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Updated: May 16, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Investigation of the ring-closing metathesis of peptides in water
Stephen A Cochrane1, Zedu Huang, John C Vederas
1Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
Abstract:
A systematic study of the ring-closing metathesis (RCM) of unprotected oxytocin and crotalphine peptide analogues in water is reported. The replacement of cysteine with S-allyl cysteine enables RCM to proceed readily in water containing excess MgCl(2) with 30% t-BuOH as a co-solvent. The presence of the sulfur atom is vital for efficient aqueous RCM to occur, with non-sulfur containing analogues undergoing RCM in low yields.
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