Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 19, Pages 4212-4217Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00830a
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Funding
- NSFC [21302010, 21402007, 21572019]
- 111 project [B14004]
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The development of efficient bioorthogonal reactions for sensing of endogenous biomolecules and for bioconjugation should be of paramount importance in the field of chemical biology. In this work, the o,o'-difluorinated aromatic azide was firstly employed to develop a new fast-response fluorescent probe 1 for H2S detection and for bioorthogonal reactions. Compared with non- and mono-fluorinated probes, 1 showed faster reaction toward H2S, the third gasotransmitter, in buffer (pH 7.4), implying that the reaction rate could be enhanced by the dual-fluorine groups. Furthermore, such enhanced reaction rates of 1 were also observed in the Staudinger reaction and strain-promoted azide-alkyne cycloaddition (SPAAC) based on the comparison studies of the non- fluorinated probe. Our results firstly highlight that the o,o'-difluorinated aromatic azide group should be useful for fast bioorthogonal reactions and H2S detection.
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