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Abstract:

A series of acyl esters of 3,17-β-estradiol has been prepared by an enzymatic methodology. Eleven 17-monoacyl products (five novel compounds) were obtained in a highly regioselective way by acylation of 3,17-β-estradiol or by alcoholysis of the corresponding diacyl derivatives. The influence of various reaction parameters such as molar ratio, enzyme:substrate ratio and temperature was evaluated. Among the tested lipases, Candida rugosa lipase appeared to be the most appropriate in monoacylation and lipase from Candida antarctica in alcoholysis. The advantages presented by this methodology such as mild reaction conditions, economy and low environmental impact, make the biocatalysis a convenient way to prepare monoacyl derivatives of 3,17-β-estradiol containing the aromatic 3-hydroxyl group free. Some of these compounds are recongnized as useful products in the pharmaceutical industry. ©ARKAT.

Registro:

Documento: Artículo
Título:Regioselective enzymatic synthesis of estradiol 17-fatty acid esters
Autor:Rustoy, E.M.; Ruiz Arias, I.E.; Baldessari, A.
Filiación:Departamento de Química Organica Y UMYMFOR, Facultad de Ciencias Exactas Y Naturales, Cuidad Universitaria, 1428, Buenos Aires, Argentina
Palabras clave:3,17-β-estradiol esters; Enzymatic acylation and alcoholysis; Lipases
Año:2005
Volumen:2005
Número:12
Página de inicio:175
Página de fin:188
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:14246376
PDF:https://bibliotecadigital.exactas.uba.ar/download/paper/paper_14246376_v2005_n12_p175_Rustoy.pdf
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p175_Rustoy

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Citas:

---------- APA ----------
Rustoy, E.M., Ruiz Arias, I.E. & Baldessari, A. (2005) . Regioselective enzymatic synthesis of estradiol 17-fatty acid esters. Arkivoc, 2005(12), 175-188.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p175_Rustoy [ ]
---------- CHICAGO ----------
Rustoy, E.M., Ruiz Arias, I.E., Baldessari, A. "Regioselective enzymatic synthesis of estradiol 17-fatty acid esters" . Arkivoc 2005, no. 12 (2005) : 175-188.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p175_Rustoy [ ]
---------- MLA ----------
Rustoy, E.M., Ruiz Arias, I.E., Baldessari, A. "Regioselective enzymatic synthesis of estradiol 17-fatty acid esters" . Arkivoc, vol. 2005, no. 12, 2005, pp. 175-188.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p175_Rustoy [ ]
---------- VANCOUVER ----------
Rustoy, E.M., Ruiz Arias, I.E., Baldessari, A. Regioselective enzymatic synthesis of estradiol 17-fatty acid esters. Arkivoc. 2005;2005(12):175-188.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p175_Rustoy [ ]