Inverse Peptide Synthesis via Activated [alpha]-Aminoesters

A mild, practical, and simple procedure for peptide-bond formation is reported. Instead of activation of the carboxylic acid functionality, the reaction involves an unprecedented use of activated [alpha]-aminoesters. The method provides a straightforward entry to dipeptides and was effective when a...

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Veröffentlicht in:	Angewandte Chemie International Edition 2014-05, Vol.53 (21), p.5389-5393
Hauptverfasser:	Suppo, Jean-Simon, Subra, Gilles, Berges, Matthieu, MarciadeFigueiredo, Renata, Campagne, Jean-Marc
Format:	Artikel
Sprache:	eng
Schlagworte:	Activated Carboxylic acids Chemical industry Cysteine Formations Inverse Iterative methods Peptides Residues Synthesis
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creator	Suppo, Jean-Simon Subra, Gilles Berges, Matthieu MarciadeFigueiredo, Renata Campagne, Jean-Marc
description	A mild, practical, and simple procedure for peptide-bond formation is reported. Instead of activation of the carboxylic acid functionality, the reaction involves an unprecedented use of activated [alpha]-aminoesters. The method provides a straightforward entry to dipeptides and was effective when a sensitive cysteine residue was used, as no epimerization was detected in this case. The applicability of this method to iterative peptide synthesis was illustrated by the synthesis of a model tetrapeptide in the challenging reverse N[arrow right]C direction. [PUBLICATION ABSTRACT]
doi_str_mv	10.1002/anie.201402147
format	Article
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source	Wiley Online Library Journals Frontfile Complete
subjects	Activated Carboxylic acids Chemical industry Cysteine Formations Inverse Iterative methods Peptides Residues Synthesis
title	Inverse Peptide Synthesis via Activated [alpha]-Aminoesters
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