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Novel electrochemically-mediated peptide dethiylation in processes relevant to native chemical ligation

Lamb, Charles MG; Shi, Jian; Wilden, Jonathan D; Macmillan, Derek; (2022) Novel electrochemically-mediated peptide dethiylation in processes relevant to native chemical ligation. Organic & Biomolecular Chemistry , 36 (20) pp. 7343-7350. 10.1039/d2ob01499h. Green open access

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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.

Type: Article
Title: Novel electrochemically-mediated peptide dethiylation in processes relevant to native chemical ligation
Location: England
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/d2ob01499h
Publisher version: https://doi.org/10.1039/D2OB01499H
Language: English
Additional information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence
Keywords: Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, ACYL TRANSFER, CYSTEINE, OXIDATION, PROTEINS, CLEAVAGE, GLYCINE
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL
URI: https://discovery.ucl.ac.uk/id/eprint/10156008
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