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Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells
Fan, Xinyuan1,2; Ge, Yun1; Lin, Feng1; Yang, Yi1; Zhang, Gong1,2; Ngai, William Shu Ching1; Lin, Zhi1; Zheng, Siqi1; Wang, Jie1,2; Zhao, Jingyi1,2; Li, Jie1; Chen, Peng R.1,2
KeywordAmino Acids Decaging Diels-alder Reactions Protein Activation Protein Engineering
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2016-11-02
ISSN1433-7851
DOI10.1002/anie.201608009
Volume55Issue:45Pages:14046-14050
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordUNNATURAL AMINO-ACIDS ; TRANS-CYCLOOCTENE ; LIGHT ACTIVATION ; PROTEIN FUNCTION ; CLICK CHEMISTRY ; SMALL MOLECULES ; LIGATION ; CYCLOADDITIONS ; CONJUGATION ; REACTIVITY
AbstractThe 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.
Language英语
WOS IDWOS:000387016200024
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Cited Times:45[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/169813
Collection中国科学院大连化学物理研究所
Corresponding AuthorChen, Peng R.
Affiliation1.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci,Minist Educ, Coll Chem & Mol Engn,Synthet & Funct Biomol Ctr, Beijing 100871, Peoples R China
2.Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China
Recommended Citation
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,2016,55(45):14046-14050.
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,55(45),14046-14050.
MLA Fan, Xinyuan,et al."Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55.45(2016):14046-14050.
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