58 17.7/1.32
3,3 aLRhap 102.9/5.02 70.5/4.31 80.6/3.95 71.6/3.52 70.1/3.85 17.5/1.28
3,6 aDGalp 99.5/4.98 69.0/3.85 70.2/3.79 70.1/3.98 72.0/3.88 62.0/3.75
3 bDGalp 105.7/4.48 70.7/3.63 81.5/3.69 69.0/4.07 73.4/3.91 67.0/3.65-3.89
2 Ac
aDFucpN 96.5/5.56 48.4/4.33 79.7/3.74 72.0/3.99 67.5/3.96 16.4/1.27
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,3,3 | Ac | |
| 3,3,3 | bDQuip3N | 4.89 | 3.48 | 3.93 | 3.24 | 3.58 | 1.32 |
| 3,3 | aLRhap | 5.02 | 4.31 | 3.95 | 3.52 | 3.85 | 1.28 |
| 3,6 | aDGalp | 4.98 | 3.85 | 3.79 | 3.98 | 3.88 | 3.75 |
| 3 | bDGalp | 4.48 | 3.63 | 3.69 | 4.07 | 3.91 | 3.65
3.89 |
| 2 | Ac | |
| | aDFucpN | 5.56 | 4.33 | 3.74 | 3.99 | 3.96 | 1.27 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,3,3 | Ac | |
| 3,3,3 | bDQuip3N | 104.8 | 75.1 | 56.6 | 73.7 | 73.7 | 17.7 |
| 3,3 | aLRhap | 102.9 | 70.5 | 80.6 | 71.6 | 70.1 | 17.5 |
| 3,6 | aDGalp | 99.5 | 69.0 | 70.2 | 70.1 | 72.0 | 62.0 |
| 3 | bDGalp | 105.7 | 70.7 | 81.5 | 69.0 | 73.4 | 67.0 |
| 2 | Ac | |
| | aDFucpN | 96.5 | 48.4 | 79.7 | 72.0 | 67.5 | 16.4 |
|
There is only one chemically distinct structure:
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