Abstract:
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.
Registro:
Documento: |
Artículo
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Título: | Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
Autor: | Quintana, P.G.; Baldessari, A. |
Filiación: | Laboratorio de Biocatálisis, Departamento de Química Orgánica, UMYMFOR, Pabellón 2, C1428EGA Buenos Aires, Argentina
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Palabras clave: | 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; Esterification; Fatty Acids; Hydrocortisone; Lipase; Candida antarctica |
Año: | 2009
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Volumen: | 74
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Número: | 13-14
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Página de inicio: | 1007
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Página de fin: | 1014
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DOI: |
http://dx.doi.org/10.1016/j.steroids.2009.07.010 |
Título revista: | Steroids
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Título revista abreviado: | Steroids
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ISSN: | 0039128X
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CODEN: | STEDA
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CAS: | triacylglycerol lipase, 9001-62-1; Fatty Acids; Hydrocortisone, 50-23-7; Lipase, 3.1.1.3
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v74_n13-14_p1007_Quintana |
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Citas:
---------- APA ----------
Quintana, P.G. & Baldessari, A.
(2009)
. Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone. Steroids, 74(13-14), 1007-1014.
http://dx.doi.org/10.1016/j.steroids.2009.07.010---------- CHICAGO ----------
Quintana, P.G., Baldessari, A.
"Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone"
. Steroids 74, no. 13-14
(2009) : 1007-1014.
http://dx.doi.org/10.1016/j.steroids.2009.07.010---------- MLA ----------
Quintana, P.G., Baldessari, A.
"Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone"
. Steroids, vol. 74, no. 13-14, 2009, pp. 1007-1014.
http://dx.doi.org/10.1016/j.steroids.2009.07.010---------- VANCOUVER ----------
Quintana, P.G., Baldessari, A. Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone. Steroids. 2009;74(13-14):1007-1014.
http://dx.doi.org/10.1016/j.steroids.2009.07.010