Synthesis and bioluminescence of difluoroluciferin |
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| Affiliation: | 1. Department of Chemistry, University of California-Riverside, Riverside, CA 92521, USA;2. Department of Bioengineering, University of California-Riverside, Riverside, CA 92521, USA;3. Stem Cell Center, University of California-Riverside, Riverside, CA 92521, USA;1. CNRS, SRSMC, UMR 7565, Vandœuvre-lès-Nancy, F-54506, France;2. Université de Lorraine, SRSMC, UMR 7565, Nancy F-54001, France;3. ABC Platform®, Nancy F-54001, France;1. Division of Chemistry and Materials Science, Graduate School of Engineering, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan;2. Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan;3. Graduate School of Science and Technology, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan;1. Centro de Desenvolvimento da Tecnologia Nuclear – CDTN. Campus da UFMG, Av. Pres. Antônio Carlos, 6627 - Pampulha, Belo Horizonte, MG 31270-901, Brazil;2. Universidade Federal de Minas Gerais, Departamento de Engenharia Nuclear, Escola de Engenharia, Universidade Federal de Minas Gerais - UFMG, Avenida Antônio Carlos, 6627, Pampulha, Belo Horizonte, MG 31270-901, Brazil;1. Department of Anatomy and Cell Biology, University of Florida, Gainesville, FL 32610, USA;2. Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA;3. Research Institute for Solar and Sustainable Energies (RISE), School of Materials Science & Engineering, Gwangju Institute of Science and Technology, 123 Cheomdan-gwagiro, Buk-gu, Gwangju 500-712, Republic of Korea;1. Department of Biophysics and Free Radical Research Center, Medical College of Wisconsin, Milwaukee, WI 53226, United States;2. Institute of Polymer and Dye Technology, Faculty of Chemistry, Lodz University of Technology, Stefanowskiego 12/16, 90-924 Lodz, Poland;3. Aix-Marseille Université, CNRS, ICR UMR 7273, 13397 Marseille, France |
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| Abstract: | A new synthesis route to firefly luciferin analogs was developed via the synthesis of 5′,7′-difluoroluciferin. As a luciferase substrate, it produces maximal bioluminescence at a much lower pH than is optimal for native luciferin, and at lower pH it gives much more of the red-shifted emission that is characteristic of the phenolate. These features are attributed to the enhanced acidity of the o,o-difluorophenol. |
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| Keywords: | pH dependence Firefly luciferase Luminescence Substituent effect Fluorination |
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