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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.

SUBMITTER: Yu Z

PROVIDER: S-EPMC3971965 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Design of spiro[2.3]hex-1-ene, a genetically encodable double-strained alkene for superfast photoclick chemistry.

Yu Zhipeng Z Lin Qing Q

Journal of the American Chemical Society 20140310 11

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 ex ...[more]

PMID: 24592808

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