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.
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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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