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Isomeric Cyclopropenes Exhibit Unique Bioorthogonal Reactivities

2013; American Chemical Society; Volume: 135; Issue: 37 Linguagem: Inglês

10.1021/ja407737d

1943-2984

David N. Kamber, Lidia Nazarova, Yong Liang, Steven A. Lopez, David M. Patterson, Hui‐Wen Shih, K. N. Houk, Jennifer A. Prescher,

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.