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

当前位置： X-MOL 学术 › J. Am. Chem. Soc. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Design of Spiro[2.3]hex-1-ene, a Genetically Encodable Double-Strained Alkene for Superfast Photoclick Chemistry
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2014-03-10 , DOI: 10.1021/ja5012542
Zhipeng Yu ₁ , Qing Lin

Affiliation

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/tRNACUA 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.

中文翻译：

Spiro[2.3]hex-1-ene 的设计，一种用于超快光点击化学的可遗传编码的双应变烯烃

反应性但稳定的烯烃报告分子通过基于环加成的生物正交反应为研究快速生物过程提供了一种简便的途径。在这里，我们报告了一种用于加速光点击化学的应变螺环烯烃 spiro[2.3]hex-1-ene (Sph) 的设计和合成，以及使用野生型通过琥珀密码子抑制将其位点特异性引入蛋白质吡咯赖氨酰-tRNA 合成酶/tRNACUA 对。由于其高环应变和减少的空间位阻，Sph 在光点击化学中表现出快速反应动力学（k2 高达 34 000 M–1 s–1），并提供快速（<10 s）生物正交蛋白质标记。

更新日期：2014-03-10

点击分享查看原文

点击收藏

公开下载

阅读更多本刊新发论文本刊介绍/投稿指南