Uronosyl phosphonate-based sialidase inhibitor synthesis and conformational analysis
Author(s)
Bhatt, Beenu
Thomson, Robin J
von Itzstein, Mark
Year published
2012
Metadata
Show full item recordAbstract
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 a-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.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 a-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.
View less >
View less >
Journal Title
Bioorganic & Medicinal Chemistry Letters
Volume
22
Issue
24
Subject
Medicinal and biomolecular chemistry
Biologically active molecules
Organic chemistry
Organic chemical synthesis
Pharmacology and pharmaceutical sciences