title: Synthesis and bioluminescence of difluoroluciferin.
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.
authors.affiliation: Department of Chemistry, University of California-Riverside, Riverside, CA 92521, USA; Stem Cell Center, University of California-Riverside, Riverside, CA 92521, USA. Electronic address: michael.pirrung@ucr.edu.
authors.forename: Michael C
authors.initials: MC
authors.lastname: Pirrung
authors.affiliation: Department of Chemistry, University of California-Riverside, Riverside, CA 92521, USA.
authors.forename: Goutam
authors.initials: G
authors.lastname: Biswas
authors.affiliation: Department of Bioengineering, University of California-Riverside, Riverside, CA 92521, USA.
authors.forename: Natalie
authors.initials: N
authors.lastname: De Howitt
authors.affiliation: Department of Bioengineering, University of California-Riverside, Riverside, CA 92521, USA; Stem Cell Center, University of California-Riverside, Riverside, CA 92521, USA.
authors.forename: Jiayu
authors.initials: J
authors.lastname: Liao
mesh_terms: D049454:Firefly Luciferin / Q000031:analogs & derivatives* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D049449:Luminescence; D008163:Luminescent Measurements; D015394:Molecular Structure
chemical_list: C000596386:5',7'-difluoroluciferin; D049454:Firefly Luciferin
keywords: Firefly luciferase; Fluorination; Luminescence; Substituent effect; pH dependence