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  • Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase

    Author(s)
    Bhatt, Beenu
    Boehm, Raphael
    Kerry, Philip S
    Dyason, Jeffrey C
    Russell, Rupert JM
    Thomson, Robin J
    von Itzstein, Mark
    Griffith University Author(s)
    von Itzstein, Mark
    Thomson, Robin J.
    Dyason, Jeffrey C.
    Bhatt, Beenu
    Bohm, Raphael
    Year published
    2012
    Metadata
    Show full item record
    Abstract
    A series of C3 O-functionalized 2-acetamido-2-deoxy-?4-߭D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the in?uenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits in?uenza virus sialidase at a sub-占level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.A series of C3 O-functionalized 2-acetamido-2-deoxy-?4-߭D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the in?uenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits in?uenza virus sialidase at a sub-占level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.
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    Journal Title
    Journal of Medicinal Chemistry
    Volume
    55
    Issue
    20
    DOI
    https://doi.org/10.1021/jm301145k
    Copyright Statement
    Self-archiving of the author-manuscript version is not yet supported by this journal. Please refer to the journal link for access to the definitive, published version or contact the authors for more information.
    Subject
    Medicinal and biomolecular chemistry
    Biomolecular modelling and design
    Organic chemistry
    Organic chemical synthesis
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/48670
    Collection
    • Journal articles

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