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Quintana, P.G.; Guillén, M.; Marciello, M.; Valero, F.; Palomo, J.M.; Baldessari, A. "Immobilized heterologous Rhizopus Oryzae lipase as an efficient catalyst in the acetylation of cortexolone" (2012) European Journal of Organic Chemistry(23):4306-4312
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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.

Registro:

Documento: Artículo
Título:Immobilized heterologous Rhizopus Oryzae lipase as an efficient catalyst in the acetylation of cortexolone
Autor:Quintana, P.G.; Guillén, M.; Marciello, M.; Valero, F.; Palomo, J.M.; Baldessari, A.
Filiación:Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Universidad de Buenos Aires, C1428EGA, Buenos Aires, Argentina
Departament d'Enginyeria Química, EE, Universitat Autònoma de Barcelona, 08193 Bellaterra, Barcelona, Spain
Departamento de Biocatálisis, Instituto de Catálisis (CSIC), Campus UAM Cantoblanco, 28049 Madrid, Spain
Palabras clave:Acylation; Biocatalysis; Enzymes; Immobilization; Steroids; Supported catalysts
Año:2012
Número:23
Página de inicio:4306
Página de fin:4312
DOI: http://dx.doi.org/10.1002/ejoc.201200178
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n23_p4306_Quintana

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Citas:

---------- APA ----------
Quintana, P.G., Guillén, M., Marciello, M., Valero, F., Palomo, J.M. & Baldessari, A. (2012) . Immobilized heterologous Rhizopus Oryzae lipase as an efficient catalyst in the acetylation of cortexolone. European Journal of Organic Chemistry(23), 4306-4312.
http://dx.doi.org/10.1002/ejoc.201200178
---------- CHICAGO ----------
Quintana, P.G., Guillén, M., Marciello, M., Valero, F., Palomo, J.M., Baldessari, A. "Immobilized heterologous Rhizopus Oryzae lipase as an efficient catalyst in the acetylation of cortexolone" . European Journal of Organic Chemistry, no. 23 (2012) : 4306-4312.
http://dx.doi.org/10.1002/ejoc.201200178
---------- MLA ----------
Quintana, P.G., Guillén, M., Marciello, M., Valero, F., Palomo, J.M., Baldessari, A. "Immobilized heterologous Rhizopus Oryzae lipase as an efficient catalyst in the acetylation of cortexolone" . European Journal of Organic Chemistry, no. 23, 2012, pp. 4306-4312.
http://dx.doi.org/10.1002/ejoc.201200178
---------- VANCOUVER ----------
Quintana, P.G., Guillén, M., Marciello, M., Valero, F., Palomo, J.M., Baldessari, A. Immobilized heterologous Rhizopus Oryzae lipase as an efficient catalyst in the acetylation of cortexolone. Eur. J. Org. Chem. 2012(23):4306-4312.
http://dx.doi.org/10.1002/ejoc.201200178