Epoxides as obligatory intermediates in the metabolism of olefins to glycols.

Abstract 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.

• Publication year

  1970

• Venue

  Journal of Biological Chemistry

• Publication date

  1970-10-25

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1016/s0021-9258(18)62746-2PMID 4394227
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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