Triazine-pyridine chemistry for protein labelling on tyrosine

Hongfei Jiang; Qing Zhang; Yue Zhang; Huxin Feng; Hao Jiang; Fan Pu; Rilei Yu; Zheng Zhong; Chaoming Wang; Yi Man Eva Fung; Pilar Blasco; Yongxin Li; Tao Jiang; Xuechen Li

doi:10.1039/D2CC01528E

Triazine-pyridine chemistry for protein labelling on tyrosine†

Hongfei Jiang,‡^a Qing Zhang,‡*^b Yue Zhang,‡^b Huxin Feng,^a Hao Jiang,^a Fan Pu,^b Rilei Yu,

^a Zheng Zhong,

^b Chaoming Wang,^a Yi Man Eva Fung,

^b Pilar Blasco,^b Yongxin Li,^b Tao Jiang

*^a and Xuechen Li

*^b

Author affiliations

* Corresponding authors

^a Key Laboratory of Marine Drugs Chinese Ministry of Education, Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
E-mail: jiangtao@ouc.edu.cn

^b Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China
E-mail: xuechenl@hku.hk, zhangqing7864@163.com

Abstract

Herein, we discover the new reactivity of the 1,3,5-triazine moiety reacting with a phenol group and report the development of biocompatible and catalyst-free triazine-pyridine chemistry (TPC) for tyrosine labelling under physiological conditions and profiling in the whole proteome. TPC exhibited high tyrosine chemoselectivity in biological systems after cysteine blocking, displayed potential in tyrosine-guided protein labelling, and had bio-compatibility in live cells.

This article is part of the themed collection: 2022 Pioneering Investigators

Chemical Communications

Triazine-pyridine chemistry for protein labelling on tyrosine†

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Triazine-pyridine chemistry for protein labelling on tyrosine

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