Design and synthesis of cyclopropenes that exhibit unique bioorthogonal reactivitiesDavid N. Kamber1, Lidia A. Nazarova1, Yong Liang4, Steven A. Lopez4, David M. Patterson1, Hui-Wen Shih1, K. N. Houk4 , and Jennifer A. Prescher*1-3Departments of 1Chemistry, 2Molecular Biology & Biochemistry, and 3Pharmaceutical Science, University of California, Irvine, California 92697, United States4Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States Bioorthogonal chemistries enable the direct interrogation of glycans, lipids, and other biopolymers in live cells.  However, many bioorthogonal reactions are incompatible with one another and cannot be used in tandem to examine multiple biomolecules. We identified transformations with isomeric cyclopropenes that can be used concurrently to monitor biomolecules in living systems: the 1,3-dipolar cycloaddition of 3,3-disubstituted cyclopropenes with nitrile imines, and the inverse electron-demand Diels-Alder reaction of 1,3-disubstituted cyclopropenes with tetrazines.  Notably, the cyclopropenes used in these bioorthogonal reactions differ by the location of a single methyl group.  The disubstituted scaffolds are also small and compatible with cellular biosynthetic pathways.  Thus, we expect that the orthogonally reactive cyclopropenes will enable the direct monitoring of multi-component processes in live cells.

Design and synthesis of cyclopropenes that exhibit unique bioorthogonal reactivities

248th National Meeting (2014)

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