Wan Chuan, Hou Zhanfeng, Yang Dongyan, Zhou Ziyuan, Xu Hongkun, Wang Yuena, Dai Chuan, Liang Mingchan, Meng Jun, Chen Jiean, Yin Feng, Wang Rui, Li Zigang
State Key Laboratory of Chemical Oncogenomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School Shenzhen 518055 P. R. China
College of Chemistry and Chemical Engineering, Zhongkai University of Agriculture and Engineering Guangzhou 510225 P. R. China.
Chem Sci. 2022 Dec 3;14(3):604-612. doi: 10.1039/d2sc05650j. eCollection 2023 Jan 18.
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.
可见光介导的方法作为半胱氨酸选择性生物共轭的有用工具得到了深入研究；然而，许多现有方法存在生物不相容的反应条件和缓慢的动力学问题。为了应对这些挑战，在此我们报道了一种无过渡金属的硫醇-磺氧化钅内盐光点击反应，该反应能够在生物相容的条件下进行生物共轭。该反应具有高度的半胱氨酸选择性，通常在几分钟内就能完成，以天然存在的核黄素衍生物作为有机光催化剂。催化剂和底物易于获得且在实验台上稳定，并且具有令人满意的水溶性。作为概念验证研究，该反应顺利应用于化学蛋白质组学分析，为探索人类蛋白质组中的可药物化成分提供了有效的工具。
