Cumene hydroperoxide effected hydroperoxidation by cytochrome P-450.
9-Methylfluorene was found to be oxygenated to 9-hydroperoxy-9-methylfluorene and 9-hydroxy-9-methylfluorene by cytochrome P-450 in the presence of cumene hydroperoxide. Molecular oxygen is required and carbon monoxide is inhibitory. The reaction is inhibited by SKF-525A and metyrapone. Metyrapone and cumene hydroperoxide also retard the conversion of 9-hydroperoxy-9-methylfluorene to 9-hydroxy-9-methylfluorene. The reaction is different from hydroperoxide-supported oxygenation, since the cumene hydroperoxide appears to act as an effector of the enzyme rather than oxygen donor. It is suggested that substrates with stable radicals can be dioxygenated in this manner.
D000818:Animals; D001555:Benzene Derivatives / Q000494:pharmacology*; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D005449:Fluorenes / Q000378:metabolism; D008297:Male; D008797:Metyrapone / Q000494:pharmacology; D008862:Microsomes, Liver / Q000201:enzymology*; D010084:Oxidation-Reduction; D051381:Rats
D001555:Benzene Derivatives; D005449:Fluorenes; C044948:9-hydroperoxy-9-methylfluorene; C044947:9-hydroxy-9-methylfluorene; D003577:Cytochrome P-450 Enzyme System; C030636:9-methylfluorene; C007164:cumene hydroperoxide; D008797:Metyrapone