|Title||1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines|
|Publication Type||Journal Article|
|Year of Publication||2010|
|Authors||Froehlich, RFG, Furneaux, RH, Mahuran, DJ, Rigat, BA, Stuetz, AE, Tropak, MB, Wicki, J, Withers, SG, Wrodnigg, TM|
|Date Published||JUL 2|
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.