Zhicheng Yan, Yiyao Pan, Guofeng Jiao, Mengyu Xu, Dongguang Fan, Ziwei Hu, Jiarui Wu, Tao Chen, Miao Liu, Xiaoguang Bao, Hengte Ke, Xingyue Ji
Bioorthogonal decaging chemistry with both fast kinetics and high efficiency is highly demanded for in vivo applications but remains very sporadic. Herein, we describe a new bioorthogonal decaging chemistry between N -oxide and silylborane. A simple replacement of "C" in boronic acid with "Si" was able to substantially accelerate the N -oxide decaging kinetics by 106 fold ( k 2 : up to 103 M-1 s-1 ). Moreover, a new N -oxide-masked self-immolative spacer was developed for the traceless release of various payloads upon clicking with silylborane with fast kinetics and high efficiency (>90%)...
November 7, 2023: Journal of the American Chemical Society