| A Chemo-enzymatic Route for the Preparation of Chiral （S）-3-Hydroxy-3-phenylpropanoic Acid |
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| 引用本文： | ZHAO Ying MA Haiping FU Zhijing ZHANG Guoyan. A Chemo-enzymatic Route for the Preparation of Chiral （S）-3-Hydroxy-3-phenylpropanoic Acid[J]. 高等学校化学研究, 2014, 30(6): 915-918. DOI: 10.1007/s40242-014-4300-y |
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| 作者姓名： | ZHAO Ying MA Haiping FU Zhijing ZHANG Guoyan |
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| 作者单位： | College of Chemistry, Jilin University, Changchun 130012, P. R. China |
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| 基金项目： | Supported by the Graduate Training Program Foundation of Jilin University, China. The authors gratefully acknowledge Prof. ZHENG Liang- yu（Key Laboratory for Molecular Enzymology and Enginee- ring of Ministry of Education of China） for her instructive suggestions |
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| 摘 要： | （S）-3-Hydroxy-3-phenylpropanoic acid is a potential progenitor of optically pure tomoxetine hydrochlo- ride and fluoxetine hydrochloride which are currently available antidepressant drugs. We report here the chemical synthesis of racemic substrate （R,S）-ethyl 3-hydroxy-3-phenylpropanoate and enzymatic preparation of S-isomer of the substrate by employing Porcine pancreas lipase（PPL） as a biocatalyst. Optimum enzyme-catalyzed reaction con- ditions, such as the effects of the temperature, pH and solvents on conversion degree and enantiomeric excess, were studied. An optimal temperature of 35 ℃ and pH=7.5 are the best for the resolution of （R,S）-ethyl 3-hydroxy-3- pheylpropanoate by PPL when 0.1 mol/L phosphate buffer solution acts as a medium. This work provides a practi- cally chemo-enzvmatic oreoaration of chiral β-hvdroxv acid by PPL.
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| 关 键 词： | 化学合成 羟基 苯基 丙酸 手性 路线 酶法 磷酸盐缓冲液 |
| 收稿时间： | 2014-08-07 |
A Chemo-enzymatic Route for the Preparation of Chiral (S)-3-Hydroxy-3-phenylpropanoic Acid |
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| ZHAO Ying,MA Haiping,FU Zhijing,ZHANG Guoyan. A Chemo-enzymatic Route for the Preparation of Chiral (S)-3-Hydroxy-3-phenylpropanoic Acid[J]. Chemical Research in Chinese University, 2014, 30(6): 915-918. DOI: 10.1007/s40242-014-4300-y |
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| Authors: | ZHAO Ying MA Haiping FU Zhijing ZHANG Guoyan |
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| Affiliation: | College of Chemistry, Jilin University, Changchun 130012, P. R. China |
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| Abstract: | (S)-3-Hydroxy-3-phenylpropanoic acid is a potential progenitor of optically pure tomoxetine hydrochloride and fluoxetine hydrochloride which are currently available antidepressant drugs. We report here the chemical synthesis of racemic substrate (R,S)-ethyl 3-hydroxy-3-phenylpropanoate and enzymatic preparation of S-isomer of the substrate by employing Porcine pancreas lipase(PPL) as a biocatalyst. Optimum enzyme-catalyzed reaction conditions, such as the effects of the temperature, pH and solvents on conversion degree and enantiomeric excess, were studied. An optimal temperature of 35 ℃ and pH=7.5 are the best for the resolution of (R,S)-ethyl 3-hydroxy-3- pheylpropanoate by PPL when 0.1 mol/L phosphate buffer solution acts as a medium. This work provides a practically chemo-enzymatic preparation of chiral β-hydroxy acid by PPL. |
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| Keywords: | Optically active β-hydroxy acid Porcine pancreas lipase(PPL) Chemo-enzymatic process |
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