Regioselective enzymatic synthesis of estradiol 17-fatty acid esters
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 vari...
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ftconicet:oai:ri.conicet.gov.ar:11336/92316 2023-10-09T21:47:14+02:00 Regioselective enzymatic synthesis of estradiol 17-fatty acid esters Rustoy, Eduardo Miguel Ruiz Arias, Ignacio Edgardo Baldessari, Alicia application/pdf http://hdl.handle.net/11336/92316 eng eng Arkat USA info:eu-repo/semantics/altIdentifier/url/https://www.arkat-usa.org/get-file/19295 http://hdl.handle.net/11336/92316 Rustoy, Eduardo Miguel; Ruiz Arias, Ignacio Edgardo; Baldessari, Alicia; Regioselective enzymatic synthesis of estradiol 17-fatty acid esters; Arkat USA; Arkivoc; 2005; XII; 11-2005; 175-188 1424-6376 CONICET Digital CONICET info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ Lipase Enzymatic acilation and alcoholysis 3,17- ß-estradiol https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion ftconicet 2023-09-24T19:15:10Z 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. Fil: Rustoy, Eduardo Miguel. 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 Fil: Ruiz Arias, Ignacio Edgardo. 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 Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en ... 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) Alicia ENVELOPE(-63.483,-63.483,-64.833,-64.833) Edgardo ENVELOPE(-64.517,-64.517,-64.833,-64.833) |
institution |
Open Polar |
collection |
CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) |
op_collection_id |
ftconicet |
language |
English |
topic |
Lipase Enzymatic acilation and alcoholysis 3,17- ß-estradiol https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
spellingShingle |
Lipase Enzymatic acilation and alcoholysis 3,17- ß-estradiol https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 Rustoy, Eduardo Miguel Ruiz Arias, Ignacio Edgardo Baldessari, Alicia Regioselective enzymatic synthesis of estradiol 17-fatty acid esters |
topic_facet |
Lipase Enzymatic acilation and alcoholysis 3,17- ß-estradiol https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
description |
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. Fil: Rustoy, Eduardo Miguel. 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 Fil: Ruiz Arias, Ignacio Edgardo. 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 Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en ... |
format |
Article in Journal/Newspaper |
author |
Rustoy, Eduardo Miguel Ruiz Arias, Ignacio Edgardo Baldessari, Alicia |
author_facet |
Rustoy, Eduardo Miguel Ruiz Arias, Ignacio Edgardo Baldessari, Alicia |
author_sort |
Rustoy, Eduardo Miguel |
title |
Regioselective enzymatic synthesis of estradiol 17-fatty acid esters |
title_short |
Regioselective enzymatic synthesis of estradiol 17-fatty acid esters |
title_full |
Regioselective enzymatic synthesis of estradiol 17-fatty acid esters |
title_fullStr |
Regioselective enzymatic synthesis of estradiol 17-fatty acid esters |
title_full_unstemmed |
Regioselective enzymatic synthesis of estradiol 17-fatty acid esters |
title_sort |
regioselective enzymatic synthesis of estradiol 17-fatty acid esters |
publisher |
Arkat USA |
url |
http://hdl.handle.net/11336/92316 |
long_lat |
ENVELOPE(-61.250,-61.250,-62.633,-62.633) ENVELOPE(-63.483,-63.483,-64.833,-64.833) ENVELOPE(-64.517,-64.517,-64.833,-64.833) |
geographic |
Argentina Rugosa Alicia Edgardo |
geographic_facet |
Argentina Rugosa Alicia Edgardo |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/url/https://www.arkat-usa.org/get-file/19295 http://hdl.handle.net/11336/92316 Rustoy, Eduardo Miguel; Ruiz Arias, Ignacio Edgardo; Baldessari, Alicia; Regioselective enzymatic synthesis of estradiol 17-fatty acid esters; Arkat USA; Arkivoc; 2005; XII; 11-2005; 175-188 1424-6376 CONICET Digital CONICET |
op_rights |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
_version_ |
1779310197750104064 |