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

被引：103

作者：

Yu, Zhipeng ^{[1
]}

Lin, Qing ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 11期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

BIOORTHOGONAL CHEMISTRY; MAMMALIAN-CELLS; LIVING CELLS; CYCLOADDITIONS; BICYCLONONYNES; CYCLOPROPENES; SPIROPENTENE; CYCLOOCTYNES; LIGATION; PROTEINS;

D O I：

10.1021/ja5012542

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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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收藏

页码：4153 / 4156

页数：4

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