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1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines

Title1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines
Publication TypeJournal Article
Year of Publication2010
AuthorsFroehlich, RFG, Furneaux, RH, Mahuran, DJ, Rigat, BA, Stuetz, AE, Tropak, MB, Wicki, J, Withers, SG, Wrodnigg, TM
JournalCARBOHYDRATE RESEARCH
Volume345
Pagination1371-1376
Date PublishedJUL 2
ISSN0008-6215
Abstract

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.

DOI10.1016/j.carres.2010.04.015