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
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, discu...
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ftconicet:oai:ri.conicet.gov.ar:11336/61955 2023-10-09T21:46:51+02:00 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 Ferreira, María Luján application/pdf http://hdl.handle.net/11336/61955 eng eng American Chemical Society info:eu-repo/semantics/altIdentifier/doi/10.1021/bm049688o info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/bm049688o 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 info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ Dynamics Simulations Lipase Molecular Dynamics Molecular Modelling Polyester Synthesis Rhizomucor Miehei https://purl.org/becyt/ford/2.9 https://purl.org/becyt/ford/2 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion ftconicet https://doi.org/10.1021/bm049688o 2023-09-24T20:11:29Z 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 Article in Journal/Newspaper Antarc* Antarctica CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) Argentina Rugosa ENVELOPE(-61.250,-61.250,-62.633,-62.633) Ferreira ENVELOPE(-62.050,-62.050,-64.600,-64.600) Biomacromolecules 5 6 2366 2375 |
institution |
Open Polar |
collection |
CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) |
op_collection_id |
ftconicet |
language |
English |
topic |
Dynamics Simulations Lipase Molecular Dynamics Molecular Modelling Polyester Synthesis Rhizomucor Miehei https://purl.org/becyt/ford/2.9 https://purl.org/becyt/ford/2 |
spellingShingle |
Dynamics Simulations Lipase Molecular Dynamics Molecular Modelling Polyester Synthesis Rhizomucor Miehei https://purl.org/becyt/ford/2.9 https://purl.org/becyt/ford/2 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 |
topic_facet |
Dynamics Simulations Lipase Molecular Dynamics Molecular Modelling Polyester Synthesis Rhizomucor Miehei https://purl.org/becyt/ford/2.9 https://purl.org/becyt/ford/2 |
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. 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 |
format |
Article in Journal/Newspaper |
author |
Foresti, María Laura Ferreira, María Luján |
author_facet |
Foresti, María Laura Ferreira, María Luján |
author_sort |
Foresti, María Laura |
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 |
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 |
publisher |
American Chemical Society |
url |
http://hdl.handle.net/11336/61955 |
long_lat |
ENVELOPE(-61.250,-61.250,-62.633,-62.633) ENVELOPE(-62.050,-62.050,-64.600,-64.600) |
geographic |
Argentina Rugosa Ferreira |
geographic_facet |
Argentina Rugosa Ferreira |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1021/bm049688o info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/bm049688o 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 |
op_rights |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
op_doi |
https://doi.org/10.1021/bm049688o |
container_title |
Biomacromolecules |
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5 |
container_issue |
6 |
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2366 |
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2375 |
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1779309425130995712 |