Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: bacillary dysentery (shigellosis) [ICD11:
1A02 
, ICD11:
SA56 , ICD11:
XN7HG ];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
The structure was elucidated in this paperNCBI PubMed ID: 23603189Publication DOI: 10.1016/j.carres.2013.03.015Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Perepelov <perepel
ioc.ac.ru>
Institutions: ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Recently, strains of a novel Shigella flexneri serotype called 1d have been isolated from diarrheal patients in China. They are distinguished by the presence of a hitherto unknown combination of type O-factor I and group O-factor 7,8, both associated with lateral ?-D-glucosyl groups on the basal linear O-polysaccharide. A serologically identical strain, 036_1d, has been constructed in the laboratory by sequential infection of serotype Y by serotype-converting bacteriophages SfX and SfI. In this work, using 1D and 2D (1)H and (13)C NMR spectroscopy, we established the following structure of the O-antigen of S. flexneri serotype 1d and demonstrated that the O-antigen of the 036_1d construct has the same structure: [structure: see text].
O-antigen, Shigella flexneri, serological classification, bacterial polysaccharide structure, Phage-encoded glucosylation
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.96, chart 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_158539,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, mild acid hydrolysis, de-O-acetylation, NMR-1D, GPC
Comments, role: wild-type Shigella flexneri HN153 serotype 1d and a laboratory strain Shigella flexneri 036_1d
Related record ID(s): 29343
NCBI Taxonomy refs (TaxIDs): 623Reference(s) to other database(s): GTC:G17821WD
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2,3 aDGlcp 96.3 72.5 74.2 70.6 72.6 61.5
3,3,2 aLRhap 102.6 75.4 75.5 72.0 70.6 18.1
3,3 aLRhap 101.5 79.7 71.0 73.3 70.3 18.1
3 aLRhap 100.7 71.7 77.2 73.0 71.1 17.9
2 Ac 175.4 23.9
4 aDGlcp 97.8 72.4 73.9 70.4 73.8 61.6
bDGlcpN 102.9 56.0 81.6 71.8 76.6 62.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2,3 aDGlcp 5.15 3.69 3.81 3.49 4.02 3.79-3.81
3,3,2 aLRhap 5.10 4.40 3.91 3.36 3.72 1.25
3,3 aLRhap 5.23 4.05 3.93 3.47 3.73 1.31
3 aLRhap 5.11 3.92 3.79 3.58 3.78 1.27
2 Ac - 2.09
4 aDGlcp 5.46 3.57 3.66 3.43 3.61 3.76-3.85
bDGlcpN 4.39 3.95 4.01 3.96 3.66 3.79-3.88
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2,3 aDGlcp 96.3/5.15 72.5/3.69 74.2/3.81 70.6/3.49 72.6/4.02 61.5/3.79-3.81
3,3,2 aLRhap 102.6/5.10 75.4/4.40 75.5/3.91 72.0/3.36 70.6/3.72 18.1/1.25
3,3 aLRhap 101.5/5.23 79.7/4.05 71.0/3.93 73.3/3.47 70.3/3.73 18.1/1.31
3 aLRhap 100.7/5.11 71.7/3.92 77.2/3.79 73.0/3.58 71.1/3.78 17.9/1.27
2 Ac 23.9/2.09
4 aDGlcp 97.8/5.46 72.4/3.57 73.9/3.66 70.4/3.43 73.8/3.61 61.6/3.76-3.85
bDGlcpN 102.9/4.39 56.0/3.95 81.6/4.01 71.8/3.96 76.6/3.66 62.3/3.79-3.88
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2,3 | aDGlcp | 5.15 | 3.69 | 3.81 | 3.49 | 4.02 | 3.79
3.81 |
| 3,3,2 | aLRhap | 5.10 | 4.40 | 3.91 | 3.36 | 3.72 | 1.25 |
| 3,3 | aLRhap | 5.23 | 4.05 | 3.93 | 3.47 | 3.73 | 1.31 |
| 3 | aLRhap | 5.11 | 3.92 | 3.79 | 3.58 | 3.78 | 1.27 |
| 2 | Ac |
| 2.09 | |
| 4 | aDGlcp | 5.46 | 3.57 | 3.66 | 3.43 | 3.61 | 3.76
3.85 |
| | bDGlcpN | 4.39 | 3.95 | 4.01 | 3.96 | 3.66 | 3.79
3.88 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2,3 | aDGlcp | 96.3 | 72.5 | 74.2 | 70.6 | 72.6 | 61.5 |
| 3,3,2 | aLRhap | 102.6 | 75.4 | 75.5 | 72.0 | 70.6 | 18.1 |
| 3,3 | aLRhap | 101.5 | 79.7 | 71.0 | 73.3 | 70.3 | 18.1 |
| 3 | aLRhap | 100.7 | 71.7 | 77.2 | 73.0 | 71.1 | 17.9 |
| 2 | Ac | 175.4 | 23.9 | |
| 4 | aDGlcp | 97.8 | 72.4 | 73.9 | 70.4 | 73.8 | 61.6 |
| | bDGlcpN | 102.9 | 56.0 | 81.6 | 71.8 | 76.6 | 62.3 |
|
There is only one chemically distinct structure:
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