Issue 20, 2018

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 the resistance towards proteolysis and improving the biological activity, only very rare examples of the incorporation of two or more consecutive aza-amino acids have been reported. In this work, we demonstrate that this fact is probably due to the unsuspected difficulty in synthesizing 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
20 Jul 2018
Accepted
10 Sep 2018
First published
10 Sep 2018

New J. Chem., 2018,42, 17062-17072

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, 42, 17062 DOI: 10.1039/C8NJ03635G

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