Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid...
- Autores
- Foresti, María Laura; Ferreira, María Luján
- Año de publicación
- 2004
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- This paper presents the results of a MM2 study of the adsorption of oleic acid and ethanol/water in the tunnel and active-site models of lipases from Candida rugosa and Candida antarctica B. The role of an interface polar/no polar in the opening of C rugosa lipase's lid is also addressed, discussed and analyzed at the level of the conformational changes needed to achieve the lipase open form. The adsorption of oleic acid and alcohols considering C. antarctica B, a lipase not interfacially activated, is also presented. In this case, the tunnel is shorter than in case of C. rugosa lipase. Two different pockets can be visualized at the active site-tunnel model of C. antarctica B lipase: one for the acyl group and another for the alcohol. Wrong location of alcohol and oleic acid severely hinders reaction because it hinders the H-transfer to histidine, a key step in the reaction mechanism. Right location of alcohol decreases the possibility of alcohol inhibition. In the case of C. rugosa, no restrictions for ethanol/water location are found. For that lipase, a second adsorption site for oleic acid (outside the tunnel) is presented. This site is the exit tunnel of the ester product when oleic acid is adsorbed in the tunnel. Experimental results of our own that correlate with this study are presented. © 2004 American Chemical Society.
Fil: Foresti, María Laura. 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: Ferreira, María Luján. 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 - Materia
-
Dynamics Simulations
Lipase
Molecular Dynamics
Molecular Modelling
Polyester Synthesis
Rhizomucor Miehei - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/61955
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Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorptionForesti, María LauraFerreira, María LujánDynamics SimulationsLipaseMolecular DynamicsMolecular ModellingPolyester SynthesisRhizomucor Mieheihttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2This paper presents the results of a MM2 study of the adsorption of oleic acid and ethanol/water in the tunnel and active-site models of lipases from Candida rugosa and Candida antarctica B. The role of an interface polar/no polar in the opening of C rugosa lipase's lid is also addressed, discussed and analyzed at the level of the conformational changes needed to achieve the lipase open form. The adsorption of oleic acid and alcohols considering C. antarctica B, a lipase not interfacially activated, is also presented. In this case, the tunnel is shorter than in case of C. rugosa lipase. Two different pockets can be visualized at the active site-tunnel model of C. antarctica B lipase: one for the acyl group and another for the alcohol. Wrong location of alcohol and oleic acid severely hinders reaction because it hinders the H-transfer to histidine, a key step in the reaction mechanism. Right location of alcohol decreases the possibility of alcohol inhibition. In the case of C. rugosa, no restrictions for ethanol/water location are found. For that lipase, a second adsorption site for oleic acid (outside the tunnel) is presented. This site is the exit tunnel of the ester product when oleic acid is adsorbed in the tunnel. Experimental results of our own that correlate with this study are presented. © 2004 American Chemical Society.Fil: Foresti, María Laura. 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: Ferreira, María Luján. 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; ArgentinaAmerican Chemical Society2004-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/61955Foresti, María Laura; Ferreira, María Luján; Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption; American Chemical Society; Biomacromolecules; 5; 6; 11-2004; 2366-23751525-7797CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/bm049688oinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/bm049688oinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:07Zoai:ri.conicet.gov.ar:11336/61955instacron: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:34982025-09-29 10:33:07.878CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption |
title |
Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption |
spellingShingle |
Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption Foresti, María Laura Dynamics Simulations Lipase Molecular Dynamics Molecular Modelling Polyester Synthesis Rhizomucor Miehei |
title_short |
Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption |
title_full |
Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption |
title_fullStr |
Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption |
title_full_unstemmed |
Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption |
title_sort |
Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption |
dc.creator.none.fl_str_mv |
Foresti, María Laura Ferreira, María Luján |
author |
Foresti, María Laura |
author_facet |
Foresti, María Laura Ferreira, María Luján |
author_role |
author |
author2 |
Ferreira, María Luján |
author2_role |
author |
dc.subject.none.fl_str_mv |
Dynamics Simulations Lipase Molecular Dynamics Molecular Modelling Polyester Synthesis Rhizomucor Miehei |
topic |
Dynamics Simulations Lipase Molecular Dynamics Molecular Modelling Polyester Synthesis Rhizomucor Miehei |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/2.9 https://purl.org/becyt/ford/2 |
dc.description.none.fl_txt_mv |
This paper presents the results of a MM2 study of the adsorption of oleic acid and ethanol/water in the tunnel and active-site models of lipases from Candida rugosa and Candida antarctica B. The role of an interface polar/no polar in the opening of C rugosa lipase's lid is also addressed, discussed and analyzed at the level of the conformational changes needed to achieve the lipase open form. The adsorption of oleic acid and alcohols considering C. antarctica B, a lipase not interfacially activated, is also presented. In this case, the tunnel is shorter than in case of C. rugosa lipase. Two different pockets can be visualized at the active site-tunnel model of C. antarctica B lipase: one for the acyl group and another for the alcohol. Wrong location of alcohol and oleic acid severely hinders reaction because it hinders the H-transfer to histidine, a key step in the reaction mechanism. Right location of alcohol decreases the possibility of alcohol inhibition. In the case of C. rugosa, no restrictions for ethanol/water location are found. For that lipase, a second adsorption site for oleic acid (outside the tunnel) is presented. This site is the exit tunnel of the ester product when oleic acid is adsorbed in the tunnel. Experimental results of our own that correlate with this study are presented. © 2004 American Chemical Society. Fil: Foresti, María Laura. 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: Ferreira, María Luján. 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 |
description |
This paper presents the results of a MM2 study of the adsorption of oleic acid and ethanol/water in the tunnel and active-site models of lipases from Candida rugosa and Candida antarctica B. The role of an interface polar/no polar in the opening of C rugosa lipase's lid is also addressed, discussed and analyzed at the level of the conformational changes needed to achieve the lipase open form. The adsorption of oleic acid and alcohols considering C. antarctica B, a lipase not interfacially activated, is also presented. In this case, the tunnel is shorter than in case of C. rugosa lipase. Two different pockets can be visualized at the active site-tunnel model of C. antarctica B lipase: one for the acyl group and another for the alcohol. Wrong location of alcohol and oleic acid severely hinders reaction because it hinders the H-transfer to histidine, a key step in the reaction mechanism. Right location of alcohol decreases the possibility of alcohol inhibition. In the case of C. rugosa, no restrictions for ethanol/water location are found. For that lipase, a second adsorption site for oleic acid (outside the tunnel) is presented. This site is the exit tunnel of the ester product when oleic acid is adsorbed in the tunnel. Experimental results of our own that correlate with this study are presented. © 2004 American Chemical Society. |
publishDate |
2004 |
dc.date.none.fl_str_mv |
2004-11 |
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/11336/61955 Foresti, María Laura; Ferreira, María Luján; Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption; American Chemical Society; Biomacromolecules; 5; 6; 11-2004; 2366-2375 1525-7797 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/61955 |
identifier_str_mv |
Foresti, María Laura; Ferreira, María Luján; Computational approach to solvent-free synthesis of ethyl oleate using Candida rugosa and Candida antarctica B lipases. I. Interfacial activation and substrate (ethanol, oleic acid) adsorption; American Chemical Society; Biomacromolecules; 5; 6; 11-2004; 2366-2375 1525-7797 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1021/bm049688o info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/bm049688o |
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 application/pdf |
dc.publisher.none.fl_str_mv |
American Chemical Society |
publisher.none.fl_str_mv |
American Chemical Society |
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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1844614346159685632 |
score |
13.070432 |