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Epoxides as Obligatory Intermediates in the Metabolism of Olefins to Glycols

From the ¹ From the Department of Pharmacology, College of Medicine, University of Illinois, Chicago, Illinois 60680

In the presence of rat liver microsomes and NADPH n-1-octene, n-4-octene and 3-ethyl-2-pentene were converted to the glycols with no trace of epoxides. Increased substitution of ethylenic hydrogen atoms by alkyl groups was found to retard the rate of biological oxidation but to enhance that of epoxidation by perbenzoic acid in chloroform. Microsomes without cofactors hydrolyzed the monosubstituted ethylene oxide more rapidly than the di- or trisubstituted derivatives. The relative rates were in the opposite order of those predicted for acid-catalyzed hydrolysis. The epoxides were found capable of inhibiting epoxide hydrolase. Incubation of microsomes and NADPH with 1 mm n-1-octene in the presence of 20 mm 4,5-epoxy-n-octane yielded both 1,2-epoxy-n-octane and n-octane-1,2-diol. However, in the presence of 20 mm 1,2-epoxy-n-octane, 1 mm n-4-octene yielded 4,5-epoxy-n-octane but no n-octane-4,5-diol. The complete replacement of n-octane-4,5-diol by 4,5-epoxy-n-octane in the presence of the inhibitor indicates that the epoxide is an obligatory intermediate in the conversion of n-4-octene to the glycol.

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				K Ota and B. Hammock Cytosolic and microsomal epoxide hydrolases: differential properties in mammalian liver Science, March 28, 1980; 207(4438): 1479 - 1481. [Abstract] [PDF]