Bacterial epoxide hydrolase-catalyzed resolution of a 2,2-disubstituted oxirane : optimization and upscaling

The epoxide hydrolase-catalyzed resolution of (±)-2-methylglycidyl benzyl ether, a versatile chiral building block for the asymmetric synthesis of bioactive compounds, mediated by whole cells of Rhodococcus ruber SM 1789 was accomplished. Among various parameters (such as temperature, buffer type, p...

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Bibliographic Details
Published inBiotechnology letters Vol. 23; no. 3; pp. 169 - 173
Main Authors HELLSTROM, Helena, STEINREIBER, Andreas, MAYER, Sandra F, FABER, Kurt
Format Journal Article
LanguageEnglish
Published Dordrecht Springer 01.02.2001
Springer Nature B.V
Subjects
(c)-2-methylglycidyl benzyl ether
2-methylglycidyl benzyl ether
Bacteria
Bioactive compounds
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Chemical synthesis
epoxide hydrolase
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
oxirane
Rhodococcus ruber
Enantioselectivity
Enzyme
Enzymatic catalysis
Epoxide hydrolase
Optimization
Operating conditions
Hydrolysis
Asymmetric reaction
Ether hydrolases
Bacteria
Hydrolases
Actinomycetes
Ethylene oxide
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Summary:The epoxide hydrolase-catalyzed resolution of (±)-2-methylglycidyl benzyl ether, a versatile chiral building block for the asymmetric synthesis of bioactive compounds, mediated by whole cells of Rhodococcus ruber SM 1789 was accomplished. Among various parameters (such as temperature, buffer type, pH and catalyst/substrate-ratio) an elevated substrate-concentration proved to be particularly sensitive with respect to a significant enhancement of the enantioselectivity.[PUBLICATION ABSTRACT]
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:0141-5492
1573-6776
DOI:10.1023/A:1005636121060