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Abstract:

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.

Registro:

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

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Citas:

---------- APA ----------
Bruttomesso, A.C. & Baldessari, A. (2004) . Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution. Journal of Molecular Catalysis B: Enzymatic, 29(1-6), 149-153.
http://dx.doi.org/10.1016/j.molcatb.2003.10.011
---------- CHICAGO ----------
Bruttomesso, A.C., Baldessari, A. "Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution" . Journal of Molecular Catalysis B: Enzymatic 29, no. 1-6 (2004) : 149-153.
http://dx.doi.org/10.1016/j.molcatb.2003.10.011
---------- MLA ----------
Bruttomesso, A.C., Baldessari, A. "Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution" . Journal of Molecular Catalysis B: Enzymatic, vol. 29, no. 1-6, 2004, pp. 149-153.
http://dx.doi.org/10.1016/j.molcatb.2003.10.011
---------- VANCOUVER ----------
Bruttomesso, A.C., Baldessari, A. Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution. J. Mol. Catal. B Enzym. 2004;29(1-6):149-153.
http://dx.doi.org/10.1016/j.molcatb.2003.10.011