Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry

John C. Jewett; Carolyn R. Bertozzi

doi:10.1021/ol2025026

Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry

John C. Jewett, Carolyn R. Bertozzi

Research output: Contribution to journal › Article › peer-review

93 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	5937-5939
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	22
DOIs	https://doi.org/10.1021/ol2025026
State	Published - Nov 18 2011
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol2025026

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abstract = "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.",

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AU - Bertozzi, Carolyn R.

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AB - 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.

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Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry

Abstract

ASJC Scopus subject areas

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