Peptide ligation from alkoxyamine based radical addition

Thomas Trimaille; Laurent Autissier; Mamy Daniel Rakotonirina; Yohann Guillaneuf; Claude Villard; Denis Bertin; Didier Gigmes; Kamel Mabrouk

doi:10.1039/C3CC49389J

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Peptide ligation from alkoxyamine based radical addition†

Thomas Trimaille,*^a Laurent Autissier,^a Mamy Daniel Rakotonirina,^a Yohann Guillaneuf,^a Claude Villard,^b Denis Bertin,^a Didier Gigmes^a and Kamel Mabrouk*^a

Author affiliations

* Corresponding authors

^a Aix-Marseille Université, CNRS, UMR 7273, 13397 Marseille Cedex 20, France
E-mail: thomas.trimaille@univ-amu.fr, kamel.mabrouk@univ-amu.fr
Fax: +33 4 9128 8758
Tel: +33 4 9128 8083

^b Aix-Marseille Université, INSERM, UMR 911 CRO2, 13385 Marseille, France

Abstract

Intermolecular radical 1,2-addition (IRA) of N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl (SG1) based alkoxyamines onto activated olefins is used as a tool for peptide ligation. This strategy relies on simple peptide pre-derivatization to obtain (i) a SG1 nitroxide functionalized resin peptide at its N-terminus (SG1-peptide alkoxyamine), (ii) a vinyl functionalized peptide (either at its C-terminus or N-terminus), and does not require any coupling agents.

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Supplementary files

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Article information

DOI: https://doi.org/10.1039/C3CC49389J
Article type: Communication
Submitted: 10 Dec 2013
Accepted: 09 Jan 2014
First published: 17 Jan 2014
This article is Open Access

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Chem. Commun., 2014,50, 2744-2747

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Peptide ligation from alkoxyamine based radical addition

T. Trimaille, L. Autissier, M. D. Rakotonirina, Y. Guillaneuf, C. Villard, D. Bertin, D. Gigmes and K. Mabrouk, Chem. Commun., 2014, 50, 2744 DOI: 10.1039/C3CC49389J

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Chemical Communications

Peptide ligation from alkoxyamine based radical addition†

Abstract

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Peptide ligation from alkoxyamine based radical addition

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