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Towards a general synthesis of di-aza-amino acids containing peptides

Abstract

While the incorporation of one aza-amino acid in peptides has been proved to be beneficial for inducing a structure constraint, increasing resistance towards proteolysis and improving biological activity, only very rare examples of the incorporation of two or more consecutive aza-amino acids have been reported. In this work, we demonstrated that this fact is probably due to the unsuspected difficulty to synthesize such peptide analogues, as illustrated by the synthesis of tripeptide derivatives containing two consecutive aza-amino acids. Herein, we report some general guidelines regarding the activation and the coupling of alkyl-hydrazides either mutually or with a natural amino acid, taking into account their nucleophilicity and the nature of their side chains.

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Publication details

The article was received on 20 Jul 2018, accepted on 10 Sep 2018 and first published on 10 Sep 2018


Article type: Paper
DOI: 10.1039/C8NJ03635G
Citation: New J. Chem., 2018, Accepted Manuscript
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    Towards a general synthesis of di-aza-amino acids containing peptides

    F. Bizet, N. Tonali, J. Soulier, A. OLIVA, J. Kaffy, B. Crousse and S. Ongeri, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ03635G

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