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 paperPublication DOI: 10.1002/ejoc.201402392Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: anirbanbhunia
gmail.coma (Anirban Bhuni); akmisra69
gmail.com (Anup Kumar Misra)
Institutions: Bose Institute, Division of Molecular Medicine, 1/12, C.I.T. Scheme VII-M, Kolkata 700054, India
A hexasaccharide repeating unit of the O-antigen of the cell wall of Shigella flexneri type 1d has been synthesized using a stereoselective [3+3] block glycosylation approach. Recently developed glycosylation conditions were used in the synthesis. A thioglycoside was used as an orthogonal glycosyl donor during the synthesis. The synthesized hexasaccharide was subjected to detailed NMR spectroscopic and molecular modeling studies to determine its conformational behavior in water. The NOE-based two-dimensional NOSEY experiment and all-atom explicit molecular dynamics (MD) simulation studies suggest that the oligosaccharide is not very flexible, that it remains rigid with respect to the glycosidic linkages between the sugar moieties.
carbohydrates, Oligosaccharides, molecular dynamics, conformation analysis, glycosylation, Synthetic methods
Structure type: oligomer ; 1049.4 [M+Na]+
C
40H
70N
2O
28Location inside paper: p.4578, fig.1, compound 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_120354,IEDB_125613,IEDB_133754,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_158539,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, chemical synthesis, chemical methods, MD simulations, glycosylation
Synthetic data: chemical
3D data: molecular modeling
NCBI Taxonomy refs (TaxIDs): 623
Show glycosyltransferases
1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
Found 
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