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

[Image: see text] 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 c...

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Autores principales: Yu, Zhipeng, Lin, Qing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971965/
https://www.ncbi.nlm.nih.gov/pubmed/24592808
http://dx.doi.org/10.1021/ja5012542
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author Yu, Zhipeng
Lin, Qing
author_facet Yu, Zhipeng
Lin, Qing
author_sort Yu, Zhipeng
collection PubMed
description [Image: see text] 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 (k(2) up to 34 000 M(–1) s(–1)) in the photoclick chemistry and afforded rapid (<10 s) bioorthogonal protein labeling.
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spelling pubmed-39719652015-03-04 Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry Yu, Zhipeng Lin, Qing J Am Chem Soc [Image: see text] 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 (k(2) up to 34 000 M(–1) s(–1)) in the photoclick chemistry and afforded rapid (<10 s) bioorthogonal protein labeling. American Chemical Society 2014-03-04 2014-03-19 /pmc/articles/PMC3971965/ /pubmed/24592808 http://dx.doi.org/10.1021/ja5012542 Text en Copyright © 2014 American Chemical Society
spellingShingle Yu, Zhipeng
Lin, Qing
Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry
title Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry
title_full Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry
title_fullStr Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry
title_full_unstemmed Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry
title_short Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry
title_sort design of spiro[2.3]hex-1-ene, a genetically encodable double-strained alkene for superfast photoclick chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971965/
https://www.ncbi.nlm.nih.gov/pubmed/24592808
http://dx.doi.org/10.1021/ja5012542
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AT linqing designofspiro23hex1eneageneticallyencodabledoublestrainedalkeneforsuperfastphotoclickchemistry

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