Dearomatization–rearomatization strategy of tyrosine for peptide/protein modification through thiol-addition reactions

Pengxin Wang; Yulian Cheng; Chunlei Wu; Ruixiang Luo; Caibing Ma; Yimin Zhou; Zhilong Ma; Rui Wang; Wu Su; Lijing Fang

doi:10.1039/D1CC04191F

Dearomatization–rearomatization strategy of tyrosine for peptide/protein modification through thiol-addition reactions†

Pengxin Wang,^ab Yulian Cheng,^b Chunlei Wu,^b Ruixiang Luo,^b Caibing Ma,^b Yimin Zhou,^b Zhilong Ma,^b Rui Wang,

*^a Wu Su

*^b and Lijing Fang

*^b

Author affiliations

* Corresponding authors

^a Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, Gansu, China

^b Guangdong Key Laboratory of Nanomedicine, Institute of Biomedicine and Biotechnology, Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen, Guangdong 518055, China
E-mail: lj.fang@siat.ac.cn

Abstract

We have developed a dearomatization–rearomatization strategy for the modification of peptides/proteins through a thiol-Michael addition to the electrophilic cyclohexadienone intermediate that is generated in situ via the oxidation of tyrosine. This strategy enriches the conjugation toolbox and has great potential for applications in medicinal chemistry and chemical biology.

Chemical Communications

Dearomatization–rearomatization strategy of tyrosine for peptide/protein modification through thiol-addition reactions†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Dearomatization–rearomatization strategy of tyrosine for peptide/protein modification through thiol-addition reactions

Social activity

Search articles by author

Spotlight

Advertisements