A Chemo-enzymatic Route for the Preparation of Chiral (S)-3-Hydroxy-3-phenylpropanoic Acid

作者：Zhao Ying; Ma Haiping; Fu Zhijing; Zhang Guoyan^*

来源：Chemical Research in Chinese Universities, 2014, 30(6): 915-918.

DOI：10.1007/s40242-014-4300-y

• Optically active beta-hydroxy acid
• Porcine pancreas lipase(PPL)
• Chemo-enzymatic process

(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 degrees C 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 beta-hydroxy acid by PPL.

• 出版日期2014-12
• 单位吉林大学