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<p>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.</p>

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

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年10月30日

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  • Fang Xiang,
  • Jia Deng,
  • Xiaotong Bu,
  • Youjun Zhou,
  • Jianrong Zhang,
  • Yue Weng,
  • Meng Gao

摘要

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.