Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone
A series of fatty acid derivatives of hydrocortisone has been prepared by an enzymatic methodology. Nine 21-monoacyl products and one 3,11,17-triacetyl derivative, nine of them novel compounds, were obtained in a highly regioselective way through lipase-catalyzed esterification, transesterification...
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ftunibueairesbd:paper:paper_0039128X_v74_n13-14_p1007_Quintana 2023-05-15T13:42:26+02:00 Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone 2009 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v74_n13-14_p1007_Quintana https://hdl.handle.net/20.500.12110/paper_0039128X_v74_n13-14_p1007_Quintana unknown https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v74_n13-14_p1007_Quintana http://hdl.handle.net/20.500.12110/paper_0039128X_v74_n13-14_p1007_Quintana Hydrocortisone fatty acid esters Lipase-catalyzed reactions 21 9 octadecanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 9,12 octadecadienoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 9,12,15 octadecatrienoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 acetoxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 decanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 hexanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 octadecanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 octanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 3,11beta,17alpha triacetoxy 21 hydroxypregna 3,5 dien 20 one fatty acid ester hydrocortisone derivative hydrocortisone fatty acid ester derivative solvent triacylglycerol lipase unclassified drug alcoholysis article biocatalyst Candida antarctica catalysis enzyme substrate esterification methodology stereochemistry temperature transesterification Candida Fatty Acids Hydrocortisone Lipase 2009 ftunibueairesbd https://doi.org/20.500.12110/paper_0039128X_v74_n13-14_p1007_Quintana 2023-02-16T01:57:50Z A series of fatty acid derivatives of hydrocortisone has been prepared by an enzymatic methodology. Nine 21-monoacyl products and one 3,11,17-triacetyl derivative, nine of them novel compounds, were obtained in a highly regioselective way through lipase-catalyzed esterification, transesterification and alcoholysis reactions. The influence of various reaction parameters such as acylating agent: substrate ratio, enzyme: substrate ratio, solvent, temperature and nature of acylating agent and alcohol was evaluated. Among the tested lipases, Candida antarctica lipase appeared to be the most appropriate and showed a high efficient behavior especially in a one-pot transesterification. The advantages presented by this methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to prepare acyl derivatives of hydrocortisone. These lipophilic compounds are potential products in the pharmaceutical industry. © 2009 Elsevier Inc. All rights reserved. Other/Unknown Material Antarc* Antarctica Biblioteca Digital FCEN-UBA (Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires) |
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Biblioteca Digital FCEN-UBA (Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires) |
op_collection_id |
ftunibueairesbd |
language |
unknown |
topic |
Hydrocortisone fatty acid esters Lipase-catalyzed reactions 21 9 octadecanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 9,12 octadecadienoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 9,12,15 octadecatrienoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 acetoxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 decanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 hexanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 octadecanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 octanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 3,11beta,17alpha triacetoxy 21 hydroxypregna 3,5 dien 20 one fatty acid ester hydrocortisone derivative hydrocortisone fatty acid ester derivative solvent triacylglycerol lipase unclassified drug alcoholysis article biocatalyst Candida antarctica catalysis enzyme substrate esterification methodology stereochemistry temperature transesterification Candida Fatty Acids Hydrocortisone Lipase |
spellingShingle |
Hydrocortisone fatty acid esters Lipase-catalyzed reactions 21 9 octadecanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 9,12 octadecadienoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 9,12,15 octadecatrienoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 acetoxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 decanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 hexanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 octadecanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 octanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 3,11beta,17alpha triacetoxy 21 hydroxypregna 3,5 dien 20 one fatty acid ester hydrocortisone derivative hydrocortisone fatty acid ester derivative solvent triacylglycerol lipase unclassified drug alcoholysis article biocatalyst Candida antarctica catalysis enzyme substrate esterification methodology stereochemistry temperature transesterification Candida Fatty Acids Hydrocortisone Lipase Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
topic_facet |
Hydrocortisone fatty acid esters Lipase-catalyzed reactions 21 9 octadecanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 9,12 octadecadienoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 9,12,15 octadecatrienoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 acetoxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 decanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 hexanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 octadecanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 21 octanoyloxy 11beta,17alpha dihydroxypregn 4 en 3,20 dione 3,11beta,17alpha triacetoxy 21 hydroxypregna 3,5 dien 20 one fatty acid ester hydrocortisone derivative hydrocortisone fatty acid ester derivative solvent triacylglycerol lipase unclassified drug alcoholysis article biocatalyst Candida antarctica catalysis enzyme substrate esterification methodology stereochemistry temperature transesterification Candida Fatty Acids Hydrocortisone Lipase |
description |
A series of fatty acid derivatives of hydrocortisone has been prepared by an enzymatic methodology. Nine 21-monoacyl products and one 3,11,17-triacetyl derivative, nine of them novel compounds, were obtained in a highly regioselective way through lipase-catalyzed esterification, transesterification and alcoholysis reactions. The influence of various reaction parameters such as acylating agent: substrate ratio, enzyme: substrate ratio, solvent, temperature and nature of acylating agent and alcohol was evaluated. Among the tested lipases, Candida antarctica lipase appeared to be the most appropriate and showed a high efficient behavior especially in a one-pot transesterification. The advantages presented by this methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to prepare acyl derivatives of hydrocortisone. These lipophilic compounds are potential products in the pharmaceutical industry. © 2009 Elsevier Inc. All rights reserved. |
title |
Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
title_short |
Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
title_full |
Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
title_fullStr |
Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
title_full_unstemmed |
Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
title_sort |
lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
publishDate |
2009 |
url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v74_n13-14_p1007_Quintana https://hdl.handle.net/20.500.12110/paper_0039128X_v74_n13-14_p1007_Quintana |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v74_n13-14_p1007_Quintana http://hdl.handle.net/20.500.12110/paper_0039128X_v74_n13-14_p1007_Quintana |
op_doi |
https://doi.org/20.500.12110/paper_0039128X_v74_n13-14_p1007_Quintana |
_version_ |
1766167750798999552 |