Kinetics of Enantioselective Esterification of Naproxen by Lipase in Organic Solvents

The kinetics of stereoselective esterification of racemic Naproxen with trimethylsilyl methanol by Candida cylindracea lipase in organic solvents has been investigated. A Ping-Pong Bi Bi mechanism with competitive inhibition by this alcohol for each enantiomer -has been identified. The rate equations were further analyzed in the time-course reaction after considering the effect of enzyme deactivation in the organic mixtures, but not in isooctane. Effects of the hydrophobicity of solvent on the solubility of the racemate, the kinetic parameters and their combinations are also discussed.

[1]  S. Tsai,et al.  Effect of solvent on enantioselective esterification of naproxen by lipase with trimethylsilyl methanol , 1994, Biotechnology and bioengineering.

[2]  M. Reuss,et al.  A kinetic study of immobilized lipase catalysing the synthesis of isoamyl acetate by transesterification in n-hexane. , 1992, Enzyme and microbial technology.

[3]  D. Combes,et al.  Kinetics of geranyl acetate synthesis by lipase-catalysed transesterification in n-hexane , 1992 .

[4]  H. R. Sonawane,et al.  Recent developments in the synthesis of optically active α-arylpropanoic acids: An important class of non-steroidal anti-inflammatory agents☆ , 1992 .

[5]  K. Hult,et al.  Alcohol Induced Reversal of Enantioselectivity in a Lipase Catalyzed Resolution of 2-Chloropropionic Acid , 1992 .

[6]  P. Halling,et al.  Solvent effects on biocatalysis in organic systems: Equilibrium position and rates of lipase catalyzed esterification , 1991, Biotechnology and bioengineering.

[7]  D. Bianchi,et al.  Enzymatic resolution of (S)‐(+)‐naproxen in a continuous reactor , 1991, Biotechnology and bioengineering.

[8]  J. Dordick,et al.  Substrate structure and solvent hydrophobicity control lipase catalysis and enantioselectivity in organic media , 1991 .

[9]  J. Prausnitz,et al.  Kinetics of lipase-catalysed interesterification of triglycerides in cyclohexane , 1991 .

[10]  K. Engel.  Lipase-catalyzed enantioselective esterification of 2-methylalkanoic acids , 1991 .

[11]  R. Willemot,et al.  Kinetic study of esterification by immobilized lipase in n‐hexane , 1990, FEBS letters.

[12]  M. J. Barton,et al.  Enzymatic resolution of (R,S)-2-(4-hydroxyphenoxy) propionic acid , 1990 .

[13]  A. Klibanov.  Asymmetric transformations catalyzed by enzymes in organic solvents , 1990 .

[14]  Ching-Shih Chen,et al.  General Aspects and Optimization of Enantioselective Biocatalysis in Organic Solvents: The Use of Lipases [New Synthetic Methods (76)] , 1989 .

[15]  Shih-Hsiung Wu,et al.  The use of microbial enzymes for the synthesis of optically active pharmaceuticals , 1988 .

[16]  C. Laane,et al.  Rules for optimization of biocatalysis in organic solvents , 1987, Biotechnology and bioengineering.

[17]  C. Sih,et al.  A facile enzymatic resolution process for the preparation of (+)-S-2-(6-methoxy-2-naphthyl)propionic acid (naproxen) , 1986 .

[18]  A. Klibanov,et al.  Resolution of racemic mixtures via lipase catalysis in organic solvents , 1985 .

[19]  Alexander M. Klibanov,et al.  Enzyme-catalyzed processes in organic solvents. , 1985 .