Stereochemical course of the biotransformation of isoprene monoepoxides and of the corresponding diols with liver microsomes from control and induced rats

C Chiappe, A De Rubertis, V Tinagli…

Index: Chiappe; De Rubertis; Tinagli; Amato; Gervasi Chemical Research in Toxicology, 2000 , vol. 13, # 9 p. 831 - 838

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Citation Number: 18

Abstract

The stereochemical course of the biotransformation of isoprene by liver enzymes from control and induced rats has been determined. Between the two primarily formed metabolites, 2-methyl-2-vinyloxirane (2) and isopropenyloxirane (3), epoxide 2 is rapidly transformed into the corresponding vicinal racemic diol 4, predominantly through a nonenzymatic hydrolysis reaction. At variance, epoxide 3 is mainly biotransformed into the ...