Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry.
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.
Department of Chemistry and Howard Hughes Medical Institute, University of California, Berkeley, California 94720, United States.
John C
JC
Jewett
Carolyn R
CR
Bertozzi
D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D034242:Cyclooctanes / Q000138:chemical synthesis*; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D015394:Molecular Structure
D034242:Cyclooctanes; D005456:Fluorescent Dyes; D003300:Copper; C474479:cyclooctane