Issue 14, 2019
From the journal:

Organic Chemistry Frontiers

Diversity-oriented submonomer synthesis of azapeptides mediated by the Mitsunobu reaction†

Chuan Dai,a   Jun Ma,a   Min Li,a   Wen Wu,a   Xuefeng Xia*a  and  Jinqiang Zhang ORCID logo *a  

* Corresponding authors

a Innovative Drug Research Centre (IDRC), Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China
E-mail: j.zhang1983@cqu.edu.cn

Abstract

Azapeptides represent a class of peptidomimetics and exhibit important utilizations in drug discovery. Diversity-oriented synthesis of azapeptides is challenging due to the complexity of hydrazine chemistry and peptide coupling. Here we report an improved procedure of submonomer azapeptide synthesis by selective alkylation of semicarbazone using various alcohols mediated by the Mitsunobu reaction. The effectiveness of this new strategy was further proved by synthesizing a series of azapeptidomimetics of angiotensin 1–7.

Graphical abstract: Diversity-oriented submonomer synthesis of azapeptides mediated by the Mitsunobu reaction

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Article information

DOI
https://doi.org/10.1039/C9QO00296K
Article type
Research Article
Submitted
28 Feb 2019
Accepted
29 May 2019
First published
31 May 2019

Org. Chem. Front., 2019,6, 2529-2533

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Diversity-oriented submonomer synthesis of azapeptides mediated by the Mitsunobu reaction

C. Dai, J. Ma, M. Li, W. Wu, X. Xia and J. Zhang, Org. Chem. Front., 2019, 6, 2529 DOI: 10.1039/C9QO00296K

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