Enantioselective hydrolysis of epoxides: the employment of the soluble fraction from Vicia sativa seedlings

Biocatalytic hydrolysis of meso and racemic aryl- and alkyl-oxiranes was accomplished by employing the epoxide hydrolase activity of the soluble fraction of Vicia sativa seedlings. Whereas meso epoxides were not hydrolyzed by this fraction, racemic compounds were transformed into the corresponding d...

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Bibliographic Details
Published inJournal of molecular catalysis. B, Enzymatic Vol. 14; no. 4; pp. 125 - 129
Main Authors Chiappe, Cinzia, De Rubertis, Antonietta, Marioni, Franco, Pelagotti, Filippo
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier B.V 06.07.2001
Elsevier Science
Subjects
Asymmetric hydrolysis
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Epoxide hydrolase
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Plant
Epoxide hydrolase
Plant
Asymmetric hydrolysis
Enantioselectivity
Enzyme
Enzymatic catalysis
Hydrolysis
Vicia sativa
Leguminosae
Dicotyledones
Biotransformation
Angiospermae
Epoxide
Ether hydrolases
Hydrolases
Spermatophyta
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Summary:Biocatalytic hydrolysis of meso and racemic aryl- and alkyl-oxiranes was accomplished by employing the epoxide hydrolase activity of the soluble fraction of Vicia sativa seedlings. Whereas meso epoxides were not hydrolyzed by this fraction, racemic compounds were transformed into the corresponding diols by formal anti-stereoselective water attack. Both substrate and product enantioselectivity were strongly influenced by the chains length and the presence of a hydroxyl group.
ISSN:1381-1177
1873-3158
DOI:10.1016/S1381-1177(00)00245-9