Back to Search Start Over

Enantioselective hydrolysis of racemic naproxen methyl ester by two-step acetone-treated Candida rugosa lipase

Authors :
Eun Gyo Lee
Hye Soon Won
Bong Hyun Chung
Source :
Process Biochemistry. 37:293-298
Publication Year :
2001
Publisher :
Elsevier BV, 2001.

Abstract

An optically pure ( S )-naproxen was produced by two-step acetone-treated Candida rugosa lipase (CRL) through enantioselective hydrolysis of racemic naproxen methyl ester. The two-step acetone-treated CRL was much more enantioselective than the crude CRL towards the hydrolysis of ( R,S )-naproxen methyl ester, yielding an enantiomeric excess (ee p ) of >98% and an enantiomeric ratio ( E ) of >100. In terms of hydrolysis reaction rate and enantioselectivity, the optimal reaction conditions were found to be 37 °C and pH 6.0. The scaled-up production of ( S )-naproxen was performed in a batch reactor containing 200 ml of substrate solution (50 mM MES buffer containing 200 mM ( R,S )-naproxen methyl ester). After 156 h of reaction, 38.4% of the initial ( R,S )-naproxen methyl ester was hydrolyzed, yielding an enantiomeric excess of 98% and an enantiomeric ratio of>100. Finally, ( S )-naproxen was recovered from the reaction mixture with an optical purity of 98% and a recovery yield of 95%.

Details

ISSN :
13595113
Volume :
37
Database :
OpenAIRE
Journal :
Process Biochemistry
Accession number :
edsair.doi...........f5d45f42c87e3c56b898da4303bc166d
Full Text :
https://doi.org/10.1016/s0032-9592(01)00213-8