Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry | Zendy

Zhipeng Yu | Zendy; Qing Lin | Zendy

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Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry

Author(s) -

Zhipeng Yu,

Qing Lin

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja5012542

Subject(s) - bioorthogonal chemistry , alkene , chemistry , ene reaction , steric effects , cycloaddition , stereochemistry , click chemistry , ring strain , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis

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.

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