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Org Lett. 2011 Nov 18;13(22):5937-9. doi: 10.1021/ol2025026. Epub 2011 Oct 26.

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

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1
Department of Chemistry and Howard Hughes Medical Institute, University of California, Berkeley, California 94720, United States.

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.

PMID:
22029411
PMCID:
PMC3219546
DOI:
10.1021/ol2025026
[Indexed for MEDLINE]
Free PMC Article
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