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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2005
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy https://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p175_Rustoy_oai |
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I28-R145-paper_14246376_v2005_n12_p175_Rustoy_oai2024-08-16 Rustoy, E.M. Ruiz Arias, I.E. Baldessari, A. 2005 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. application/pdf http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar Arkivoc 2005;2005(12):175-188 3,17-β-estradiol esters Enzymatic acylation and alcoholysis Lipases Regioselective enzymatic synthesis of estradiol 17-fatty acid esters info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion https://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p175_Rustoy_oai |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-145 |
| collection |
Repositorio Digital de la Universidad de Buenos Aires (UBA) |
| 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. |
| format |
Artículo Artículo publishedVersion |
| 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 |
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy https://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p175_Rustoy_oai |
| work_keys_str_mv |
AT rustoyem regioselectiveenzymaticsynthesisofestradiol17fattyacidesters AT ruizariasie regioselectiveenzymaticsynthesisofestradiol17fattyacidesters AT baldessaria regioselectiveenzymaticsynthesisofestradiol17fattyacidesters |
| _version_ |
1809357117952360448 |