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Fluorodibenzocyclooctynes: A Trackable Click Reagent with Enhanced Reactivity.

Bioorthogonal reactions have widespread applications in biological systems, and development of new bioorthogonal reactions has been of great interest over the past two decades. Herein we report the design and synthesis of a family of fluorinated dibenzocyclooctynes (FDIBOs). The electron-deficient nature of fluorine atoms significantly accelerated the reaction of cyclooctynes in 1,3-dipolar cycloadditions, with either benzyl azide or ethyl diazoacetate, comparing to conventional dibenzocyclooctyne (DIBO). In addition, FDIBOs showed unique trackable properties, because of the high NMR sensitivity of naturally abundant 19F isotope. Biological molecules, including monosaccharide, peptide, and protein were tested with FDIBOs, and these reactions could be easily monitored by 19F NMR to evaluate the progress of conjugation reactions. In addition, labeling of live cells was also demonstrated with metabolically modified bacteria to expand the possible applications of FDIBOs.