Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Shigella dysenteriae [ICD11:
XN285 
];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 17185542Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: wanglei
nankai.edu.cn
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, 23 HongDa Street,TEDA, Tianjin 300457, P. R. China,Tianjin Key Laboratory for Microbial Functional Genomics, Nankai University, 23 HongDa Street, TEDA, Tianjin 300457, P. R. China, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, College of Life Sciences, Nankai University, Tianjin 300071, P. R. China,School of Molecular and Microbial Biosciences (G08), University of Sydney, Sydney, NSW 2006, Australia
Shigella dysenteriae type 1 is the most virulent serotype of Shigella. Enterotoxigenic Escherichia coli O148 is pathogenic and can cause diarrhoea. The following structure was established for the tetrasaccharide repeating unit of the E. coli O148 O antigen: R3)-a-L-Rhap-(1R3)-a-L-Rhap-(1R2)-a-D-Glcp-(1R3)-a-D-GlcpNAc-(1R. This differs from the structure reported earlier for S. dysenteriae type 1 by having a glucose (Glc) residue in place of a galactose (Gal) residue. The two bacteria also have the same genes for O antigen synthesis, with the same organization and high level of DNA identity, except that in S. dysenteriae type 1 wbbG is interrupted by a deletion, and a galactosyltransferase gene wbbP located on a plasmid is responsible for the transfer of galactose to make a novel antigenic epitope of the O antigen. The S. dysenteriae type 1 O antigen was reconstructed by replacing the E. coli O148 wbbG gene with the wbbP gene, and it had the LPS structure and antigenic properties of S. dysenteriae type 1,indicating that the S. dysenteriae type 1 O antigen evolved from that of E. coli O148. It was also confirmed that wbbG of E. coli O148 is a glucosyltransferase gene, and two serotype-specific genes of E. coli O148 and S. dysenteriae type 1 were identified.
NMR, antigen, gene, O-antigen, type, Shigella dysenteriae type 1, glucosyltransferase, Escherichia coli O148, chloramphenicol acetyltransferase
Structure type: polymer chemical repeating unit
Location inside paper: p.143, fig.2
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125611,IEDB_130668,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137483,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, mild acid hydrolysis, NMR-1D, serological methods, genetic methods
Biological activity: serological data
Biosynthesis and genetic data: genetic data
Related record ID(s): 2158, 3227, 3783, 6263, 6843, 7715, 20113, 21578, 23061, 124115, 130504
NCBI Taxonomy refs (TaxIDs): 984897,
622Reference(s) to other database(s): GTC:G76746EO, GlycomeDB:
6223
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,3 aLRhap 103.4 68.1 76.4 71.8 70.8 18.3
3,2 aLRhap 102.8 71.0 79.5 72.7 70.6 18.1
3 aDGalp 99.1 75.2 70.5 70.9 72.3 62.2
2 Ac 175.5 23.6
aDGlcpN 95.6 53.4 76.3 72.6 73.3 61.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,3 aLRhap 5.10 4.22 3.93 3.55 3.90 1.33
3,2 aLRhap 5.05 4.16 3.87 3.56 3.90 1.29
3 aDGalp 5.59 3.93 3.88 4.01 3.92 3.77
2 Ac - 2.07
aDGlcpN 5.03 4.13 4.08 3.78 4.20 3.82
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,3 aLRhap 103.4/5.10 68.1/4.22 76.4/3.93 71.8/3.55 70.8/3.90 18.3/1.33
3,2 aLRhap 102.8/5.05 71.0/4.16 79.5/3.87 72.7/3.56 70.6/3.90 18.1/1.29
3 aDGalp 99.1/5.59 75.2/3.93 70.5/3.88 70.9/4.01 72.3/3.92 62.2/3.77
2 Ac 23.6/2.07
aDGlcpN 95.6/5.03 53.4/4.13 76.3/4.08 72.6/3.78 73.3/4.20 61.6/3.82
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,3 | aLRhap | 5.10 | 4.22 | 3.93 | 3.55 | 3.90 | 1.33 |
| 3,2 | aLRhap | 5.05 | 4.16 | 3.87 | 3.56 | 3.90 | 1.29 |
| 3 | aDGalp | 5.59 | 3.93 | 3.88 | 4.01 | 3.92 | 3.77 |
| 2 | Ac |
| 2.07 | |
| | aDGlcpN | 5.03 | 4.13 | 4.08 | 3.78 | 4.20 | 3.82 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,3 | aLRhap | 103.4 | 68.1 | 76.4 | 71.8 | 70.8 | 18.3 |
| 3,2 | aLRhap | 102.8 | 71.0 | 79.5 | 72.7 | 70.6 | 18.1 |
| 3 | aDGalp | 99.1 | 75.2 | 70.5 | 70.9 | 72.3 | 62.2 |
| 2 | Ac | 175.5 | 23.6 | |
| | aDGlcpN | 95.6 | 53.4 | 76.3 | 72.6 | 73.3 | 61.6 |
|
There is only one chemically distinct structure:
Found 
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