Control and Design of Mutual Orthogonality in Bioorthogonal Cycloadditions

被引：126
作者：
Liang, Yong [1 ]
Mackey, Joel L. [1 ]
Lopez, Steven A. [1 ]
Liu, Fang [1 ]
Houk, K. N. [1 ]
机构：
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 43期
基金：
美国国家科学基金会;
关键词：
FREE CLICK CHEMISTRY; DIELS-ALDER REACTIONS; STATE DISTORTION ENERGIES; COPPER-FREE; LIVING CELLS; 1,3-DIPOLAR CYCLOADDITIONS; TETRAZINE CYCLOADDITIONS; DENSITY FUNCTIONALS; TRANS-CYCLOOCTENES; REACTIVITY;
D O I：
10.1021/ja309241e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The azide-dibenzocyclooctyne and trans-cyclooctene-tetrazine cycloadditions are both bioorthogonal and mutually orthogonal: trans-cyclooctene derivatives greatly prefer to react with tetrazines rather than azides, while dibenzocyclooctyne derivatives react with azides but not with tetrazines under physiological conditions. DFT calculations used to identify the origins of this extraordinary selectivity are reported, and design principles to guide discovery of new orthogonal cycloadditions are proposed. Two new bioorthogonal reagents, methylcyclopropene and 3,3,6,6-tetramethylthiacycloheptyne, are predicted to be mutually orthogonal in azide and tetrazine cycloadditions.
引用
收藏
页码：17904 / 17907
页数：4
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