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  • Title: Iminoalditol-amino acid hybrids: synthesis and evaluation as glycosidase inhibitors.
    Author: Steiner AJ, Stütz AE, Tarling CA, Withers SG, Wrodnigg TM.
    Journal: Carbohydr Res; 2007 Sep 03; 342(12-13):1850-8. PubMed ID: 17442281.
    Abstract:
    Cyclization by double reductive amination of D-xylo-hexos-5-ulose with the terminal amino group of alpha-N-Boc-lysine methyl ester gave a 4:1-mixture of (1'R)-N-methoxycarbonyl-(1-N-Boc-amino)pentyl-1-deoxynojirimycin and the corresponding L-ido epimer whereas D-lyxo-hexos-5-ulose furnished the desired N-alkylated 1-deoxymannojirimycin derivative without any observable epimer formation at C-5. By subsequent modification of the lysine moiety, additional chain-extended derivatives as well as fluorescent compounds were obtained. All fluorescent iminoalditol-amino acid hybrids prepared in this study exhibited glycosidase inhibitory activities better than or comparable to the parent compounds'.
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