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

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 rati...

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Bibliographic Details
Published in:Applied biochemistry and biotechnology 2007-04, Vol.141 (1), p.15-26
Main Authors: Takaç, Serpil, Mutlu, Deniz
Format: Article
Language:English
Subjects:
Bacteria
Batch processing
Candida rugosa
Combinatorial Chemistry Techniques - methods
Computer Simulation
Hydrology
Hydrolysis
Models, Chemical
Organic Chemicals - chemistry
Phase Transition
Solvents - chemistry
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Summary: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 enantiomeric 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 eep 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 degrees 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%.
ISSN:0273-2289
1559-0291
DOI:10.1007/s12010-007-9207-3