A Biosynthetic Route to Photoclick Chemistry on Proteins

被引：115

作者：

Wang, Jiangyun ^{[1
]}

Zhang, Wei ^{[1
]}

Song, Wenjiao ^{[2
]}

Wang, Yizhong ^{[2
]}

Yu, Zhipeng ^{[2
]}

Li, Jiasong ^{[3
]}

Wu, Minhao ^{[3
]}

Wang, Lin ^{[3
]}

Zang, Jianye ^{[3
]}

Lin, Qing ^{[2
]}

机构：

[1] Chinese Acad Sci, Inst Biophys, Natl Key Lab Biomacromol, Beijing 100101, Peoples R China

[2] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

[3] Univ Sci & Technol China, Sch Life Sci, Hefei 230026, Anhui, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 42期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

TRANSFER-RNA SYNTHETASES; GENETIC-CODE; ESCHERICHIA-COLI; IN-VIVO; CROSS-LINKING; AMINO-ACID; STRUCTURAL BASIS; CELLS; FUNCTIONALIZATION; RHODOPSIN;

D O I：

10.1021/ja104350y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Light-induced chemical reactions exist in nature, regulating many important cellular and organismal functions, e.g., photosensing in prokaryotes and vision formation in mammals. Here, we report the genetic incorporation of a photoreactive unnatural amino acid, p-(2-tetrazole)phenylalanine (p-Tpa), into myoglobin site-specifically in E. coli by evolving an orthogonal tRNA/aminoacyl-tRNA synthetase pair and the use of p-Tpa as a bioorthogonal chemical "handle" for fluorescent labeling of p-Tpa-encoded myoglobin via the photoclick reaction. Moreover, we elucidated the structural basis for the biosynthetic incorporation of p-Tpa into proteins by solving the X-ray structure of p-Tpa-specific aminoacyl-tRNA synthetase in complex with p-Tpa. The genetic encoding of this photoreactive amino acid should make it possible in the future to photoregulate protein function in living systems.

引用

页码：14812 / 14818

页数：7

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