Biological Activity
The in vivo synthesis of firefly luciferin is not completely understood. Only the final step of the enzymatic pathway has been studied, which is the condensation reaction of -cysteine with 2-cyano-6-hydroxybenzothiazole, and is the same reaction used to produce the compound synthetically. This was confirmed by radiolabeling of atoms in the two compounds and by identification of a luciferin-regenerating enzyme.
In firefly, oxidation of luciferins, which is catalyzed by luciferases, yields a peroxy compound 1,2-dioxetane. The dioxetane is unstable and decays spontaneously to carbon dioxide and excited ketones, which release excess energy by emitting light (bioluminescence).
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