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Convergent Synthesis and Conformational Analysis of the Hexasaccharide Repeating Unit of the O ‐Antigen of Shigella flexneri Serotype 1d
Author(s) -
Dhara Debashis,
Kar Rajiv Kumar,
Bhunia Anirban,
Misra Anup Kumar
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402392
Subject(s) - shigella flexneri , chemistry , glycosylation , glycosidic bond , stereochemistry , glycosyl , oligosaccharide , escherichia coli , biochemistry , gene , enzyme
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.