The thiol-sulfoxonium ylide photo-click reaction for bioconjugation

Chuan Wan; Zhanfeng Hou; Dongyan Yang; Ziyuan Zhou; Hongkun Xu; Yuena Wang; Chuan Dai; Mingchan Liang; Jun Meng; Jiean Chen; Feng Yin; Rui Wang; Zigang Li

doi:10.1039/D2SC05650J

The thiol-sulfoxonium ylide photo-click reaction for bioconjugation†

Chuan Wan,‡^a Zhanfeng Hou,‡^a Dongyan Yang,‡^c Ziyuan Zhou,^d Hongkun Xu,^a Yuena Wang,^a Chuan Dai,

^a Mingchan Liang,^b Jun Meng,^d Jiean Chen,

^b Feng Yin,

*^b Rui Wang*^b and Zigang Li

*^ab

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* Corresponding authors

^a State Key Laboratory of Chemical Oncogenomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, P. R. China
E-mail: lizg.sz@pku.edu.cn, lizg@szbl.ac.cn

^b Pingshan Translational Medicine Center, Shenzhen Bay Laboratory, Shenzhen, P. R. China
E-mail: wangrui@szbl.ac.cn, yinfeng@szbl.ac.cn

^c College of Chemistry and Chemical Engineering, Zhongkai University of Agriculture and Engineering, Guangzhou, P. R. China

^d National Cancer Center/National Clinical Research Center for Cancer/Cancer Hospital & Shenzhen Hospital, Chinese Academy of Medical Sciences and Peking Union Medical College, Shenzhen, P. R. China

Abstract

Visible-light-mediated methods were heavily studied as a useful tool for cysteine-selective bio-conjugation; however, many current methods suffer from bio-incompatible reaction conditions and slow kinetics. To address these challenges, herein, we report a transition metal-free thiol-sulfoxonium ylide photo-click reaction that enables bioconjugation under bio-compatible conditions. The reaction is highly cysteine-selective and generally finished within minutes with naturally occurring riboflavin derivatives as organic photocatalysts. The catalysts and substrates are readily accessible and bench stable and have satisfactory water solubility. As a proof-of-concept study, the reaction was smoothly applied in chemo-proteomic analysis, which provides efficient tools to explore the druggable content of the human proteome.

Chemical Science

The thiol-sulfoxonium ylide photo-click reaction for bioconjugation†

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