Construction of giant glycosidase inhibitors from iminosugar-substituted fullerene macromonomers

J Mater Chem B. 2017 Aug 28;5(32):6546-6556. doi: 10.1039/c7tb01052d. Epub 2017 May 25.

Abstract

An ultra-fast synthetic procedure based on grafting of twelve fullerene macromonomers onto a fullerene hexa-adduct core was used for the preparation of a giant molecule with 120 peripheral iminosugar residues. The inhibition profile of this giant iminosugar ball was evaluated against various glycosidases. In the particular case of the Jack bean α-mannosidase, a dramatic enhancement of the glycosidase inhibitory effect was observed for the giant molecule with 120 peripheral subunits as compared to that of the corresponding mono- and dodecavalent model compounds.