β-Carbonyl sulfonium enables cysteine-specific bioconjugation for activity-based protein profiling in live cells

Chuan Wan; Dongyan Yang; Xiaochun Guo; Tuanjie Zhang; Zhijun Ruan; Chuan Dai; Yun Xing; Feng Yin; Rui Wang; Zigang Li

doi:10.1039/D4CC00295D

β-Carbonyl sulfonium enables cysteine-specific bioconjugation for activity-based protein profiling in live cells†

Chuan Wan,‡^c Dongyan Yang,‡^d Xiaochun Guo,‡^a Tuanjie Zhang,^b Zhijun Ruan,^b Chuan Dai,^b Yun Xing,^a Feng Yin,*^ab 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: yinfeng@pkusz.edu.cn, lizg@pkusz.edu.cn

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

^c College of Health Science and Environmental Engineering, Shenzhen Technology University, Shenzhen, P. R. China

^d Innovative Institute for Plant Health, College of Chemistry and Chemical Engineering, Zhongkai University of Agriculture and Engineering, Guangzhou, P. R. China

Abstract

Chemical labeling methods for proteins are highly researched. Herein, we introduced β-carbonyl sulfonium compounds for selective cysteine modification in proteins within biological systems. Structural tuning led to sulfonium-based probes with high reactivity and selectivity. These probes show excellent biocompatibility, cell uptake, and specificity towards cysteine profiling in live cells.

Chemical Communications

β-Carbonyl sulfonium enables cysteine-specific bioconjugation for activity-based protein profiling in live cells†

Abstract

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β-Carbonyl sulfonium enables cysteine-specific bioconjugation for activity-based protein profiling in live cells

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