Electro-induced C-H/S-H cross-coupling for the functionalization/macrocyclization of cysteine-containing peptides

Fang Xiang, Jia Deng, Xiaotong Bu, Youjun Zhou, Jianrong Zhang, Yue Weng and Meng Gao ()
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Fang Xiang: Hubei University
Jia Deng: LTD
Xiaotong Bu: Hubei University
Youjun Zhou: Hubei University
Jianrong Zhang: Hubei University
Yue Weng: Hubei University
Meng Gao: Hubei University

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract Herein, an electro-induced umpolung approach that enables the efficient functionalization/macrocyclization of cysteine-containing peptides is reported. Notably, this method utilizes simple halogen source and takes metal-mediated halogen atom transfer as the main pathway to enable the in-situ polarity reversal, highlighting the unique possibilities associated with electrochemical activation methods. Under simple and mild conditions, cysteine residue can be well-labelled with high chemo-selectivity and excellent conversion. This transformation can tolerate a wide range of valuable enamines, azoles, and peptides partners, and can also be utilized as a macrocyclization tactic for cyclic peptide synthesis and other areas.

Date: 2025
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DOI: 10.1038/s41467-025-64615-4

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