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: 22724405Publication DOI: 10.1111/j.1574-695X.2012.01000.xJournal NLM ID: 9315554Publisher: Elsevier
Correspondence: knirel
ioc.ac.ru
Institutions: N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Shigella flexneri is an important human pathogen causing shigellosis. Strains of S. flexneri are serologically heterogeneous and, based on O-antigens, are currently classified into 14 types. Structures of the O-antigens (O-polysaccharides) of S. flexneri have been under study since 1960s but some gaps still remained. In this work, using one- and two-dimensional (1) H- and (13) C-NMR spectroscopy, the O-polysaccharides of several S. flexneri types were reinvestigated, and their structures were either confirmed (types 2b, 3b, 3c, 5b, X) or amended in respect to the O-acetylation pattern (types 3a, Y, 6, 6a). As a result, the O-acetylation sites were defined in all O-polysaccharides that had not been studied in detail earlier, and the long story of S. flexneri type strain O-antigen structure elucidation is thus completed. New and published data on the S. flexneri O-antigen structures are summarized and discussed in view of serological and genetic relationships of the O-antigens within the Shigella group and between S. flexneri and Escherichia coli.
Shigella flexneri, O-acetylation, serological classification, O-Polysaccharide structure, O-antigen diversity
Structure type: polymer chemical repeating unit
Location inside paper: p.204, table 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_130687,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135806,IEDB_135807,IEDB_135808,IEDB_135809,IEDB_135813,IEDB_135817,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, ELISA, de-O-acetylation, NMR-1D, GPC
Comments, role: NMR temperature: 303-310
Related record ID(s): 27278, 28558, 28559, 28561, 28562, 28563, 28564, 28565, 28566, 28567, 28568, 28569, 28570, 28571, 28572, 28573, 28868, 28869
NCBI Taxonomy refs (TaxIDs): 1288825Reference(s) to other database(s): GTC:G78578OH, GlycomeDB:
37318
Show glycosyltransferases
NMR conditions: in D2O at 306 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2,3 aDGlcp 95.9 72.8 74.6 71.0 72.8 62.1
3,3,2 aLRhap 102.8 75.7 75.1 72.3 70.7 18.4
3,3 aLRhap 102.7 80.9 71.2 73.6 70.7 18.1
3,4 aDGlcp 98.7 72.7 74.1 71.2 73.2 61.8
3 aLRhap 102.4 72.2 80.5 76.1 70.4 19.3
2 Ac 175.4 24.1
bDGlcpN 103.0 56.8 83.0 69.8 77.4 62.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2,3 aDGlcp 5.18 3.72 3.83 3.50 4.04 3.79-3.87
3,3,2 aLRhap 5.12 4.43 3.95 3.36 3.79 1.30
3,3 aLRhap 5.05 4.11 3.88 3.49 3.79 1.31
3,4 aDGlcp 5.19 3.55 3.72 3.43 3.96 3.78-3.83
3 aLRhap 4.83 3.92 3.92 3.79 4.15 1.34
2 Ac - 2.11
bDGlcpN 4.80 3.86 3.49 3.54 3.48 3.76-3.91
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2,3 aDGlcp 95.9/5.18 72.8/3.72 74.6/3.83 71.0/3.50 72.8/4.04 62.1/3.79-3.87
3,3,2 aLRhap 102.8/5.12 75.7/4.43 75.1/3.95 72.3/3.36 70.7/3.79 18.4/1.30
3,3 aLRhap 102.7/5.05 80.9/4.11 71.2/3.88 73.6/3.49 70.7/3.79 18.1/1.31
3,4 aDGlcp 98.7/5.19 72.7/3.55 74.1/3.72 71.2/3.43 73.2/3.96 61.8/3.78-3.83
3 aLRhap 102.4/4.83 72.2/3.92 80.5/3.92 76.1/3.79 70.4/4.15 19.3/1.34
2 Ac 24.1/2.11
bDGlcpN 103.0/4.80 56.8/3.86 83.0/3.49 69.8/3.54 77.4/3.48 62.2/3.76-3.91
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2,3 | aDGlcp | 5.18 | 3.72 | 3.83 | 3.50 | 4.04 | 3.79
3.87 |
| 3,3,2 | aLRhap | 5.12 | 4.43 | 3.95 | 3.36 | 3.79 | 1.30 |
| 3,3 | aLRhap | 5.05 | 4.11 | 3.88 | 3.49 | 3.79 | 1.31 |
| 3,4 | aDGlcp | 5.19 | 3.55 | 3.72 | 3.43 | 3.96 | 3.78
3.83 |
| 3 | aLRhap | 4.83 | 3.92 | 3.92 | 3.79 | 4.15 | 1.34 |
| 2 | Ac |
| 2.11 | |
| | bDGlcpN | 4.80 | 3.86 | 3.49 | 3.54 | 3.48 | 3.76
3.91 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2,3 | aDGlcp | 95.9 | 72.8 | 74.6 | 71.0 | 72.8 | 62.1 |
| 3,3,2 | aLRhap | 102.8 | 75.7 | 75.1 | 72.3 | 70.7 | 18.4 |
| 3,3 | aLRhap | 102.7 | 80.9 | 71.2 | 73.6 | 70.7 | 18.1 |
| 3,4 | aDGlcp | 98.7 | 72.7 | 74.1 | 71.2 | 73.2 | 61.8 |
| 3 | aLRhap | 102.4 | 72.2 | 80.5 | 76.1 | 70.4 | 19.3 |
| 2 | Ac | 175.4 | 24.1 | |
| | bDGlcpN | 103.0 | 56.8 | 83.0 | 69.8 | 77.4 | 62.2 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
