The anomalous course of the microsomal transformation of the exo-2,3-epoxides of norbornene and norbornadiene.: The possible involvement of a general acid activation during the enzymatic hydrolysis of these oxides

被引：8

作者：

Chiappe, C ^{[1
]}

De Rubertis, A ^{[1
]}

Marioni, F ^{[1
]}

Simonetti, A ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2000年 / 10卷 / 05期

关键词：

microsomal biotransformation; mEH; reaction mechanism;

D O I：

10.1016/S1381-1177(00)00097-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The enzymatic hydrolysis of exo-2,3-epoxy-norbornane (1) with a crude rabbit liver microsomal preparation occurred with a rearrangement and gave selectively (2 R,7S)-bicyclo[2.2.1]heptane-2,7-diol (3), enantiomeric excess (ee) 30 +/- 2%. The analogous exo-2,3-epoxy-5-norbornene (2) gave, under the same conditions, exclusively endo-6-hydroxymethylbicyclo-[3.1.0]hex-2-ene (4), arising from the microsomal catalyzed reduction of the first formed endo-6-formylbicyclo-[3.1.0]hex-2-ene (5). A mechanistic explanation for the observed products is proposed. (C) 2000 Elsevier Science B.V. All rights reserved.

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页码：539 / 544

页数：6

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