Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: bacillary dysentery [ICD11:
1A02 
, ICD11:
XN7HG ];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
The structure was elucidated in this paperNCBI PubMed ID: 19376498Publication DOI: 10.1016/j.carres.2009.03.022Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
The O-specific polysaccharide (O-antigen) structure of a Shigella flexneri type 4a strain from the Dysentery Reference Laboratory (London, UK) was elucidated in 1978 and its characteristic feature was found to be α-D-glucosylation of GlcNAc at position 6, which defines O-factor IV. Our NMR spectroscopic studies of the O-specific polysaccharides of two other strains belonging to S. flexneri type 4a (G1668 from Adelaide, Australia, and 1359 from Moscow, Russia) confirmed the carbohydrate backbone structure but revealed in both strains an additional component, ethanolamine phosphate (EtnP), attached at position 3 of one of the rhamnose residues: [structure: see text]. Phosphorylation has not been hitherto reported in any S. flexneri O-antigen. Reinvestigation of the O-specific polysaccharide of S. flexneri type 4b showed that it is not phosphorylated and confirmed its structure established earlier.
O-antigen, Shigella flexneri, O-acetylation, Ethanolamine phosphate, bacterial polysaccharide structure
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.1589, chart 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_120354,IEDB_123890,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_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, alkaline degradation, mild acid degradation
Related record ID(s): 24173
NCBI Taxonomy refs (TaxIDs): 984898Reference(s) to other database(s): GTC:G14472EM
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2,3,0 xXEtN
3,3,2,3 P
3,3,2 aLRhap 102.7 79.0 76.6 72.7 70.7 18.2
3,3 aLRhap 102.2 80.3 71.4 73.7 70.5 18.0
3 aLRhap 102.7 72.0 78.4 73.0 70.4 17.9
2 Ac 175.7 23.8
6 aDGlcp 99.5 73.0 74.5 71.0 73.5 62.0
bDGlcpN 104.0 56.9 82.6 69.7 75.7 67.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2,3,0 xXEtN
3,3,2,3 P
3,3,2 aLRhap 5.06 4.33 4.26 3.37 3.72 1.25
3,3 aLRhap 5.19 4.07 3.90 3.52 3.76 1.31
3 aLRhap 4.89 3.86 3.80 3.56 4.02 1.25
2 Ac - 2.09
6 aDGlcp 4.98 3.56 3.76 3.42 3.71 3.76-3.86
bDGlcpN 4.74 3.89 3.68 3.68 3.67 3.80-3.97
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2,3,0 xXEtN
3,3,2,3 P
3,3,2 aLRhap 102.7/5.06 79.0/4.33 76.6/4.26 72.7/3.37 70.7/3.72 18.2/1.25
3,3 aLRhap 102.2/5.19 80.3/4.07 71.4/3.90 73.7/3.52 70.5/3.76 18.0/1.31
3 aLRhap 102.7/4.89 72.0/3.86 78.4/3.80 73.0/3.56 70.4/4.02 17.9/1.25
2 Ac 23.8/2.09
6 aDGlcp 99.5/4.98 73.0/3.56 74.5/3.76 71.0/3.42 73.5/3.71 62.0/3.76-3.86
bDGlcpN 104.0/4.74 56.9/3.89 82.6/3.68 69.7/3.68 75.7/3.67 67.0/3.80-3.97
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2,3,0 | xXEtN | |
| 3,3,2,3 | P | |
| 3,3,2 | aLRhap | 5.06 | 4.33 | 4.26 | 3.37 | 3.72 | 1.25 |
| 3,3 | aLRhap | 5.19 | 4.07 | 3.90 | 3.52 | 3.76 | 1.31 |
| 3 | aLRhap | 4.89 | 3.86 | 3.80 | 3.56 | 4.02 | 1.25 |
| 2 | Ac |
| 2.09 | |
| 6 | aDGlcp | 4.98 | 3.56 | 3.76 | 3.42 | 3.71 | 3.76
3.86 |
| | bDGlcpN | 4.74 | 3.89 | 3.68 | 3.68 | 3.67 | 3.80
3.97 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2,3,0 | xXEtN | |
| 3,3,2,3 | P | |
| 3,3,2 | aLRhap | 102.7 | 79.0 | 76.6 | 72.7 | 70.7 | 18.2 |
| 3,3 | aLRhap | 102.2 | 80.3 | 71.4 | 73.7 | 70.5 | 18.0 |
| 3 | aLRhap | 102.7 | 72.0 | 78.4 | 73.0 | 70.4 | 17.9 |
| 2 | Ac | 175.7 | 23.8 | |
| 6 | aDGlcp | 99.5 | 73.0 | 74.5 | 71.0 | 73.5 | 62.0 |
| | bDGlcpN | 104.0 | 56.9 | 82.6 | 69.7 | 75.7 | 67.0 |
|
There is only one chemically distinct structure:
Found 
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