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Construction of giant glycosidase inhibitors from iminosugar-substituted fullerene macromonomers

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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.

Graphical abstract: Construction of giant glycosidase inhibitors from iminosugar-substituted fullerene macromonomers

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Publication details

The article was received on 17 Apr 2017, accepted on 10 May 2017 and first published on 10 May 2017


Article type: Paper
DOI: 10.1039/C7TB01052D
Citation: J. Mater. Chem. B, 2017, Advance Article
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    Construction of giant glycosidase inhibitors from iminosugar-substituted fullerene macromonomers

    T. M. N. Trinh, M. Holler, J. P. Schneider, M. I. García-Moreno, J. M. García Fernández, A. Bodlenner, P. Compain, C. Ortiz Mellet and J. Nierengarten, J. Mater. Chem. B, 2017, Advance Article , DOI: 10.1039/C7TB01052D

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