Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp HXN-200: simple syntheses of alicyclic vicinal trans-diols

Hydrolysis of N-benzyloxycarbonyl-3,4-epoxy-pyrrolidine and cyclohexene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200, respectively, gave the corresponding vicinal trans-diols in high ee and yield, representing the first example of enantioselective hydrolysis of a meso-epoxide with a...

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Published inChemical communications (Cambridge, England) no. 8; pp. 960 - 961
Main Authors Chang, DL, Wang, ZS, Heringa, MF, Wirthner, R, Witholt, B, Li, Z
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.04.2003
Subjects
Alcohols - chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Cyclohexanes - chemistry
Cyclohexenes
Epoxide Hydrolases - chemistry
Epoxy Compounds - chemistry
Hydrocarbons, Alicyclic - chemistry
Hydrolysis
Physical Sciences
Pyrrolidines - chemistry
Science & Technology
Sphingomonas - enzymology
Stereoisomerism
MICROBIOLOGICAL TRANSFORMATIONS
KINETIC RESOLUTION
HYDROXYLATION
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Summary:Hydrolysis of N-benzyloxycarbonyl-3,4-epoxy-pyrrolidine and cyclohexene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200, respectively, gave the corresponding vicinal trans-diols in high ee and yield, representing the first example of enantioselective hydrolysis of a meso-epoxide with a bacterial epoxide hydrolase.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/b300435j