Enantioselective resolution of racemic ibuprofen esters using different lipases immobilized on octyl sepharose

• Published in: Journal of molecular catalysis. B, Enzymatic Vol. 104; pp. 87 - 94
• Main Authors: Yousefi, Maryam, Mohammadi, Mehdi, Habibi, Zohreh
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 01.06.2014; Elsevier
• Subjects: (R,S)-ibuprofen; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Candida rugosa lipase; Fundamental and applied biological sciences. Psychology; Immobilization; Kinetic resolution; Methods. Procedures. Technologies; Rhizopus oryzae lipase; Immobilization; (R,S)-ibuprofen; Rhizopus oryzae lipase; Kinetic resolution; Candida rugosa lipase; Yeast; Zygomycota; Separation; Enantioselectivity; Enzyme; Triacylglycerol lipase; Esterases; Carboxylic ester hydrolases; Fungi; Ester; Racemic; Rhizopus oryzae; Enantiomer; Ibuprofen; Hydrolases; Fungi Imperfecti; Candida rugosa
• ISSN: 1381-1177; 1873-3158
• DOI: 10.1016/j.molcatb.2014.03.005

•Candida rugosa lipase (CRL) and Rhizopus oryzae lipase (ROL) were immobilized on octyl-sepharose.•The immobilized preparations catalyzed hydrolysis of racemic ibuprofen esters.•Hydrolysis of racemic ibuprofen esters by CRL resulted in higher enantioselectivities than ROL (ee>95%). Here we report the stereoselective hydrolysis of racemic esters catalyzed by Candida rugosa lipase (CRL) and Rhizopus oryzae lipase (ROL) immobilized on octyl-sepharose via physical adsorption. Hydrophobic immobilization caused to almost six fold hyperactivation with 229.2 and 81.3U/mg enzyme for immobilized CRL and ROL, respectively (13.2 and 48.75U/mg for corresponding free enzyme). Based on the preliminary results, CRL was chosen for further investigation. The performance and yield of the reaction were evaluated as a function of the critical reaction parameters such as temperature, enzyme to substrate ratio and organic co-solvent. An increase in the temperature resulted to decrease in enantioselectivity of hydrolysis reaction. The hydrolysis reactions were carried out in presence of two organic solvents; n-hexane and isooctane. Generally n-hexane was a better co-solvent compared to isooctane. High enantioselective hydrolysis of the racemic esters (yielding S(+) ibuprofen; ee≥95%) can be achieved using the immobilized CRL. Among various esters the kinetic resolution of ibuprofen butyl ester yielded the best results (E value 70 and 74; conversion 14.6 and 8.9 in n-hexane and isooctane, respectively). The immobilized derivatives were re-used in four cycles and showed little decrease in enantiomeric excess of (S)-ibuprofen. 96.7eep and conversion 14.6 in first cycle reached to 90.5eep and conversion 11.3 in the forth cycle.