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

Authors
Chiappe, C De Rubertis, A Marioni, F Simonetti, A
Citation
C. Chiappe et al., 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, J MOL CAT B, 10(5), 2000, pp. 539-544
Citations number
28
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
ISSN journal
13811177 → ACNP
Volume
10
Issue
5
Year of publication
2000
Pages
539 - 544
Database
ISI
SICI code
1381-1177(20001002)10:5<539:TACOTM>2.0.ZU;2-U
Abstract
The enzymatic hydrolysis of exo-2,3-epoxy-norbornane (1) with a crude rabbi t liver microsomal preparation occurred with a rearrangement and gave selec tively (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 s ame 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 ob served products is proposed. (C) 2000 Elsevier Science B.V. All rights rese rved.