Iminoalditol-amino acid hybrids: synthesis and evaluation as glycosidase inhibitors

Cyclization by double reductive amination of d-xylo-hexos-5-ulose with the terminal amino group of α-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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