Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells
文献类型：期刊论文
| 作者 | Ge, Yun1; Zheng, Siqi1; Zhao, Jingyi1,2; Wang, Jie1,2; Chen, Peng R.1,2; Li, Jie1; Fan, Xinyuan1,2; Lin, Feng1; Yang, Yi1; Zhang, Gong1,2 |
| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2016-11-02 |
| 卷号 | 55期号:45页码:14046-14050 |
| 关键词 | Amino Acids Decaging Diels-alder Reactions Protein Activation Protein Engineering |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.201608009 |
| 文献子类 | Article |
| 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. |
| WOS关键词 | UNNATURAL AMINO-ACIDS ; TRANS-CYCLOOCTENE ; LIGHT ACTIVATION ; PROTEIN FUNCTION ; CLICK CHEMISTRY ; SMALL MOLECULES ; LIGATION ; CYCLOADDITIONS ; CONJUGATION ; REACTIVITY |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000387016200024 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://cas-ir.dicp.ac.cn/handle/321008/169812]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 通讯作者 | Chen, Peng R. |
| 作者单位 | 1.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 |
| 推荐引用方式 GB/T 7714 | Ge, Yun,Zheng, Siqi,Zhao, Jingyi,et al. Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2016,55(45):14046-14050. |
| APA | Ge, Yun.,Zheng, Siqi.,Zhao, Jingyi.,Wang, Jie.,Chen, Peng R..,...&Lin, Zhi.(2016).Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,55(45),14046-14050. |
| MLA | Ge, Yun,et al."Optimized Tetrazine Derivatives for Rapid Bioorthogonal Decaging in Living Cells".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55.45(2016):14046-14050. |
入库方式： OAI收割
来源：大连化学物理研究所
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