Issue 3, 2023

The thiol-sulfoxonium ylide photo-click reaction for bioconjugation


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.

Graphical abstract: The thiol-sulfoxonium ylide photo-click reaction for bioconjugation

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Article information

Article type
Edge Article
12 Oct 2022
01 Dec 2022
First published
03 Dec 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 604-612

The thiol-sulfoxonium ylide photo-click reaction for bioconjugation

C. Wan, Z. Hou, D. Yang, Z. Zhou, H. Xu, Y. Wang, C. Dai, M. Liang, J. Meng, J. Chen, F. Yin, R. Wang and Z. Li, Chem. Sci., 2023, 14, 604 DOI: 10.1039/D2SC05650J

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