Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-D-mannitol: Syntheses and glycosidase-inhibitory activities of 1,2,5-trideoxy-2-fluoro-1,5-imino-D-glucitol and of 1,2,5-trideoxy-1-fluoro-2,5-imino-D-mannitol

Søren Møller Andersen, Michael Ebner, Christian W. Ekhart, Günther Gradnig, Günther Legler, Inge Lundt, A.E. Stütz, S.G. Withers, T. Wrodnigg

    Research output: Contribution to journalJournal articleResearch


    1,2,5-trideoxy-2-fluoro-1,5-imino-D-glucitol, the 2-deoxyfluoro derivative of 1-deoxynojirimycin, as well as 1,2,5-trideoxy-1-fluoro-2,5-imino-D-mannitol and 2,5-dideoxy-2,5-imino-1-O-methyl-D-mannitol, two new analogues of the natural product and powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, were synthesised featuring glucose isomerase-catalysed aldose-ketose interconvertion reactions as the key steps of the syntheses.Results of inhibition studies conducted with these compounds and previously obtained deoxyfluoro derivatives of 1-deoxynojirimycin, employing glucosidases from various sources, showed that the replacement of a hydroxyl function by fluorine caused an impairment of the inhibitory potency. This effect was smallest for the hydroxyl group at C-6 and up to four orders of magnitude larger for replacements at C-2 and C-3.
    Original languageEnglish
    JournalCarbohydrate Research 301
    Pages (from-to)155-166
    Publication statusPublished - 1997

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