Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in   Living Cells

doi:10.1002/anie.201608009

CORC > 北京大学 > 化学与分子工程学院

	Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells
	Fan, Xinyuan ; Ge, Yun ; Lin, Feng ; Yang, Yi ; Zhang, Gong ; Ngai, William Shu Ching ; Lin, Zhi ; Zheng, Siqi ; Wang, Jie ; Zhao, Jingyi ; Li, Jie ; Chen, Peng R.
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2016
关键词	amino acids decaging Diels-Alder reactions protein activation protein engineering UNNATURAL AMINO-ACIDS TRANS-CYCLOOCTENE LIGHT ACTIVATION PROTEIN FUNCTION CLICK CHEMISTRY SMALL MOLECULES LIGATION CYCLOADDITIONS CONJUGATION REACTIVITY
DOI	10.1002/anie.201608009
英文摘要	The inverse-electron-demand Diels-Alder (iDA) reaction has recently been repurposed as a bioorthogonal decaging reaction by accelerating the elimination process after an initial cycloaddition between trans-cyclooctene (TCO) and tetrazine (TZ). Herein, we systematically surveyed 3,6-substituted TZ derivatives by using a fluorogenic TCO-coumarin reporter followed by LC-MS analysis, which revealed that the initial iDA cycloaddition step was greatly accelerated by electron-withdrawing groups (EWGs) while the subsequent elimination step was strongly suppressed by EWGs. In addition, smaller substituents facilitated the decaging process. These findings promoted us to design and test unsymmetric TZs bearing an EWG group and a small non-EWG group at the 3- and 6-position, respectively. These TZs showed remarkably enhanced decaging rates, enabling rapid iDA-mediated protein activation in living cells.; National Key Research and Development Program [2016YFA0501500]; National Natural Science Foundation of China [21225206, 21432002, 21521003]; Center for Life Sciences (CLS); China Postdoctoral Science Foundation [2016M591004]; SCI(E); PubMed; ARTICLE; pengchen@pku.edu.cn; 45; 14046-14050; 55
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/457217]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Fan, Xinyuan,Ge, Yun,Lin, Feng,et al. Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2016.
APA	Fan, Xinyuan.,Ge, Yun.,Lin, Feng.,Yang, Yi.,Zhang, Gong.,...&Chen, Peng R..(2016).Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
MLA	Fan, Xinyuan,et al."Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016).