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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paper:paper_14246376_v2005_n12_p175_Rustoy2023-06-08T16:13:54Z Regioselective enzymatic synthesis of estradiol 17-fatty acid esters Rustoy, Eduardo Miguel Baldessari, Alicia 3,17-β-estradiol esters Enzymatic acylation and alcoholysis Lipases 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. 2005 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p175_Rustoy http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
3,17-β-estradiol esters Enzymatic acylation and alcoholysis Lipases |
| spellingShingle |
3,17-β-estradiol esters Enzymatic acylation and alcoholysis Lipases Rustoy, Eduardo Miguel Baldessari, Alicia 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. |
| author |
Rustoy, Eduardo Miguel Baldessari, Alicia |
| author_facet |
Rustoy, Eduardo Miguel 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 |
| publishDate |
2005 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p175_Rustoy http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p175_Rustoy |
| work_keys_str_mv |
AT rustoyeduardomiguel regioselectiveenzymaticsynthesisofestradiol17fattyacidesters AT baldessarialicia regioselectiveenzymaticsynthesisofestradiol17fattyacidesters |
| _version_ |
1768544053704523776 |