Isomeric Cyclopropenes Exhibit Unique Bioorthogonal Reactivities
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- 作者：David N. Kamber ; Lidia A. Nazarova ; Yong Liang ; Steven A. Lopez ; David M. Patterson ; Hui-Wen Shih ; K. N. Houk ; Jennifer A. Prescher
- 刊名：Journal of the American Chemical Society
- 出版年：2013
- 出版时间：September 18, 2013
- 年：2013
- 卷：135
- 期：37
- 页码：13680-13683
- 全文大小：310K
- 年卷期：v.135,no.37(September 18, 2013)
- ISSN：1520-5126
文摘
Bioorthogonal chemistries have provided tremendous insight into biomolecule structure and function. However, many popular bioorthogonal transformations are incompatible with one another, limiting their utility for studies of multiple biomolecules in tandem. We identified two reactions that can be used concurrently to tag biomolecules in complex environments: the inverse electron-demand Diels鈥揂lder reaction of tetrazines with 1,3-disubstituted cyclopropenes, and the 1,3-dipolar cycloaddition of nitrile imines with 3,3-disubstituted cyclopropenes. Remarkably, the cyclopropenes used in these transformations differ by the placement of a single methyl group. Such orthogonally reactive scaffolds will bolster efforts to monitor multicomponent processes in cells and organisms.