title: Design of spiro[2.3]hex-1-ene, a genetically encodable double-strained alkene for superfast photoclick chemistry.
abstract: Reactive yet stable alkene reporters offer a facile route to studying fast biological processes via the cycloaddition-based bioorthogonal reactions. Here, we report the design and synthesis of a strained spirocyclic alkene, spiro[2.3]hex-1-ene (Sph), for an accelerated photoclick chemistry, and its site-specific introduction into proteins via amber codon suppression using the wild-type pyrrolysyl-tRNA synthetase/tRNA(CUA) pair. Because of its high ring strain and reduced steric hindrance, Sph exhibited fast reaction kinetics (k2 up to 34,000 M(-1) s(-1)) in the photoclick chemistry and afforded rapid (<10 s) bioorthogonal protein labeling.
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Zhipeng
authors.initials: Z
authors.lastname: Yu
authors.forename: Qing
authors.initials: Q
authors.lastname: Lin
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D057930:Click Chemistry; D053138:Cyclohexenes / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D055668:Photochemical Processes; D011789:Quantum Theory; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D053138:Cyclohexenes; D013141:Spiro Compounds