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dc.contributor.author
Quintana, Paula Gabriela
dc.contributor.author
Guillén, Marina
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Marciello, Marzia
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Valero, Francisco
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Palomo, Jose M.
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Baldessari, Alicia
dc.date.available
2019-02-19T17:59:02Z
dc.date.issued
2012-08
dc.identifier.citation
Quintana, Paula Gabriela; Guillén, Marina; Marciello, Marzia; Valero, Francisco; Palomo, Jose M.; et al.; Immobilized heterologous Rhizopus Oryzae lipase as an efficient catalyst in the acetylation of cortexolone; Wiley VCH Verlag; European Journal of Organic Chemistry; 23; 8-2012; 4306-4312
dc.identifier.issn
1434-193X
dc.identifier.uri
http://hdl.handle.net/11336/70443
dc.description.abstract
The enzymatic preparation of a monoacetyl derivative of the corticosteroid cortexolone, through a transesterification reaction, is described. The heterologous Rhizopus oryzae lipase, immobilized on three different supports, proved to be an efficient catalyst in the acylation reaction using a complex substrate such as cortexolone. Immobilization of the enzyme on Lewatit 1600 resin at pH = 7 and 25 °C was the best condition for catalysis of the acetylation reaction. The influence of various reaction parameters, such as the nature of the acetylating agent, the solvent, the temperature, and the ratios of acetylating agent to substrate, and enzyme to substrate, was evaluated. Using the response surface methodology and a central composite rotatable design, the specific yield of acetylated cortexolone was optimized by means of the study of the effect of the enzyme (E)/substrate (S) and the acylating agent (A)/substrate ratios. The ratios of 5 (E/S) and 31.6 (A/S) were predicted as the optimal values to reach the maximum specific yield of the product (P): 1.59 mmol P/mmol A·g E. The mild reaction conditions and low environmental impact make the biocatalytic procedure a convenient way to prepare the reported derivative of this biologically active steroid. The regioselective acetylation of cortexolone was achieved by using an immobilized heterologous Rhizopus oryzae lipase. The mild reaction conditions and low environmental impact make the biocatalytic procedure a convenient way to prepare the monoacetyl derivative of this biologically active steroid. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Wiley VCH Verlag
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Acylation
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Biocatalysis
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Enzymes
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Immobilization
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Steroids
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Supported Catalysts
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Otras Ciencias Químicas
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Immobilized heterologous Rhizopus Oryzae lipase as an efficient catalyst in the acetylation of cortexolone
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2019-01-09T14:20:32Z
dc.journal.number
23
dc.journal.pagination
4306-4312
dc.journal.pais
Alemania
dc.journal.ciudad
Weinheim
dc.description.fil
Fil: Quintana, Paula Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
dc.description.fil
Fil: Guillén, Marina. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Marciello, Marzia. Consejo Superior de Investigaciones Científicas; España
dc.description.fil
Fil: Valero, Francisco. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Palomo, Jose M.. Consejo Superior de Investigaciones Científicas; España
dc.description.fil
Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
dc.journal.title
European Journal of Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1002/ejoc.201200178
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201200178
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