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

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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

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Article information


Submitted
03 Oct 2019
Accepted
12 Dec 2019
First published
12 Dec 2019

Chem. Commun., 2020, Advance Article
Article type
Communication

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, Advance Article , DOI: 10.1039/C9CC07783A

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