Tetra-fluorinated aromatic azide for highly efficient bioconjugation in living cells

Xuekang Cai; Dan Wang; Yasi Gao; Long Yi; Xing Yang; Zhen Xi

doi:10.1039/c8ra09303b

Tetra-fluorinated aromatic azide for highly efficient bioconjugation in living cells

RSC Adv. 2018 Dec 19;9(1):23-26. doi: 10.1039/c8ra09303b.

Authors

Xuekang Cai^{1

2}, Dan Wang³, Yasi Gao², Long Yi^{2

4}, Xing Yang^{1

5}, Zhen Xi^{3

4}

Affiliations

¹ Department of Nuclear Medicine, Peking University First Hospital Beijing 100034 China yangxing2017@bjmu.edu.cn.
² State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology 15 Beisanhuan East Road, Chaoyang District Beijing 100029 China.
³ State Key Laboratory of Elemento-Organic Chemistry, Department of Chemical Biology, National Pesticide Engineering Research Center (Tianjin), Nankai University Tianjin 300071 China zhenxi@nankai.edu.cn +86 22 23504782.
⁴ Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) China.
⁵ Peking University School of Medical Technology Beijing 100191 China.

Abstract

We developed a fast strain-promoted azide-alkyne cycloaddition reaction (SPAAC) by tetra-fluorinated aromatic azide with a kinetic constant of 3.60 M^-1 s^-1, which is among the fastest SPAAC ligations reported so far. We successfully employed the reaction for covalent labelling of proteins with high efficiency and for bioimaging of mitochondria in living cells. The reaction could be a generally useful toolbox for chemical biology and biomaterials.