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Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain†
Nicolas Ardes-Guisot,Dominic S. Alonzi,Gabriele Reinkensmeier,Terry D. Butters,Caroline Norez,Frédéric Becq,Yousuke Shimada,Shinpei Nakagawa,Atsushi Kato,Yves Blériot,Matthieu Sollogoub,Boris Vauzeilles
Organic & Biomolecular Chemistry Pub Date : 03/21/2011 00:00:00 , DOI:10.1039/C1OB05119A
Abstract

A series of neoglycoconjugates derived from deoxynojirimycin has been prepared by click connection with functionalised adamantanes. They have been assayed as glycosidase inhibitors, as inhibitors of the glycoenzymes relevant to the treatment of Gaucher disease, as well as correctors of the defective ion-transport protein involved in cystic fibrosis. We have demonstrated that it is possible to selectively either strongly inhibit ER-α-glucosidases and ceramide glucosyltransferase or restore the activity of CFTR in CF-KM4 cells by varying the length of the alkyl chain linking DNJ and adamantane.

Graphical abstract: Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain
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