有机化学 ›› 2026, Vol. 46 ›› Issue (1): 189-198.DOI: 10.6023/cjoc202506011 上一篇    下一篇

研究论文

半胱氨酸的硫杂芳基化反应

张鑫, 李飞, 周晨星, 霍聪德*()   

  1. 西北师范大学化学化工学院 兰州 730070
  • 收稿日期:2025-06-05 修回日期:2025-08-13 发布日期:2025-09-11
  • 通讯作者: 霍聪德
  • 基金资助:
    国家自然科学基金(22271234)

S-Heteroarylation of Cysteines

Zhang Xin, Li Fei, Zhou Chenxing, Huo Congde*()   

  1. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
  • Received:2025-06-05 Revised:2025-08-13 Published:2025-09-11
  • Contact: Huo Congde
  • Supported by:
    National Natural Science Foundation of China(22271234)

开发了一种利用廉价、易得的氯代杂芳烃, 对半胱氨酸衍生物进行S-杂芳基化的新方法. 该方法基于亲核芳香取代(SNAr)反应机制, 具有操作简便、反应条件温和的优势, 同时展现出优异的官能团兼容性与化学选择性. 底物普适性考察结果表明, 涵盖多种N-保护基的半胱氨酸衍生物、含半胱氨酸的寡肽及各类氯代杂芳烃在内的底物, 均可通过该方法顺利转化, 获得良好产率. 放大实验进一步验证了该方法的实用性和绿色经济性. 该策略为温和条件下高效、选择性地修饰半胱氨酸及其他硫醇分子提供了新途径, 在蛋白质修饰和生物分子标记等领域展现出广阔的应用前景.

关键词: 半胱氨酸, 杂芳基化,

A new method for S-heteroarylation of cysteine derivatives using affordable, readily available chlorinated hetero- aromatic compounds has been proposed. The reaction proceeds via nucleophilic aromatic substitution (SNAr) under mild conditions and simple operation, exhibiting excellent tolerance to various functional groups and high chemical selectivity. The results of substrate scope investigation demonstrated that A wide range of substrates, including different N-protected cysteine derivatives, cysteine-containing peptides, and various chlorinated heteroaryl compounds, could be efficiently transformed via this protocol to afford the desired products in good yields. Scale-up experiments confirmed the practicality and eco-friendliness of this protocol. Overall, this strategy offers an efficient and selective approach to modify cysteine and other thiols under mild conditions with broad potential applications in protein modification and biomolecular labeling.

Key words: cysteine, heteroarylation, peptide