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

Authors
  • Yu, Zhipeng1
  • Lin, Qing
  • 1 Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260, United States. , (United States)
Type
Published Article
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Publication Date
Mar 19, 2014
Volume
136
Issue
11
Pages
4153–4156
Identifiers
DOI: 10.1021/ja5012542
PMID: 24592808
Source
Medline
License
Unknown

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.

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