Jump to main content
Jump to site search

Issue 20, 2018
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

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., 2018,42, 17062-17072
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements