Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects

Autores
Foresti, María Laura; Galle, Marianela Edith; Ferreira, Maria Lujan; Briand, Laura Estefania
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the last years enantioselective esterification of racemic ibuprofen performed in organic solvent media and catalyzed by lipases has been proposed as an effective way to increase the concentration of unesterified S-ibuprofen in the racemic mixture. In this contribution, a system free of organic solvent is proposed as a novel eco-friendly medium to perform the enantioselective enzymatic esterification of (R,S)-ibuprofen. Results showed that the reaction in excess of the esterifying alcohol in a system free of organic solvent is possible if the proper conditions are set. The effects of the amount of water present in the reaction medium, the volume of the alcohol used as acyl acceptor, the enzyme loading, and the reaction temperature, were alternatively analyzed in terms of the (conversion of ibuprofen towards the ester) reaction yield and enantiomeric excess achieved. Alcohol concentration showed to be determinant for both biocatalyst activity and enantioselectivity. The initial water content of reaction medium also showed to be a key parameter in a compromise between biocatalyst hydration and ester hydrolysis. By using 1 ml of ethanol as esterifying reagent, with an initial optimal water content of 4.8% v/v, at 45 °C, and with 160 mg of Novozym a total conversion of 62% and an enantiomeric excess of substrate of 54% were obtained in 72 hours of reaction.
Fil: Foresti, María Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología En Polimeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología En Polimeros y Nanotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahia Blanca. Planta Piloto de Ingeniería Química (I). Grupo Vinculado al Plapiqui - Investigación y Desarrollo en Tecnología Química; Argentina
Fil: Galle, Marianela Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Ferreira, Maria Lujan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Briand, Laura Estefania. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Materia
Ibuprofeno
Lipase
Enantioselective
Esterification
Molecular Modeling
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/22921
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/22921
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspectsForesti, María LauraGalle, Marianela EdithFerreira, Maria LujanBriand, Laura EstefaniaIbuprofenoLipaseEnantioselectiveEsterificationMolecular Modelinghttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2In the last years enantioselective esterification of racemic ibuprofen performed in organic solvent media and catalyzed by lipases has been proposed as an effective way to increase the concentration of unesterified S-ibuprofen in the racemic mixture. In this contribution, a system free of organic solvent is proposed as a novel eco-friendly medium to perform the enantioselective enzymatic esterification of (R,S)-ibuprofen. Results showed that the reaction in excess of the esterifying alcohol in a system free of organic solvent is possible if the proper conditions are set. The effects of the amount of water present in the reaction medium, the volume of the alcohol used as acyl acceptor, the enzyme loading, and the reaction temperature, were alternatively analyzed in terms of the (conversion of ibuprofen towards the ester) reaction yield and enantiomeric excess achieved. Alcohol concentration showed to be determinant for both biocatalyst activity and enantioselectivity. The initial water content of reaction medium also showed to be a key parameter in a compromise between biocatalyst hydration and ester hydrolysis. By using 1 ml of ethanol as esterifying reagent, with an initial optimal water content of 4.8% v/v, at 45 °C, and with 160 mg of Novozym a total conversion of 62% and an enantiomeric excess of substrate of 54% were obtained in 72 hours of reaction.Fil: Foresti, María Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología En Polimeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología En Polimeros y Nanotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahia Blanca. Planta Piloto de Ingeniería Química (I). Grupo Vinculado al Plapiqui - Investigación y Desarrollo en Tecnología Química; ArgentinaFil: Galle, Marianela Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Ferreira, Maria Lujan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaFil: Briand, Laura Estefania. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaJohn Wiley & Sons Ltd2009-05-13info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/22921Foresti, María Laura; Galle, Marianela Edith; Ferreira, Maria Lujan; Briand, Laura Estefania; Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects; John Wiley & Sons Ltd; Journal of Chemical Technology and Biotechnology; 84; 10; 13-5-2009; 1461-14730268-2575CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/jctb.2200info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/jctb.2200/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:49:18Zoai:ri.conicet.gov.ar:11336/22921instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:49:18.905CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects
title Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects
spellingShingle Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects
Foresti, María Laura
