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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ftunbuenosairrdi:oai:RDI UBA:artiaex:paper_14246376_v2005_n12_p175_Rustoy_oai 2023-05-15T13:54:03+02:00 Regioselective enzymatic synthesis of estradiol 17-fatty acid esters Rustoy, E.M. Ruiz Arias, I.E. Baldessari, A. 2005 application/pdf https://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy http://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p175_Rustoy_oai unknown http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy http://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p175_Rustoy_oai info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar CC-BY Arkivoc 2005;2005(12):175-188 3,17-β-estradiol esters Enzymatic acylation and alcoholysis Lipases info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion 2005 ftunbuenosairrdi https://doi.org/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy 2020-10-22T00:10:07Z 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. Fil:Rustoy, E.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Baldessari, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Article in Journal/Newspaper Antarc* Antarctica Repositorio Digital Institucional - Universidad de Buenos Aires (RDI UBA) Argentina Rugosa ENVELOPE(-61.250,-61.250,-62.633,-62.633) |
institution |
Open Polar |
collection |
Repositorio Digital Institucional - Universidad de Buenos Aires (RDI UBA) |
op_collection_id |
ftunbuenosairrdi |
language |
unknown |
topic |
3,17-β-estradiol esters Enzymatic acylation and alcoholysis Lipases |
spellingShingle |
3,17-β-estradiol esters Enzymatic acylation and alcoholysis Lipases Rustoy, E.M. Ruiz Arias, I.E. Baldessari, A. Regioselective enzymatic synthesis of estradiol 17-fatty acid esters |
topic_facet |
3,17-β-estradiol esters Enzymatic acylation and alcoholysis Lipases |
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. ©ARKAT. Fil:Rustoy, E.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Baldessari, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. |
format |
Article in Journal/Newspaper |
author |
Rustoy, E.M. Ruiz Arias, I.E. Baldessari, A. |
author_facet |
Rustoy, E.M. Ruiz Arias, I.E. Baldessari, A. |
author_sort |
Rustoy, E.M. |
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 |
publishDate |
2005 |
url |
https://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy http://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p175_Rustoy_oai |
long_lat |
ENVELOPE(-61.250,-61.250,-62.633,-62.633) |
geographic |
Argentina Rugosa |
geographic_facet |
Argentina Rugosa |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Arkivoc 2005;2005(12):175-188 |
op_relation |
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy http://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p175_Rustoy_oai |
op_rights |
info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar |
op_rightsnorm |
CC-BY |
op_doi |
https://doi.org/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy |
_version_ |
1766259555792060416 |