A series of acetoxy derivatives of androstane and pregnane was deacetylated in organic solvents by microbial lipases. The best results were obtained with lipase from Candida antarctica (CAL B), Candida rugosa (CRL) and Pseudomonas sp. (PSL). In some derivatives, CAL B and CRL showed a regioselective behaviour towards the removal of the 3β- or 16α/16β-acetyl group. The results of the enzymatic deacetylation of pregnanes and androstanes substituted by various groups containing an sp2-hybridised C-atom in ring D could suggest that CAL B activity seems to be conditioned by the occurrence of a polar carbon double bond in this part of the steroid skeleton. Ten new steroid derivatives were obtained through this approach. © 2004 Elsevier B.V. All rights reserved.
Documento: | Artículo |
Título: | Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution |
Autor: | Bruttomesso, A.C.; Baldessari, A. |
Filiación: | Depto. de Quim. Organ. and UMYMFOR, Fac. de Ciencias Exactas Y Naturales, Ciudad Universitaria, 1428, Buenos Aires, Argentina |
Palabras clave: | Androstane; Lipase-catalysed deacetylation; Pregnane; Acetylation; Carbon; Catalysis; Derivatives; Organic solvents; Substitution reactions; Androstane; Pregnane; Enzymes; acetic acid derivative; bacterial enzyme; carbon; organic solvent; prasterone; pregnane derivative; steroid; triacylglycerol lipase; atom; Candida antarctica; Candida rugosa; catalysis; chemical bond; conference paper; deacetylation; hybridization; microorganism; Pseudomonas; stereochemistry; Candida; Candida antarctica; Candida rugosa; Pseudomonas; Pseudomonas sp. |
Año: | 2004 |
Volumen: | 29 |
Número: | 1-6 |
Página de inicio: | 149 |
Página de fin: | 153 |
DOI: | http://dx.doi.org/10.1016/j.molcatb.2003.10.011 |
Título revista: | Journal of Molecular Catalysis B: Enzymatic |
Título revista abreviado: | J. Mol. Catal. B Enzym. |
ISSN: | 13811177 |
CODEN: | JMCEF |
CAS: | carbon, 7440-44-0; prasterone, 53-43-0; triacylglycerol lipase, 9001-62-1 |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v29_n1-6_p149_Bruttomesso |