Ibuprofeno
Lipase
Enantioselective
Esterification
Molecular Modeling
title_short Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects
title_full Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects
title_fullStr Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects
title_full_unstemmed Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects
title_sort Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects
dc.creator.none.fl_str_mv Foresti, María Laura
Galle, Marianela Edith
Ferreira, Maria Lujan
Briand, Laura Estefania
author Foresti, María Laura
author_facet Foresti, María Laura
Galle, Marianela Edith
Ferreira, Maria Lujan
Briand, Laura Estefania
author_role author
author2 Galle, Marianela Edith
Ferreira, Maria Lujan
Briand, Laura Estefania
author2_role author
author
author
dc.subject.none.fl_str_mv Ibuprofeno
Lipase
Enantioselective
Esterification
Molecular Modeling
topic Ibuprofeno
Lipase
Enantioselective
Esterification
Molecular Modeling
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv In the last years enantioselective esterification of racemic ibuprofen performed in organic solvent media and catalyzed by lipases has been proposed as an effective way to increase the concentration of unesterified S-ibuprofen in the racemic mixture. In this contribution, a system free of organic solvent is proposed as a novel eco-friendly medium to perform the enantioselective enzymatic esterification of (R,S)-ibuprofen. Results showed that the reaction in excess of the esterifying alcohol in a system free of organic solvent is possible if the proper conditions are set. The effects of the amount of water present in the reaction medium, the volume of the alcohol used as acyl acceptor, the enzyme loading, and the reaction temperature, were alternatively analyzed in terms of the (conversion of ibuprofen towards the ester) reaction yield and enantiomeric excess achieved. Alcohol concentration showed to be determinant for both biocatalyst activity and enantioselectivity. The initial water content of reaction medium also showed to be a key parameter in a compromise between biocatalyst hydration and ester hydrolysis. By using 1 ml of ethanol as esterifying reagent, with an initial optimal water content of 4.8% v/v, at 45 °C, and with 160 mg of Novozym a total conversion of 62% and an enantiomeric excess of substrate of 54% were obtained in 72 hours of reaction.
Fil: Foresti, María Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología En Polimeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología En Polimeros y Nanotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahia Blanca. Planta Piloto de Ingeniería Química (I). Grupo Vinculado al Plapiqui - Investigación y Desarrollo en Tecnología Química; Argentina
Fil: Galle, Marianela Edith. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Ferreira, Maria Lujan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Briand, Laura Estefania. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
description In the last years enantioselective esterification of racemic ibuprofen performed in organic solvent media and catalyzed by lipases has been proposed as an effective way to increase the concentration of unesterified S-ibuprofen in the racemic mixture. In this contribution, a system free of organic solvent is proposed as a novel eco-friendly medium to perform the enantioselective enzymatic esterification of (R,S)-ibuprofen. Results showed that the reaction in excess of the esterifying alcohol in a system free of organic solvent is possible if the proper conditions are set. The effects of the amount of water present in the reaction medium, the volume of the alcohol used as acyl acceptor, the enzyme loading, and the reaction temperature, were alternatively analyzed in terms of the (conversion of ibuprofen towards the ester) reaction yield and enantiomeric excess achieved. Alcohol concentration showed to be determinant for both biocatalyst activity and enantioselectivity. The initial water content of reaction medium also showed to be a key parameter in a compromise between biocatalyst hydration and ester hydrolysis. By using 1 ml of ethanol as esterifying reagent, with an initial optimal water content of 4.8% v/v, at 45 °C, and with 160 mg of Novozym a total conversion of 62% and an enantiomeric excess of substrate of 54% were obtained in 72 hours of reaction.
publishDate 2009
dc.date.none.fl_str_mv 2009-05-13
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/22921
Foresti, María Laura; Galle, Marianela Edith; Ferreira, Maria Lujan; Briand, Laura Estefania; Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects; John Wiley & Sons Ltd; Journal of Chemical Technology and Biotechnology; 84; 10; 13-5-2009; 1461-1473
0268-2575
CONICET Digital
CONICET
url http://hdl.handle.net/11336/22921
identifier_str_mv Foresti, María Laura; Galle, Marianela Edith; Ferreira, Maria Lujan; Briand, Laura Estefania; Enantioselective esterification of racemic ibuprofen with ethanol as reactant and solvent catalyzed by immobilized lipase: experimental and molecular modeling aspects; John Wiley & Sons Ltd; Journal of Chemical Technology and Biotechnology; 84; 10; 13-5-2009; 1461-1473
0268-2575
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/jctb.2200
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/jctb.2200/abstract
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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