STEREOSELECTIVITY OF IN-VITRO ISOPRENE METABOLISM

被引：26

作者：

WISTUBA, D ^{[1
]}

WEIGAND, K ^{[1
]}

PETER, H ^{[1
]}

机构：

[1] UNIV DORTMUND,INST ARBEITSPHYSIOL,D-44139 DORTMUND,GERMANY

来源：

CHEMICAL RESEARCH IN TOXICOLOGY | 1994年 / 7卷 / 03期

关键词：

D O I：

10.1021/tx00039a010

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The stereoselectivity of the in vitro conversion of isoprene by liver enzymes of rats ana mice was determined. Isoprene was epoxidized by cytochrome P450 of rats and mice to 2-isopropenyioxirane and 2-methyl-2-vinyloxirane with slight but different product enantioselectivity. Only with mouse liver microsomes was a distinct regioselectivity observed. Both monooxiranes were further epoxidized to 2-methyl-2,2'-bioxirane with substrate enantioselectivity, product diastereoselectivity, and with product enantioselectivity. The epoxide hydrolase-catalyzed hydrolysis with rat and mouse liver microsomes occurs with substrate enantioselectivity. A better kinetic resolution was found for 2-isopropenyloxirane than for 2-methyl-2-vinyloxirane. While 2(R)-isopropenyloxirane was conjugated preferentially with glutathione, catalyzed by glutathione S-transferase, no enantiomer differentiation takes place in the case of 2-methyl-2-vinyloxirane.

引用

页码：336 / 343

页数：8

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