期刊
CHEMICAL SCIENCE
卷 11, 期 37, 页码 10175-10179出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc03216f
关键词
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资金
- ERC Starting Grant of the European Research Council [ERC-2014-StG-639005]
- Netherlands Organization for Scienti.c Research (NWO)-CW-ECHO Grant program 2016
The inverse electron-demand Diels-Alder (IEDDA) pyridazine elimination is one of the key bioorthogonal bond-breaking reactions. In this reactiontrans-cyclooctene (TCO) serves as a tetrazine responsive caging moiety for amines, carboxylic acids and alcohols. One issue to date has been the lack of synthetic methods towards TCO ethers from functionalized (aliphatic) alcohols, thereby restricting bioorthogonal utilization. Two novel reagents were developed to enable controlled formation ofcis-cyclooctene (CCO) ethers, followed by optimized photochemical isomerization to obtain TCO ethers. The method was exemplified by the controlled bioorthogonal activation of thelacoperon system inE. coliusing a TCO-ether-modified carbohydrate inducer.
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