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

Authors: Jobin, SteveMéjean, AlexiaGalindo, Sindy-MarcelaLiang, XinxiaVézina-Dawod, SimonBiron, Éric
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.
Document Type: Article de recherche
Issue Date: 14 November 2016
Open Access Date: 14 November 2017
Document version: AM
Permalink: http://hdl.handle.net/20.500.11794/12708
This document was published in: Organic and biomolecular chemistry, Vol. 14 (47), 11230-11237 (2016)
http://dx.doi.org/10.1039/C6OB02342H
Royal Society of Chemistry
Alternative version: 10.1039/C6OB02342H
27841889
Collection:Articles publiés dans des revues avec comité de lecture

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