Optimization of lipase-catalyzed enantioselective production of 1-phenyl 1-propanol using response surface methodology.
Optically active 1-phenyl 1-propanol is used as a chiral building block and synthetic intermediate in the pharmaceutical industries. In this study, the enantioselective production of 1-phenyl 1-propanol was investigated systematically using response surface methodology (RSM). Before RSM was applied, the effects of the enzyme source, the type of acyl donor, and the type of solvent on the kinetic resolution of 1-phenyl 1-propanol were studied. The best results were obtained with Candida antartica lipase (commercially available as Novozym 435), vinyl laurate as the acyl donor, and isooctane as the solvent. In the RSM, substrate concentration, molar ratio of acyl donor to the substrate, amount of enzyme, temperature, and stirring rate were chosen as independent variables. The predicted optimum conditions for a higher enantiomeric excess (ee) were as follows: substrate concentration, 233 mM; molar ratio of acyl donor to substrate, 1.5; enzyme amount, 116 mg; temperature, 47 °C; and stirring rate, 161 rpm. A verification experiment conducted at these optimized conditions for maximum ee yielded 91% for 3 hr, which is higher than the predicted value of 83%. The effect of microwave on the ee was also investigated and ee reached 87% at only 5 min.
Faculty of Engineering, Department of Chemical Engineering, Ankara University, Ankara, Turkey.
Asli
A
Soyer
Emine
E
Bayraktar
Ulku
U
Mehmetoglu
D001426:Bacterial Proteins / Q000378:metabolism*; D002175:Candida / Q000201:enzymology; D004800:Enzymes, Immobilized; D005656:Fungal Proteins / Q000378:metabolism*; D007218:Industrial Microbiology / Q000379:methods*; D008049:Lipase / Q000378:metabolism*; D009089:Mucor / Q000201:enzymology; D020005:Propanols / Q000378:metabolism*; D011549:Pseudomonas / Q000201:enzymology; D020103:Rhizomucor / Q000201:enzymology; D012997:Solvents; D013237:Stereoisomerism
D001426:Bacterial Proteins; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D020005:Propanols; D012997:Solvents; C439395:1-phenylpropanol; C093667:Novozyme 435; D008049:Lipase