Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources

The enantioselectivity (E) of native lipases from Aspergillus niger, Aspergillus terreus, Fusarium oxysporum, Mucor javanicus, Penicillium solitum and Rhizopus javanicus in the resolution of (R,S)-ibuprofen and (R,S)-ketoprofenenantiomers by esterification reaction with 1-propanol in isooctane was compared with known commercial Candida rugosa (Sigma) and Candida antarctica (Novozym®435) lipases. In the resolution of (R,S)-ibuprofen, C. rugosa lipase showed good selectivity (E = 12) while Novozym®435 (E = 6.7) and A. niger (E = 4.8) lipases had intermediate selectivities. Other enzymes were much less selective (E around 2.3 and 1.5), under tested conditions. After preliminary optimization of reaction conditions (water content, enzyme concentration and presence of additives) the enantioselectivity of native A. niger lipase could be enhanced substantially (E = 15). All tested lipases showed low selectivity in the resolution of (R,S)-ketoprofen because poor ester yields and low enantiomeric excess of the acid remaining were achieved.

Bibliographic Details

Main Authors:	Carvalho,Patrícia de Oliveira, Contesini,Fabiano Jares, Ikegaki,Masaharu
Format:	Digital revista
Language:	English
Published:	Sociedade Brasileira de Microbiologia 2006
Online Access:	http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822006000300024
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