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Article Dans Une Revue RSC Advances Année : 2016

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

Résumé

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.

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Chimie
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hal-03547008 , version 1 (28-01-2022)

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Renaud Zelli, Eline Bartolami, Jean-François Longevial, Yannick Bessin, Pascal Dumy, et al.. A metal-free synthetic approach to peptide-based iminosugar clusters as novel multivalent glycosidase inhibitors. RSC Advances, 2016, 6 (3), pp.2210-2216. ⟨10.1039/c5ra20420h⟩. ⟨hal-03547008⟩
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