Journal
ORGANIC LETTERS
Volume 23, Issue 21, Pages 8477-8481Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03192
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Funding
- National Natural Science Foundation of China [22077031]
- Research Program of State Key Laboratory of Bioreactor Engineering
- Fundamental Research Funds for the Central Universities
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The regioselective difluoromethane sulfonylation or triflylation of resorufin derivatives provides access to 2-difluoromethane sulfonylated or triflylated resorufin derivatives in good yields. The addition of a difluoromethane sulfonyl group enhances the solubility of the chromophore and expands its Stokes shift, allowing for improved imaging of enzyme activity in live cells using a difluoromethane sulfonylated resorufin-based fluorogenic probe.
Reported herein is a regioselective difluoromethane sulfonylation or triflylation of resorufin derivatives, which allows easy access to 2-difluoromethane sulfonylated or triflylated resorufin derivatives in good yields. The installation of a difluoromethane sulfonyl group significantly increases the solubility of the chromophore and expands its Stokes shift. A difluoromethane sulfonylated resorufin-based fluorogenic probe proved to be able to image enzyme activity in live cells with a stronger fluorescence signal compared with its resorufin counterpart.
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