Isomeric Cyclopropenes Exhibit Unique Bioorthogonal Reactivities

作者：David N. Kamber, Lidia Nazarova, Yong Liang, Steven A. Lopez, David M. Patterson, Hui‐Wen Shih, K. N. Houk, Jennifer A. Prescher · 发表于：Journal of the American Chemical Society · 年份：2013 · DOI：10.1021/ja407737d · 被引用次数：156 · 研究领域：Click Chemistry and Applications、Cyclopropane Reaction Mechanisms、Chemical Synthesis and Analysis

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-Alder 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.