Analogs and derivatives of firefly oxyluciferin, the light emitter in firefly bioluminescence.
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.
White
E H
EH
Department of Chemistry, Johns Hopkins University, Baltimore, MD 21218.
Roswell
D F
DF
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
D007211:Indoles; D011719:Pyrazines; C014730:oxyluciferin; D049454:Firefly Luciferin