Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Shigella dysenteriae [ICD11:
XN285 
]
The structure was elucidated in this paperNCBI PubMed ID: 18695724Publication DOI: 10.1134/S1068162008040109Journal NLM ID: 9420101Publisher: Springer Science and Business Media
Correspondence: perepel
ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia,TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, China
The earlier established structures of the acidic O-specific polysaccharides from two typical strains of the Shigella dysenteriae bacterium were revised using modern NMR spectroscopy techniques. In particular, the configurations of the glycosidic linkages of GlcNAc (S. dysenteriae type 4) and mannose (S. dysenteriae type 5) residues were corrected. In addition, the location of the sites of non-stoichiometric O-acetylation in S. dysenteriae type 4 was determined: the lateral fucose residue was shown to be occasionally O-acetylated; also, theposition of the O-acetyl group present at the stoichiometric quantity in S. dysenteriae type 5 was corrected. The revised structures of the polysaccharides studied are shown below. The known identity of theO-specific polysaccharide structures of S. dysenteriae type 5 and Escherichia coli O58 was confirmed by 13C NMR spectroscopy and, hence, the structure of the E. coli O58 polysaccharide should be revised in the same manner.
structure, O-antigen, NMR spectroscopy, O-specific polysaccharide, O-Specific polysaccharide structure, Shigella dysenteriae
Structure type: suggested polymer biological repeating unit
Location inside paper: p.462, DPS, Table 2
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_136045,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151531,IEDB_152214,IEDB_174333,SB_74,SB_85,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, GLC, mild acid hydrolysis, alkaline degradation, Smith degradation, NMR-1D
Comments, role: O-deacetylated polysaccharide (DPS)
Related record ID(s): 21481, 22716, 23211, 23213, 23214, 23215, 23216, 26212
NCBI Taxonomy refs (TaxIDs): 1633494Reference(s) to other database(s): GTC:G69278UM, GlycomeDB:
34667
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,4,2 Ac 175.7-176.2 23.5-23.7
3,3,4,3 aLFucp 99.7 69.2 70.7 73.3 68.0 16.9
3,3,4 aDGlcpN 99.6 55.3 73.3 79.3 73.3 60.8
3,3 aDGlcpA 102.0 73.3 74.6 79.3 73.7 175.7
3 aLFucp 101.6 68.7 74.6 73.7 68.4 16.5
2 Ac 175.7-176.2 23.5-23.7
bDGlcpN 101.5 57.0 81.9 70.9 77.6 63.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,4,2 Ac - 2.02-2.4
3,3,4,3 aLFucp 5.11 3.68 3.95 3.79 4.72 1.25
3,3,4 aDGlcpN 5.17 4.13 3.91 3.87 3.72 3.72-3.83
3,3 aDGlcpA 5.17 3.57 3.73 3.73 4.18 -
3 aLFucp 4.97 3.88 3.89 3.91 4.31 1.14
2 Ac - 2.02-2.4
bDGlcpN 4.55 3.80 3.63 3.31 3.44 3.59-3.96
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,4,2 Ac 23.5-23.7/2.02-2.4
3,3,4,3 aLFucp 99.7/5.11 69.2/3.68 70.7/3.95 73.3/3.79 68.0/4.72 16.9/1.25
3,3,4 aDGlcpN 99.6/5.17 55.3/4.13 73.3/3.91 79.3/3.87 73.3/3.72 60.8/3.72-3.83
3,3 aDGlcpA 102.0/5.17 73.3/3.57 74.6/3.73 79.3/3.73 73.7/4.18
3 aLFucp 101.6/4.97 68.7/3.88 74.6/3.89 73.7/3.91 68.4/4.31 16.5/1.14
2 Ac 23.5-23.7/2.02-2.4
bDGlcpN 101.5/4.55 57.0/3.80 81.9/3.63 70.9/3.31 77.6/3.44 63.2/3.59-3.96
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,4,2 | Ac |
| 2.02
2.4 | |
| 3,3,4,3 | aLFucp | 5.11 | 3.68 | 3.95 | 3.79 | 4.72 | 1.25 |
| 3,3,4 | aDGlcpN | 5.17 | 4.13 | 3.91 | 3.87 | 3.72 | 3.72
3.83 |
| 3,3 | aDGlcpA | 5.17 | 3.57 | 3.73 | 3.73 | 4.18 |
|
| 3 | aLFucp | 4.97 | 3.88 | 3.89 | 3.91 | 4.31 | 1.14 |
| 2 | Ac |
| 2.02
2.4 | |
| | bDGlcpN | 4.55 | 3.80 | 3.63 | 3.31 | 3.44 | 3.59
3.96 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,4,2 | Ac | 175.7
176.2 | 23.5
23.7 | |
| 3,3,4,3 | aLFucp | 99.7 | 69.2 | 70.7 | 73.3 | 68.0 | 16.9 |
| 3,3,4 | aDGlcpN | 99.6 | 55.3 | 73.3 | 79.3 | 73.3 | 60.8 |
| 3,3 | aDGlcpA | 102.0 | 73.3 | 74.6 | 79.3 | 73.7 | 175.7 |
| 3 | aLFucp | 101.6 | 68.7 | 74.6 | 73.7 | 68.4 | 16.5 |
| 2 | Ac | 175.7
176.2 | 23.5
23.7 | |
| | bDGlcpN | 101.5 | 57.0 | 81.9 | 70.9 | 77.6 | 63.2 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
