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A parametric study on biphasic medium conditions for the enantioselective production of naproxen by Candida rugosa lipase

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Abstract

A parametric study to increase the enantioselectivity of Candida rugosa lipase (CRL) toward S-Naproxen production by the hydrolysis of racemic Naproxen methyl ester in an aqueous-organic biphasic batch system was carried out. Effects of organic solvent type, aqueous phase/organic solvent volume ratio, agitation rate, concentrations of the substrate and the enzyme, pH of the aqueous phase, and temperature on the en antiomeric excess for the product (eep), on the enantiomeric ratio (E) and on the conversion (x) were evaluated. Employing isooctane as the solvent resulted in higher eep, E, and x than those obtained in hexane, cyclohexane, and toluene. The higher the volume ratio of aqueous phase/organic solvent employed, the higher the conversion and enantioselectivity achieved. The increase in agitation rate increased the hydrolysis rate. Higher concentration of racemic Naproxen methyl ester than 10 mg/mL decreased both the conversion and enantioselectivity. The increase in crude CRL concentration resulted in enhancement of x, but the decrease of feep and E. Acidic pH led to higher conversion and enantioselectivity than the medium and alkaline pH values. A further increase in temperature to over 45°C decreased the conversion and enantioselectivity. The highest enantiomeric ratio achieved in the S-Naproxen production was E=171.1, with x=49.8% and eep=95.7%.

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Authors and Affiliations

  1. Department of Chemical, Ankara University Faculty of Engineering, Engineering 06100, Tandogan Ankara, Turkey

    Serpil Takaç & Deniz Mutlu

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  1. Serpil Takaç
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  2. Deniz Mutlu
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Correspondence to Serpil Takaç.

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Takaç, S., Mutlu, D. A parametric study on biphasic medium conditions for the enantioselective production of naproxen by Candida rugosa lipase. Appl Biochem Biotechnol 141, 15–26 (2007). https://doi.org/10.1007/s12010-007-9207-3

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  • DOI: https://doi.org/10.1007/s12010-007-9207-3

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