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Bioorg Med Chem Lett. 2012 Dec 15;22(24):7623-6. doi: 10.1016/j.bmcl.2012.10.015. Epub 2012 Oct 10.

Uronosyl phosphonate-based sialidase inhibitor synthesis and conformational analysis.

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  • 1Institute for Glycomics, Griffith University, Gold Coast Campus, Queensland 4222, Australia.

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.

Copyright © 2012 Elsevier Ltd. All rights reserved.

PMID:
23122861
[PubMed - indexed for MEDLINE]
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