Issue 24, 2022

Ugi and Passerini reactions enable the incorporation of ΔAA into N-alkylated peptides and depsipeptides

Abstract

This work renders operational simplicity under mild conditions to synthesize some N-alkylated peptides and depsipeptides containing olefins. A sequential one-pot protocol merging a multicomponent reaction with oxidative elimination of phenylselenoxide allows the formation of α,β and β,γ olefin containing peptides and depsipeptides. Consequently, the regioselective construction of α,β-dehydrobutyrine and α,β-dehydro-homophenylalanine was possible using the Ugi four-component reaction; meanwhile, the Passerini three-component reaction produces the β-enamide preferably.

Graphical abstract: Ugi and Passerini reactions enable the incorporation of ΔAA into N-alkylated peptides and depsipeptides

Supplementary files

Article information

Article type
Paper
Submitted
29 Marts 2022
Accepted
12 Maijs 2022
First published
12 Maijs 2022

New J. Chem., 2022,46, 11502-11509

Ugi and Passerini reactions enable the incorporation of ΔAA into N-alkylated peptides and depsipeptides

O. Concepción, F. J. Peñaloza, J. J. López, G. Cabrera-Barjas, C. A. Jiménez, M. W. Paixão and A. F. de la Torre, New J. Chem., 2022, 46, 11502 DOI: 10.1039/D2NJ01545E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements