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

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.

SUBMITTER: Jewett JC

PROVIDER: S-EPMC3219546 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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

Jewett John C JC Bertozzi Carolyn R CR

Organic letters 20111026 22

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. ...[more]

PMID: 22029411

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