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Uronosyl phosphonate-based sialidase inhibitor synthesis and conformational analysis

Bioorganic & medicinal chemistry letters | 6 Nov 2012

B Bhatt, RJ Thomson and M von Itzstein
Abstract
With a view to development of novel sialidase inhibitors, mimetics of the natural inhibitor Neu5Ac2en have been prepared in which a phosphonate group replaces the sialic acid glycerol side chain. Different hex-4-en derivatives adopt half-chair conformations that place the glycosyl phosphonate in an equatorial position. For the α-L-threo-hex-4-en derivative this conformation is equivalent to that of Neu5Ac2en, and opposite to that seen for alkyl O-glycosides with the same overall stereochemistry.
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Concepts
Calculus, Vector space, Tertiary structure, Cyclohexane conformation, Conformation, Derivative, Stereochemistry, Conformational isomerism
MeSH headings
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