title: Isomeric cyclopropenes exhibit unique bioorthogonal reactivities.
abstract: 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.
authors.affiliation: Departments of †Chemistry, ‡Molecular Biology & Biochemistry, and §Pharmaceutical Science, University of California , Irvine, California 92697, United States.
authors.forename: David N
authors.initials: DN
authors.lastname: Kamber
authors.forename: Lidia A
authors.initials: LA
authors.lastname: Nazarova
authors.forename: Yong
authors.initials: Y
authors.lastname: Liang
authors.forename: Steven A
authors.initials: SA
authors.lastname: Lopez
authors.forename: David M
authors.initials: DM
authors.lastname: Patterson
authors.forename: Hui-Wen
authors.initials: HW
authors.lastname: Shih
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Prescher
mesh_terms: D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure; D013777:Tetrazoles / Q000737:chemistry
chemical_list: C549579:1,2-di-tert-butyl-3,3-dimethylcyclopropene; D003521:Cyclopropanes; D013777:Tetrazoles