Abstract
The chemo- and enantioselective capabilities of porcine pancreatic lipase (PPL) in tetrahydrofuran, and Candida rugosa lipase (CRL) in diisopropyl ether have been investigated for the acetylation of racemic 2-alkyl/aryl-3-hydroxypropiophenones, which are important precursors in the synthesis of biologically active chromanones and isoflavanones. A highly chemoselective acetylation of primary hydroxy group in preference to phenolic hydroxy group leading to the formation of enantiomerically enriched monoacetates has been observed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetates / chemistry
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Acetylation
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Animals
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Candida / enzymology*
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Catalysis
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Chromans / chemistry
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Chromatography, High Pressure Liquid
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Crystallography, X-Ray
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Hydroxylation
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Hydroxypropiophenone / analogs & derivatives
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Hydroxypropiophenone / chemistry
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Hydroxypropiophenone / metabolism*
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Isoflavones / chemistry
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Lipase / metabolism*
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Magnetic Resonance Spectroscopy
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Models, Chemical
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Molecular Conformation
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Molecular Structure
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Pancreas / enzymology
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Stereoisomerism
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Structure-Activity Relationship
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Substrate Specificity
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Swine
Substances
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3-hydroxy-1-(2-hydroxy-3,4-dimethoxyphenyl)-2-methylpropanone
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Acetates
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Chromans
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Isoflavones
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Hydroxypropiophenone
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Lipase