T. Watabe, K. Akamatsu, K. Kiyonaga
Jul 2, 1971
Citations
0
Influential Citations
34
Citations
Journal
Biochemical and biophysical research communications
Abstract
Summary 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 (1 R , 2 R ) 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.