Issue 6, 2020

On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation

Abstract

On-resin intramolecular native chemical ligation (NCL) assisted by N-ethylcysteine using Fmoc/SPPS to obtain cyclic peptides is described. N-terminal cysteine-containing peptides were subjected to NCL conditions leading to cyclization–cleavage reactions and consecutive SN shift, rendering cyclic peptides in good yields and purities. The compounds were evaluated against P. falciparum 3D7.

Graphical abstract: On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation

Supplementary files

Article information

Article type
Communication
Submitted
03 okt 2019
Accepted
12 dec 2019
First published
12 dec 2019

Chem. Commun., 2020,56, 956-959

On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation

G. Serra, L. Posada and H. Hojo, Chem. Commun., 2020, 56, 956 DOI: 10.1039/C9CC07783A

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