Synthesis of a Fluorogenic Cyclooctyne Activated by Cu-Free Click Chemistry

被引：83

作者：

Jewett, John C.

Bertozzi, Carolyn R. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 22期

基金：

美国国家卫生研究院;

关键词：

STAUDINGER LIGATION; LIVING CELLS; COPPER-FREE; CYCLOADDITIONS; MODULATION; PROBE;

D O I：

10.1021/ol2025026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclooctyne-based probes that become fluorescent upon reaction with azides are important targets for real-time imaging of azide-labeled biomolecules. The concise synthesis of a coumarin-conjugated cyclooctyne, coumBARAC, that undergoes a 10-fold enhancement in fluorescence quantum yield upon triazole formation with organic azides is reported. The design principles embodied in coumBARAC establish a platform for generating fluorogenic cyclooctynes suited for biological imaging.

引用

页码：5937 / 5939

页数：3

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