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†

Xuekang Cai,‡^ab Dan Wang,‡^c Yasi Gao,^b Long Yi,

^bd Xing Yang

*^ae and Zhen Xi*^cd

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* Corresponding authors

^a Department of Nuclear Medicine, Peking University First Hospital, Beijing, China
E-mail: yangxing2017@bjmu.edu.cn

^b State Key Laboratory of Organic–Inorganic Composites, Beijing University of Chemical Technology, 15 Beisanhuan East Road, Chaoyang District, Beijing 100029, China

^c State Key Laboratory of Elemento-Organic Chemistry, Department of Chemical Biology, National Pesticide Engineering Research Center (Tianjin), Nankai University, Tianjin, China
E-mail: zhenxi@nankai.edu.cn
Tel: +86 22 23504782

^d Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), China

^e Peking University School of Medical Technology, Beijing, 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.

This article is part of the themed collection: Editors' collection: Chemical Biology

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DOI: https://doi.org/10.1039/C8RA09303B
Article type: Paper
Submitted: 11 Nov 2018
Accepted: 10 Dec 2018
First published: 19 Dec 2018
This article is Open Access

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RSC Adv., 2019,9, 23-26

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

X. Cai, D. Wang, Y. Gao, L. Yi, X. Yang and Z. Xi, RSC Adv., 2019, 9, 23 DOI: 10.1039/C8RA09303B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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

Abstract

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

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