Abstract
The use of a fully active, synthetic analogue of coelenterate-type luciferin labeled in the carbonyl position with 14C and 18O was used to probe the mechanism of the Renilla luciferase catalyzed oxidative decarboxylation of this compound. In the presence of 17O 2, the CO 2 produced in this oxidation can be shown to contain approximately one 17O atom per CO 2 molecule. This result is consistent with a cyclic peroxide or dioxetanone-type mechanism. In the presence of luciferase, the oxygen in the luciferin carbonyl group is rapidly exchanged with solvent water prior to the production of CO 2. Thus, the reaction CO 2 contains considerable oxygen derived from water, via exchange with the carbonyl group, and about one oxygen from O 2 via a cyclic peroxide.
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