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Abstract:

In this article, we describe the application of lipases in acylation and alcoholysis reactions on steroids and nucleosides. In the field of steroids, a variety of acetyl and fatty acid derivatives of androstanes, pregnanes, and cholestanes have been prepared through lipase-catalyzed acylation and alcoholysis reactions taking advantage of the high regio- and stereoselectivity of these enzymes. The substrates as well as the products show a high degree of biological activity as neurosteroids, hormones, and glucocorticoids. The regioselective preparation of diacylated nucleosides by means of an enzymatic alcoholysis allowed the synthesis of nucleosides prodrugs or modified nucleosides. The quantitative full deacylation and dealkoxycarbonylation of nucleosides and steroids is a mild synthetic method for the deprotection of these labile compounds. Some of the reported steroid and nucleoside products are novel, and it is not possible to obtain them satisfactorily by following traditional synthetic procedures. The advantages presented by this methodology, such as selectivity, mild reaction conditions, and low environmental impact, make the lipases an important tool in the application of the principles of Green Chemistry, offering a convenient way to prepare derivatives of natural compounds with a great potential in the pharmaceutical industry. © 2012 Springer Science+Business Media New York.

Registro:

Documento: Artículo
Título:Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides
Autor:Baldessari, A.; Iglesias, L.E.
Filiación:Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Universidad de Buenos Aires, Buenos Aires, Argentina
Laboratorio de Biotransformaciones, Departamento de Ciencia y Tecnología, Universidad Nacional de Quilmes, Bernal, Buenos Aires, Argentina
Palabras clave:Acylation and alcoholysis reactions; Green Chemistry; Lipases; Nucleosides; Steroids; androstane derivative; biological product; cholestane derivative; fatty acid; fungal protein; lipase B, Candida antarctica; nucleoside; pregnane derivative; prodrug; triacylglycerol lipase; acylation; article; biocatalysis; Candida; chemistry; green chemistry; stereoisomerism; synthesis; Acylation; Androstanes; Biocatalysis; Biological Agents; Candida; Cholestanes; Fatty Acids; Fungal Proteins; Green Chemistry Technology; Lipase; Nucleosides; Pregnanes; Prodrugs; Stereoisomerism
Año:2012
Volumen:861
Página de inicio:457
Página de fin:469
DOI: http://dx.doi.org/10.1007/978-1-61779-600-5_26
Título revista:Methods in Molecular Biology
Título revista abreviado:Methods Mol. Biol.
ISSN:10643745
CAS:triacylglycerol lipase, 9001-62-1; Androstanes; Biological Agents; Cholestanes; Fatty Acids; Fungal Proteins; Lipase, 3.1.1.3; Nucleosides; Pregnanes; Prodrugs; lipase B, Candida antarctica, 3.1.1.-
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10643745_v861_n_p457_Baldessari

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Citas:

---------- APA ----------
Baldessari, A. & Iglesias, L.E. (2012) . Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides. Methods in Molecular Biology, 861, 457-469.
http://dx.doi.org/10.1007/978-1-61779-600-5_26
---------- CHICAGO ----------
Baldessari, A., Iglesias, L.E. "Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides" . Methods in Molecular Biology 861 (2012) : 457-469.
http://dx.doi.org/10.1007/978-1-61779-600-5_26
---------- MLA ----------
Baldessari, A., Iglesias, L.E. "Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides" . Methods in Molecular Biology, vol. 861, 2012, pp. 457-469.
http://dx.doi.org/10.1007/978-1-61779-600-5_26
---------- VANCOUVER ----------
Baldessari, A., Iglesias, L.E. Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides. Methods Mol. Biol. 2012;861:457-469.
http://dx.doi.org/10.1007/978-1-61779-600-5_26