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  • Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid

    Author(s)
    Pearson, AG
    Kiefel, MJ
    Ferro, V
    von Itzstein, M
    Griffith University Author(s)
    von Itzstein, Mark
    Kiefel, Milton
    Pearson, Andrew G.
    Year published
    2005
    Metadata
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    Abstract
    This work describes our preliminary efforts towards the development of aryl glucuronides as potential probes for heparanase. During the course of these initial investigations, attempted glycosidation of methyl 2,3,4-tri-O-acetyl-a-d-glucopyranosyluronate trichloroacetimidate with 4-hydroxycinnamic acid gave a complex mixture of four different components. These were identified as the 1-cinnamyl glucuronate ester 13, the cinnamyl linked disaccharide 14, the glucuronate trichloroacetamide 15, and the glucuronyl a-fluoride 16. This paper rationalises the formation of each of these products, and reports our efforts in trying to ...
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    This work describes our preliminary efforts towards the development of aryl glucuronides as potential probes for heparanase. During the course of these initial investigations, attempted glycosidation of methyl 2,3,4-tri-O-acetyl-a-d-glucopyranosyluronate trichloroacetimidate with 4-hydroxycinnamic acid gave a complex mixture of four different components. These were identified as the 1-cinnamyl glucuronate ester 13, the cinnamyl linked disaccharide 14, the glucuronate trichloroacetamide 15, and the glucuronyl a-fluoride 16. This paper rationalises the formation of each of these products, and reports our efforts in trying to optimise the formation of the a-fluoride 16.
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    Journal Title
    Carbohydrate Research
    Volume
    340
    Issue
    13
    Publisher URI
    http://www.elsevier.com/wps/find/journaldescription.cws_home/424829/description#description
    DOI
    https://doi.org/10.1016/j.carres.2005.06.029
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Biochemistry and cell biology
    Publication URI
    http://hdl.handle.net/10072/4188
    Collection
    • Journal articles

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