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Abstract:

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.

Registro:

Documento: Artículo
Título:Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone
Autor:Bruttomesso, A.C.; Tiscornia, A.; Baldessari, A.
Filiación:Depto. Quimica Organica y UMYMFOR, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Piso 3, 1428 Buenos Aires, Argentina
Palabras clave: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
Año:2004
Volumen:22
Número:3
Página de inicio:215
Página de fin:220
DOI: http://dx.doi.org/10.1080/10242420410001697070
Título revista:Biocatalysis and Biotransformation
Título revista abreviado:Biocatal. Biotransform.
ISSN:10242422
CODEN:BOBOE
CAS:prasterone, 53-43-0; triacylglycerol lipase, 9001-62-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v22_n3_p215_Bruttomesso

Referencias:

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Citas:

---------- APA ----------
Bruttomesso, A.C., Tiscornia, A. & Baldessari, A. (2004) . Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone. Biocatalysis and Biotransformation, 22(3), 215-220.
http://dx.doi.org/10.1080/10242420410001697070
---------- CHICAGO ----------
Bruttomesso, A.C., Tiscornia, A., Baldessari, A. "Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone" . Biocatalysis and Biotransformation 22, no. 3 (2004) : 215-220.
http://dx.doi.org/10.1080/10242420410001697070
---------- MLA ----------
Bruttomesso, A.C., Tiscornia, A., Baldessari, A. "Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone" . Biocatalysis and Biotransformation, vol. 22, no. 3, 2004, pp. 215-220.
http://dx.doi.org/10.1080/10242420410001697070
---------- VANCOUVER ----------
Bruttomesso, A.C., Tiscornia, A., Baldessari, A. Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone. Biocatal. Biotransform. 2004;22(3):215-220.
http://dx.doi.org/10.1080/10242420410001697070