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Suzuki Cross‐Coupling Reaction with Genetically Encoded Fluorosulfates for Fluorogenic Protein Labeling
Author(s) -
Zhao Qian,
Guo Guoying,
Zhu Weiwei,
Zhu Liping,
Da Yifan,
Han Ying,
Xu Hongjiao,
Wu Shuohan,
Cheng Yaping,
Zhou Yani,
Cai Xiaoqing,
Jiang Xianxing
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002037
Subject(s) - biocompatibility , green fluorescent protein , coupling reaction , chemistry , fluorescence , aqueous medium , tyrosine , aryl , combinatorial chemistry , coupling (piping) , catalysis , aqueous solution , biophysics , biochemistry , materials science , biology , organic chemistry , gene , physics , alkyl , quantum mechanics , metallurgy
A palladium‐catalyzed cross‐coupling reaction with aryl halide functionalities has recently emerged as a valuable tool for protein modification. Herein, a new fluorogenic modification methodology for proteins, with genetically encoded fluorosulfate‐ l ‐tyrosine, which exhibits high efficiency and biocompatibility in bacterial cells as well as in aqueous medium, is described. Furthermore, the cross‐coupling of 4‐cyanophenylboronic acid on green fluorescent protein was shown to possess a unique fluorogenic property, which could open up the possibility of a responsive “off/on” switch with great potential to enable spectroscopic imaging of proteins with minimal background noise. Taken together, a convenient and efficient catalytic system has been developed that may provide broad utilities in protein visualization and live‐cell imaging.