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  • An efficient approach to N-acetyl-D-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors

    Author(s)
    Mann, MC
    Thomson, RJ
    von Itzstein, M
    Griffith University Author(s)
    von Itzstein, Mark
    Thomson, Robin J.
    Year published
    2004
    Metadata
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    Abstract
    A novel approach to the synthesis of ߭glycosides of N-acetyl-D-glucosaminuronic acid, in six steps and good overall yield from N-acetyl-D-glucosamine, has been developed. The key synthetic step was the Lewis acid mediated O-glycosidation of methyl 1,3,4-tri-O-pivaloyl-N-acetyl-D-glucosaminuronate (11). Elaboration of glucosaminuronides 15 and 18 provided novel sialylmimetics 21 and 22, which showed inhibition of Vibrio cholerae sialidase.A novel approach to the synthesis of ߭glycosides of N-acetyl-D-glucosaminuronic acid, in six steps and good overall yield from N-acetyl-D-glucosamine, has been developed. The key synthetic step was the Lewis acid mediated O-glycosidation of methyl 1,3,4-tri-O-pivaloyl-N-acetyl-D-glucosaminuronate (11). Elaboration of glucosaminuronides 15 and 18 provided novel sialylmimetics 21 and 22, which showed inhibition of Vibrio cholerae sialidase.
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    Journal Title
    Biorganic & Medicinal Chemistry Letters
    Volume
    14
    Publisher URI
    http://www.elsevier.com/wps/find/journaldescription.cws_home/972/description#description
    DOI
    https://doi.org/10.1016/j.bmcl.2004.08.064
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/5049
    Collection
    • Journal articles

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