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Issue 3, 2016
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A metal-free synthetic approach to peptide-based iminosugar clusters as novel multivalent glycosidase inhibitors

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Abstract

Multivalent bioconjugates represent emerging tools for enzyme inhibition. In particular, iminosugar clusters have recently shown promising results for the inhibition of glycosidases. However, most of them are prepared by copper-mediated click reactions. We report herein a metal-free approach based on oxime ligation for preparing iminosugar clusters using cyclic and linear tetra-aldehyde peptide scaffolds and oxyamine iminosugars (40–70% yield). Glycosidase inhibition assays revealed the superiority of the clusters made of the linear scaffold, displaying up to a 77-fold increase of relative potency per iminosugar. Thus, this metal-free approach provides a rapid access to structurally-diverse iminosugar clusters for establishing structure–activity relationships in the context of multivalent glycosidase inhibition.

Graphical abstract: A metal-free synthetic approach to peptide-based iminosugar clusters as novel multivalent glycosidase inhibitors

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Supplementary files

Article information


Submitted
02 Oct 2015
Accepted
16 Dec 2015
First published
04 Jan 2016

RSC Adv., 2016,6, 2210-2216
Article type
Paper

A metal-free synthetic approach to peptide-based iminosugar clusters as novel multivalent glycosidase inhibitors

R. Zelli, E. Bartolami, J. Longevial, Y. Bessin, P. Dumy, A. Marra and S. Ulrich, RSC Adv., 2016, 6, 2210
DOI: 10.1039/C5RA20420H

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