Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone
A series of acyl esters derivatives of dehydroepiandrosterone have been prepared by an enzymatic methodology. The acyl chain had a length that varied from two to eighteen carbon atoms. The C18 derivative could be saturated or unsaturated. Following this biocatalytic approach we have also obtained a...
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todo:paper_10242422_v22_n3_p215_Bruttomesso2023-10-03T15:56:52Z Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone Bruttomesso, A.C. Tiscornia, A. Baldessari, A. Dehydroepiandrosterone Enzymatic acylation Lipase-catalyzed Biocatalysts Carbon Catalysis Environmental impact Esterification Acyl derivatives Transesterification reactions Esters 3beta (3 chloropropoxy) 5 androsten 17 one 3beta 9 octadecanoyloxy 5 androsten 17 one 3beta 9,12 octadecadienoyloxy 5 androsten 17 one 3beta 9,12,15 octadecatrienoyloxy 5 androsten 17 one 3beta acetoxy 5 androsten 17 one 3beta butyroxy 5 androsten 17 one 3beta dodecanoyloxy 5 androsten 17 one 3beta hexadecanoyloxy 5 androsten 17 one 3beta hexanoyloxy 5 androsten 17 one 3beta octadecanoyloxy 5 androsten 17 one 3beta propoxy 5 androsten 17 one carboxylic acid derivative ester derivative prasterone steroid triacylglycerol lipase unclassified drug acylation analytic method article biocatalyst chemical reaction kinetics controlled study drug activity drug structure drug synthesis economic aspect environmental impact esterification quantum yield structure analysis transesterification A series of acyl esters derivatives of dehydroepiandrosterone have been prepared by an enzymatic methodology. The acyl chain had a length that varied from two to eighteen carbon atoms. The C18 derivative could be saturated or unsaturated. Following this biocatalytic approach we have also obtained a chloropropionyl derivative. We have observed that several lipases catalyzed esterification and transesterification reactions of dehydroepiandrosterone with carboxylic acids or alkyl carboxylates. The advantages presented by this methodology such as mild reaction conditions, economy and low environmental impact, make biocatalysis a convenient way to prepare acyl derivatives of DHEA with biological activity. © 2004 Taylor & Francis Ltd. Fil:Bruttomesso, A.C. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_10242422_v22_n3_p215_Bruttomesso |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Dehydroepiandrosterone Enzymatic acylation Lipase-catalyzed Biocatalysts Carbon Catalysis Environmental impact Esterification Acyl derivatives Transesterification reactions Esters 3beta (3 chloropropoxy) 5 androsten 17 one 3beta 9 octadecanoyloxy 5 androsten 17 one 3beta 9,12 octadecadienoyloxy 5 androsten 17 one 3beta 9,12,15 octadecatrienoyloxy 5 androsten 17 one 3beta acetoxy 5 androsten 17 one 3beta butyroxy 5 androsten 17 one 3beta dodecanoyloxy 5 androsten 17 one 3beta hexadecanoyloxy 5 androsten 17 one 3beta hexanoyloxy 5 androsten 17 one 3beta octadecanoyloxy 5 androsten 17 one 3beta propoxy 5 androsten 17 one carboxylic acid derivative ester derivative prasterone steroid triacylglycerol lipase unclassified drug acylation analytic method article biocatalyst chemical reaction kinetics controlled study drug activity drug structure drug synthesis economic aspect environmental impact esterification quantum yield structure analysis transesterification |
| spellingShingle |
Dehydroepiandrosterone Enzymatic acylation Lipase-catalyzed Biocatalysts Carbon Catalysis Environmental impact Esterification Acyl derivatives Transesterification reactions Esters 3beta (3 chloropropoxy) 5 androsten 17 one 3beta 9 octadecanoyloxy 5 androsten 17 one 3beta 9,12 octadecadienoyloxy 5 androsten 17 one 3beta 9,12,15 octadecatrienoyloxy 5 androsten 17 one 3beta acetoxy 5 androsten 17 one 3beta butyroxy 5 androsten 17 one 3beta dodecanoyloxy 5 androsten 17 one 3beta hexadecanoyloxy 5 androsten 17 one 3beta hexanoyloxy 5 androsten 17 one 3beta octadecanoyloxy 5 androsten 17 one 3beta propoxy 5 androsten 17 one carboxylic acid derivative ester derivative prasterone steroid triacylglycerol lipase unclassified drug acylation analytic method article biocatalyst chemical reaction kinetics controlled study drug activity drug structure drug synthesis economic aspect environmental impact esterification quantum yield structure analysis transesterification Bruttomesso, A.C. Tiscornia, A. Baldessari, A. Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone |
| topic_facet |
Dehydroepiandrosterone Enzymatic acylation Lipase-catalyzed Biocatalysts Carbon Catalysis Environmental impact Esterification Acyl derivatives Transesterification reactions Esters 3beta (3 chloropropoxy) 5 androsten 17 one 3beta 9 octadecanoyloxy 5 androsten 17 one 3beta 9,12 octadecadienoyloxy 5 androsten 17 one 3beta 9,12,15 octadecatrienoyloxy 5 androsten 17 one 3beta acetoxy 5 androsten 17 one 3beta butyroxy 5 androsten 17 one 3beta dodecanoyloxy 5 androsten 17 one 3beta hexadecanoyloxy 5 androsten 17 one 3beta hexanoyloxy 5 androsten 17 one 3beta octadecanoyloxy 5 androsten 17 one 3beta propoxy 5 androsten 17 one carboxylic acid derivative ester derivative prasterone steroid triacylglycerol lipase unclassified drug acylation analytic method article biocatalyst chemical reaction kinetics controlled study drug activity drug structure drug synthesis economic aspect environmental impact esterification quantum yield structure analysis transesterification |
| description |
A series of acyl esters derivatives of dehydroepiandrosterone have been prepared by an enzymatic methodology. The acyl chain had a length that varied from two to eighteen carbon atoms. The C18 derivative could be saturated or unsaturated. Following this biocatalytic approach we have also obtained a chloropropionyl derivative. We have observed that several lipases catalyzed esterification and transesterification reactions of dehydroepiandrosterone with carboxylic acids or alkyl carboxylates. The advantages presented by this methodology such as mild reaction conditions, economy and low environmental impact, make biocatalysis a convenient way to prepare acyl derivatives of DHEA with biological activity. © 2004 Taylor & Francis Ltd. |
| format |
JOUR |
| author |
Bruttomesso, A.C. Tiscornia, A. Baldessari, A. |
| author_facet |
Bruttomesso, A.C. Tiscornia, A. Baldessari, A. |
| author_sort |
Bruttomesso, A.C. |
| title |
Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone |
| title_short |
Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone |
| title_full |
Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone |
| title_fullStr |
Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone |
| title_full_unstemmed |
Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone |
| title_sort |
lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone |
| url |
http://hdl.handle.net/20.500.12110/paper_10242422_v22_n3_p215_Bruttomesso |
| work_keys_str_mv |
AT bruttomessoac lipasecatalyzedpreparationofbiologicallyactiveestersofdehydroepiandrosterone AT tiscorniaa lipasecatalyzedpreparationofbiologicallyactiveestersofdehydroepiandrosterone AT baldessaria lipasecatalyzedpreparationofbiologicallyactiveestersofdehydroepiandrosterone |
| _version_ |
1807317286289145856 |