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Issue 47, 2016
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Toward solid-phase peptide fragment ligation by a traceless-Ugi multicomponent reaction approach

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Abstract

A new methodology to couple peptide fragments on solid support using a traceless isocyanide-based multicomponent reaction is described. The approach uses a microwave-assisted on-resin Ugi four-component reaction to attach a carboxyl free peptide to a supported peptide bearing a free N-terminal amine via the formation of an N-protected amide bond at the ligation site. Afterward, the generated backbone amide protecting group can be efficiently removed by microwave-assisted acidolysis with trifluoroacetic acid to afford a fully deprotected peptide. This straightforward Ugi reaction/deprotection approach was applied to condense various fragment lengths and provided a variety of oligopeptides.

Graphical abstract: Toward solid-phase peptide fragment ligation by a traceless-Ugi multicomponent reaction approach

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Article information


Submitted
27 Oct 2016
Accepted
09 Nov 2016
First published
14 Nov 2016

Org. Biomol. Chem., 2016,14, 11230-11237
Article type
Paper

Toward solid-phase peptide fragment ligation by a traceless-Ugi multicomponent reaction approach

S. Jobin, A. Méjean, S. Galindo, X. Liang, S. Vézina-Dawod and E. Biron, Org. Biomol. Chem., 2016, 14, 11230
DOI: 10.1039/C6OB02342H

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