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  • A drug targeting motif for glycosidase inhibitors: an iminosugar-boronate shows unexpectedly selective b-galactosidase inhibition

    Author(s)
    Johnson, LL
    Houston, TA
    Griffith University Author(s)
    Houston, Todd A.
    Year published
    2002
    Metadata
    Show full item record
    Abstract
    Boronic acids were tethered to iminosugars in compounds such as 8 and 13 in order to increase their affinity for cell surfaces where glycoprotein processing enzymes are operative. Surprisingly, this modification diminished a-mannosidase inhibition while increasing ߭galactosidase inhibitory activity (8: Ki=2.0ױ0-4 M versus E. coli ߭galactosidase). The presence of a boronate in 8 and 13 has a profound impact on the specificity of this inhibition.Boronic acids were tethered to iminosugars in compounds such as 8 and 13 in order to increase their affinity for cell surfaces where glycoprotein processing enzymes are operative. Surprisingly, this modification diminished a-mannosidase inhibition while increasing ߭galactosidase inhibitory activity (8: Ki=2.0ױ0-4 M versus E. coli ߭galactosidase). The presence of a boronate in 8 and 13 has a profound impact on the specificity of this inhibition.
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    Journal Title
    Tetrahedron Letters
    Volume
    43
    DOI
    https://doi.org/10.1016/S0040-4039(02)02196-2
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/7014
    Collection
    • Journal articles

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