title: Analogs and derivatives of firefly oxyluciferin, the light emitter in firefly bioluminescence.
abstract: The 5-methyl analog of firefly oxyluciferin, two isomeric O-methyl ether derivatives of it and an O,O'-dimethyl ether derivative were synthesized and their UV absorption and fluorescence emission spectra were determined. Comparisons of the emission data with the emission wavelength in bioluminescence indicate that the mono-anions of firefly oxyluciferin are candidates for the light-emitters in bioluminescence. Further, we have found that the chemiluminescence of active esters of firefly luciferin produces (from the keto form of oxyluciferin) only red light emission under a variety of conditions; a yellow-green light emission (from the enolic forms of the oxyluciferin product) could not be elicited.
authors.affiliation: Department of Chemistry, Johns Hopkins University, Baltimore, MD 21218.
authors.forename: E H
authors.initials: EH
authors.lastname: White
authors.forename: D F
authors.initials: DF
authors.lastname: Roswell
mesh_terms: D000818:Animals; D001517:Coleoptera / Q000502:physiology*; D049454:Firefly Luciferin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles; D049449:Luminescence; D011719:Pyrazines; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry; D013329:Structure-Activity Relationship
chemical_list: D007211:Indoles; D011719:Pyrazines; C014730:oxyluciferin; D049454:Firefly Luciferin