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Updated: Aug 29, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Novel electrochemically-mediated peptide dethiylation in processes relevant to native chemical ligation
Charles M G Lamb1, Jian Shi1, Jonathan D Wilden1
1Department of Chemistry, UCL, 20 Gordon Street, London, WC1H 0AJ, UK. d.macmillan@ucl.ac.uk.
Abstract:
Here we explore electrochemical dethiylation in processes relevant to Native Chemical Ligation (NCL). NCL's reliance on the redox active amino acid cysteine and β-mercaptamine derivatives suggests a potential role for electrochemistry. We show that the application of a 1 V potential to platinum electrodes in 0.15 M TCEP solution is sufficient to convert Cys to Ala in cyclic peptides, and to cleave the 2-mercapto-2-phenethyl class of acyl transfer auxiliary.

