Abstract
Stereochemistry in the hydrolysis of isomeric cis- and trans-olefin oxides by hepatic microsomal epoxide hydrolase has been described. cis- and trans-Stilbene oxides used as model substrates for this purpose were hydrolyzed with a strict stereos electivity by rabbit liver microsomes to d-threo- and meso-1, 2-diphenyl-1, 2-ethanediols, respectively. The previously established absolute configuration of the d-threo-glycol (1R, 2R) indicates it to be formed, in the enzymatic reaction process, as a result of the selective attack of a hydroxyl anion on only one oxiran carbon of the symmetric cis-olefin oxide. The rate of the enzymatic glycol formation reaction is much higher in cis-stilbene oxide than in the trans-isomer.
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