1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines
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- 作者：Richard F.G. Frö ; hlich ; Richard H. Furneaux ; Don J. Mahuran ; Brigitte A. Rigat ; Arnold E. Stü ; tz ; Michael B. Tropak ; Jacqueline Wicki ; Stephen G. Withers ; Tanja M. Wrodnigg
- 关键词：Iminoalditol ; N-Alkylation ; Glucosidase inhibitor ; Molecular chaperone ; Gaucher’ ; s disease
- 刊名：Carbohydrate Research
- 出版年：2010
- 出版时间：2 July 2010
- 年：2010
- 卷：345
- 期：10
- 页码：1371-1376
- 全文大小：479 K
文摘
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 β-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome.