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  • Uronosyl phosphonate-based sialidase inhibitor synthesis and conformational analysis

    Author(s)
    Bhatt, Beenu
    Thomson, Robin J
    von Itzstein, Mark
    Griffith University Author(s)
    von Itzstein, Mark
    Thomson, Robin J.
    Year published
    2012
    Metadata
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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.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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    Journal Title
    Bioorganic & Medicinal Chemistry Letters
    Volume
    22
    Issue
    24
    DOI
    https://doi.org/10.1016/j.bmcl.2012.10.015
    Subject
    Medicinal and biomolecular chemistry
    Biologically active molecules
    Organic chemistry
    Organic chemical synthesis
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/48728
    Collection
    • Journal articles

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