Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: hemolytic-uremic syndrome (HUS) [ICD11:
3A21.2 
];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 26582605Publication DOI: 10.1093/glycob/cwv106Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: goran.widmalm
su.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Laboratory Medicine, Division of Clinical Microbiology, Karolinska Institute, Karolinska University Hospital, Stockholm, Sweden, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China
Upon mild acid degradation of the lipopolysaccharide of Escherichia coli O165, the O-polysaccharide chain was cleaved at the glycosidic linkage of 5-N-acetyl-7-N-[(R)-3-hydroxybutanoyl]pseudaminic acid (Pse5Hb7Ac). Analysis of the resulting linear tetrasaccharide and alkali-treated lipopolysaccharide by 1H/13C 1D and 2D NMR spectroscopy enabled elucidation of the following structure of the O-polysaccharide:→8)-α-Psep5Hb7Ac-(2→6)-β-d-Galp-(1→4)-β-d-Glcp-(1→3)-α-d-GlcpNAc-(1→The β-d-Galp-(1→4)-β-d-Glcp-(1→3)-d-GlcpNAc structural element is also present in the O-polysaccharide of E. coli O82. The content of the O-antigen gene cluster of E. coli O165 was found to be consistent with the O-polysaccharide structure established. Functions of proteins encoded in the gene cluster, including enzymes involved in the Pse5Hb7Ac biosynthesis and glycosyltransferases, were putatively assigned by comparison with sequences in available databases.
Lipopolysaccharide, Escherichia coli, bacterial polysaccharide structure, O-antigen gene cluster
Structure type: oligomer
Location inside paper: table 5, oligosaccharide 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136044,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, GLC, mild acid hydrolysis, composition analysis, mild alkaline degradation, NMR-1D, GPC, bioinformatic analysis
Biosynthesis and genetic data: genetic data
Comments, role: Mild acid hydrolysis of the LPS.
Related record ID(s): 30669, 30858
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
NMR conditions: in 90%H2O / 10%D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
5 lR3HOBut 175.9 46.2 66.4 23.4
7 Ac 174.6 23.5
8,3,4 bDGalp 104.2 72.2 73.8 69.8 76.1 62.3
8,3 bDGlcp 104.0 74.0 75.4 79.5 76.1 61.3
8,2 Ac 175.6 23.3
8 aDGlcpN 96.0 53.8 81.7 69.8 73.1 61.7
aXPsep 177.4 97.7 36.2 66.8 50.1 70.7 53.8 73.8 13.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
5 lR3HOBut - 2.42-2.46 4.22 1.25
7 Ac - 1.99
8,3,4 bDGalp 4.45 3.55 3.67 3.93 3.63 3.75-3.78
8,3 bDGlcp 4.54 3.34 3.66 3.68 3.73 3.82-3.98
8,2 Ac - 2.02
8 aDGlcpN 4.96 4.06 3.85 3.58 3.89 3.83-3.85
aXPsep - - 1.82-1.92 4.16 4.30 4.07 4.19 4.06 1.11
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
5 lR3HOBut 46.2/2.42-2.46 66.4/4.22 23.4/1.25
7 Ac 23.5/1.99
8,3,4 bDGalp 104.2/4.45 72.2/3.55 73.8/3.67 69.8/3.93 76.1/3.63 62.3/3.75-3.78
8,3 bDGlcp 104.0/4.54 74.0/3.34 75.4/3.66 79.5/3.68 76.1/3.73 61.3/3.82-3.98
8,2 Ac 23.3/2.02
8 aDGlcpN 96.0/4.96 53.8/4.06 81.7/3.85 69.8/3.58 73.1/3.89 61.7/3.83-3.85
aXPsep 36.2/1.82-1.92 66.8/4.16 50.1/4.30 70.7/4.07 53.8/4.19 73.8/4.06 13.8/1.11
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 5 | lR3HOBut |
| 2.42
2.46 | 4.22 | 1.25 | |
| 7 | Ac |
| 1.99 | |
| 8,3,4 | bDGalp | 4.45 | 3.55 | 3.67 | 3.93 | 3.63 | 3.75
3.78 | |
| 8,3 | bDGlcp | 4.54 | 3.34 | 3.66 | 3.68 | 3.73 | 3.82
3.98 | |
| 8,2 | Ac |
| 2.02 | |
| 8 | aDGlcpN | 4.96 | 4.06 | 3.85 | 3.58 | 3.89 | 3.83
3.85 | |
| | aXPsep |
|
| 1.82
1.92 | 4.16 | 4.30 | 4.07 | 4.19 | 4.06 | 1.11 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 5 | lR3HOBut | 175.9 | 46.2 | 66.4 | 23.4 | |
| 7 | Ac | 174.6 | 23.5 | |
| 8,3,4 | bDGalp | 104.2 | 72.2 | 73.8 | 69.8 | 76.1 | 62.3 | |
| 8,3 | bDGlcp | 104.0 | 74.0 | 75.4 | 79.5 | 76.1 | 61.3 | |
| 8,2 | Ac | 175.6 | 23.3 | |
| 8 | aDGlcpN | 96.0 | 53.8 | 81.7 | 69.8 | 73.1 | 61.7 | |
| | aXPsep | 177.4 | 97.7 | 36.2 | 66.8 | 50.1 | 70.7 | 53.8 | 73.8 | 13.8 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
