Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources
Autor(a) principal: | |
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Data de Publicação: | 2006 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Brazilian Journal of Microbiology |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822006000300024 |
Resumo: | 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. |
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Brazilian Journal of Microbiology |
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Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sourceslipase(R,S)-ibuprofen(R,S)-ketoprofenenantioselectivityThe 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.Sociedade Brasileira de Microbiologia2006-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822006000300024Brazilian Journal of Microbiology v.37 n.3 2006reponame:Brazilian Journal of Microbiologyinstname:Sociedade Brasileira de Microbiologia (SBM)instacron:SBM10.1590/S1517-83822006000300024info:eu-repo/semantics/openAccessCarvalho,Patrícia de OliveiraContesini,Fabiano JaresIkegaki,Masaharueng2006-12-18T00:00:00Zoai:scielo:S1517-83822006000300024Revistahttps://www.scielo.br/j/bjm/ONGhttps://old.scielo.br/oai/scielo-oai.phpbjm@sbmicrobiologia.org.br||mbmartin@usp.br1678-44051517-8382opendoar:2006-12-18T00:00Brazilian Journal of Microbiology - Sociedade Brasileira de Microbiologia (SBM)false |
dc.title.none.fl_str_mv |
Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources |
title |
Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources |
spellingShingle |
Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources Carvalho,Patrícia de Oliveira lipase (R,S)-ibuprofen (R,S)-ketoprofen enantioselectivity |
title_short |
Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources |
title_full |
Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources |
title_fullStr |
Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources |
title_full_unstemmed |
Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources |
title_sort |
Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources |
author |
Carvalho,Patrícia de Oliveira |
author_facet |
Carvalho,Patrícia de Oliveira Contesini,Fabiano Jares Ikegaki,Masaharu |
author_role |
author |
author2 |
Contesini,Fabiano Jares Ikegaki,Masaharu |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Carvalho,Patrícia de Oliveira Contesini,Fabiano Jares Ikegaki,Masaharu |
dc.subject.por.fl_str_mv |
lipase (R,S)-ibuprofen (R,S)-ketoprofen enantioselectivity |
topic |
lipase (R,S)-ibuprofen (R,S)-ketoprofen enantioselectivity |
description |
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. |
publishDate |
2006 |
dc.date.none.fl_str_mv |
2006-09-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822006000300024 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822006000300024 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S1517-83822006000300024 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Microbiologia |
publisher.none.fl_str_mv |
Sociedade Brasileira de Microbiologia |
dc.source.none.fl_str_mv |
Brazilian Journal of Microbiology v.37 n.3 2006 reponame:Brazilian Journal of Microbiology instname:Sociedade Brasileira de Microbiologia (SBM) instacron:SBM |
instname_str |
Sociedade Brasileira de Microbiologia (SBM) |
instacron_str |
SBM |
institution |
SBM |
reponame_str |
Brazilian Journal of Microbiology |
collection |
Brazilian Journal of Microbiology |
repository.name.fl_str_mv |
Brazilian Journal of Microbiology - Sociedade Brasileira de Microbiologia (SBM) |
repository.mail.fl_str_mv |
bjm@sbmicrobiologia.org.br||mbmartin@usp.br |
_version_ |
1752122200628920320 |