Journal
CARBOHYDRATE RESEARCH
Volume 345, Issue 10, Pages 1371-1376Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.04.015
Keywords
Iminoalditol; N-AlKylation; Glucosidase inhibitor; Molecular chaperone; Gaucher's disease
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Cyclization by double reductive amination of D-xylo-hexos-5-ulose with methyl 6-aminohexanoate gave (methoxycarbonyl)pentyl-1-deoxynojirimycin. Reaction of the terminal carboxylic acid with N-dansyl-1,6-diaminohexane provided the corresponding chain-extended fluorescent derivative. By reaction with bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Both compounds are strong inhibitors of D-glucosidases and could also be shown to distinctly improve, at sub-inhibitory concentrations, the activity of beta-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome. (C) 2010 Elsevier Ltd. All rights reserved.
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