The chemiluminescence of amides and monoacyl hydrazides based on firefly dehydroluciferin.
Monoacyl hydrazides based on 5-methyldehydroluciferin and simpler analogs have been synthesized; they proved to be chemiluminescent on treatment with a strong base in DMSO in the presence of oxygen. The light emitters in these cases appear to be the corresponding carboxylate ions; a pathway involving an oxidative decarboxylation was eliminated as a possibility by consideration of the fluorescence wavelengths of the corresponding oxyluciferins. A reaction mechanism for the luminescence involving the possible intermediacy of an azadioxetane is proposed. The corresponding amides were also synthesized; they proved to be equally chemiluminescent to the hydrazides in the dehydroluciferin series.
White
E H
EH
Department of Chemistry, Johns Hopkins University, Baltimore, MD 21218.
Li
M
M
Roswell
D F
DF
D000215:Acylation; D000577:Amides / Q000737:chemistry*; D000818:Animals; D001517:Coleoptera; D049454:Firefly Luciferin / Q000031:analogs & derivatives*; D006834:Hydrazines / Q000737:chemistry*; D049449:Luminescence; D013329:Structure-Activity Relationship
D000577:Amides; D006834:Hydrazines; D049454:Firefly Luciferin