Uronosyl phosphonate-based sialidase inhibitor synthesis and conformational analysis

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Bhatt, Beenu
Thomson, Robin J
von Itzstein, Mark
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2012
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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 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.

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Bioorganic & Medicinal Chemistry Letters

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22

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24

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Medicinal and biomolecular chemistry

Biologically active molecules

Organic chemistry

Organic chemical synthesis

Pharmacology and pharmaceutical sciences

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