Issue 2, 2022

The tryptophan connection: cyclic peptide natural products linked via the tryptophan side chain

Abstract

Covering: from 1938 up to March 2021

The electron-rich indole side chain of tryptophan is a versatile substrate for peptide modification. Upon the action of various cyclases, the tryptophan side chain may be linked to a nearby amino acid residue, opening the door to a diverse range of cyclic peptide natural products. These compounds exhibit a wide array of biological activity and possess fascinating molecular architectures, which have made them popular targets for total synthesis studies. This review examines the isolation and bioactivity of tryptophan-linked cyclic peptide natural products, along with a discussion of their first total synthesis, and biosynthesis where this has been studied.

Graphical abstract: The tryptophan connection: cyclic peptide natural products linked via the tryptophan side chain

Article information

Article type
Review Article
Submitted
28 Jun 2021
First published
28 Sep 2021

Nat. Prod. Rep., 2022,39, 410-443

The tryptophan connection: cyclic peptide natural products linked via the tryptophan side chain

J. A. Swain, S. R. Walker, M. B. Calvert and M. A. Brimble, Nat. Prod. Rep., 2022, 39, 410 DOI: 10.1039/D1NP00043H

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