A chemo-enzymatic route for the preparation of chiral (S)-3-hydroxy-3-phenylpropanoic acid

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 °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 β-hydroxy acid by PPL.

Keywords

Optically active β-hydroxy acid / Porcine pancreas lipase(PPL) / Chemo-enzymatic process

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