ArticleJournal of the American Chemical Society2014
Design of spiro[2.3]hex-1-ene, a genetically encodable double-strained alkene for superfast photoclick chemistry.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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Who cites it
40 citing papers in PubMed.
- Site-Specific Protein Bioconjugation Through Cellular Incorporation of Noncanonical Amino Acids.Angewandte Chemie (International ed. in English) · 2026Review
- Toward Chromoselective Transformations in Biological Systems: Perspectives and Challenges.Angewandte Chemie (International ed. in English) · 2026Review
- Cyclopropenes in Photochemical Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Engineering Pyrrolysine Systems for Genetic Code Expansion and Reprogramming.Chemical reviews · 2024Review
- Metabolic labelling of DNA in cells by means of the "photoclick" reaction triggered by visible light.RSC chemical biology · 2023Article
- Seeking Citius: Photochemical Access of Reactive Intermediates for Faster Bioorthogonal Reactions.Chembiochem : a European journal of chemical biology · 2022Article
- Dual fluorescent labeling of GLP-1R in live cellsRSC chemical biology · 2022Article
- Expanding the functionality of proteins with genetically encoded dibenzo[Chemical science · 2022Article
- Catalytic Activation of Bioorthogonal Chemistry with Light (CABL) Enables Rapid, Spatiotemporally Controlled Labeling and No-Wash, Subcellular 3D-Patterning in Live Cells Using Long Wavelength Light.Journal of the American Chemical Society · 2022Article
- Superfast Tetrazole-BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells.Journal of the American Chemical Society · 2022Article
- Intracellular bioorthogonal labeling of glucagon receptor via tetrazine ligation.Bioorganic & medicinal chemistry · 2021Article
- EnablingJournal of the American Chemical Society · 2021Article
- Photoclick Chemistry: A Bright Idea.Chemical reviews · 2021Review
- Light-Triggered Click Chemistry.Chemical reviews · 2021Review
- Oxidation-Induced "One-Pot" Click Chemistry.Chemical reviews · 2021Article
- Bioorthogonal chemistry.Nature reviews. Methods primers · 2021Article
- Direct ring-strain loading for visible-light accelerated bioorthogonal ligation via diarylsydnone-dibenzo[b,f ][1,4,5]thiadiazepine photo-click reactions.Communications chemistry · 2020Article
- Fluorescent bioorthogonal labeling of class B GPCRs in live cells.Methods in enzymology · 2020Article
- Developing bioorthogonal probes to span a spectrum of reactivities.Nature reviews. Chemistry · 2020Article
- Fitness Factors for Bioorthogonal Chemical Probes.ACS chemical biology · 2019Article
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2 authors.
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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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