Toward solid-phase peptide fragment ligation by a traceless-Ugi multicomponent reaction approach
Authors: | Jobin, Steve; Méjean, Alexia; Galindo, Sindy-Marcela; Liang, Xinxia; Vézina-Dawod, Simon; Biron, 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) https://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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Jobin_OBC_2016_Article.docx | 5.73 MB | Microsoft Word XML | View/Open | |
2016_Org&Biomol.Chem. 14_11230-11237.pdf | 1.15 MB | Adobe PDF | ![]() View/Open |
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