Enzymatic Synthesis of both Enantiomers of Ethyl 4-Cyano-3-Hydroxybutanoate

Jian Zhong Jin; Jie Zhang

doi:10.4028/www.scientific.net/AMR.343-344.448

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Emulsifier’s Influence on the Quality of Frozen Dough
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Determination and Microbial Degradation of Lambda-Cyhalothrin
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Molecular Cloning and Tissue-Specific Expression of the Heart-Type Fatty Acid-Binding Protein (H-FABP)
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Enzymatic Synthesis of both Enantiomers of Ethyl 4-Cyano-3-Hydroxybutanoate
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Highly Enantioselective Hydrolysis of Racemic Isopropyl Tert-Leucinate by Newly Discovered Baclicus Lincheniformis Jx010 for Synthesis of L-Tert-Butyl Leucine
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Antioxidant Activities of Extracts from Pholiota Nameko
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Antioxidant Properties of Hot Water Extracts from Armillaria Mellea and Hohenbuehelia Serotina
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Ionizing Irradiation Property of L(+)-Alpha-Phenylglycine in Acid Aqueous Solution
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Enzymatic Synthesis of both Enantiomers of Ethyl 4-Cyano-3-Hydroxybutanoate

Abstract:

(R)-Ethyl 4-cyano-3-hydroxybutanoate is the key intermediate for the synthesis of liptor used for lowering high cholesterol and triglycerides. Firstly both enantiomers of ethyl 4-cyano-3-hydroxybu- tanoate were prepared by the enzymatic reduction of ethyl 4-cyano-3-oxobutanoate with two whole cells in high ee and high yield. The (R)-enantiomer was obtained in 89.8% yield and 98.5% ee in the catalysis of 20 mM substrate by the strain Bacillus pumilus Phe-C3; the (S)-enantiomer was achieved in 83.1% yield and 95.4% ee in the catalysis of 10 mM substrate by the strain Klebsiella pneumomiae Phe-E4. Preparative synthesis were carried out on 200-L scale.