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The tryptophan connection: cyclic peptide natural products linked via the tryptophan side chain
Jonathan A Swain1, Stephen R Walker1, Matthew B Calvert1
1School of Chemical Sciences, The University of Auckland, Symonds Street, Auckland 1010, New Zealand. m.brimble@auckland.ac.nz.
Abstract:
Covering: from 1938 up to March 2021The 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.
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