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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

Referencias:

  • Anastas, P.T., Warner, J.C., (1998) Green Chemistry: Theory and Practice, , Oxford University Press, New York
  • Baldessari, A., (2004) Enzimas, un Caminos Hacia Reacciones Más Limpias, , La Química Verde en Latinoamérica, Green Chemistry Series N̊ 11. Editorial Universidad de Córdoba, Córdoba
  • Gotor, V., Alfonso, I., García Urdiales, E., (2008) Asymmetric Organic Synthesis with Enzymes, , Wiley -VCH, Weinheim
  • Bommarius, A.S., Riebel, B.R., (2004) Biocatalysis, Fundamentals and Applications, , Wiley -VCH, Weinheim
  • Carrea, G., Riva, S., (2008) Organic Synthesis with Enzymes in non-Aqueous Media, , Wiley -VCH, Weinheim
  • Silva, M.M.C., Riva, S., Sa E Melo, M.L., Regioselective enzymatic acylation of vicinal diols of steroids (2005) Tetrahedron, 61 (12), pp. 3065-3073. , DOI 10.1016/j.tet.2005.01.104
  • Cruz Silva, M.M., Riva, S., Sa E Melo, M.L., Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids (2004) Tetrahedron Asymmetry, 15 (7), pp. 1173-1179. , DOI 10.1016/j.tetasy.2004.02.010, PII S0957416604001387
  • Ferrero, M., Gotor, V., (2000) Stereoselective Biocatalysis., , Marcel Dekker, New York
  • Baldessari, A., Maier, M.S., Gros, E.G., Enzymatic deacteylation of steroids bearing labile functions (1995) Tetrahedron. Lett., 36, pp. 4349-4352
  • Baldessari, A., Bruttomeso, A.C., Gros, E.G., Lipase-catalysed regioselective deacetylation of androstane derivatives (1996) Helv. Chim. Acta., 79, pp. 999-1004
  • Bruttomesso, A.C., Baldessari, A., Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution (2004) Journal of Molecular Catalysis B: Enzymatic, 29 (1-6), pp. 149-153. , DOI 10.1016/j.molcatb.2003.10.011, PII S1381117704000499
  • Bruttomesso, A.C., Tiscornia, A., Baldessari, A., Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone (2004) Biocatalysis and Biotransformation, 22 (3), pp. 215-220. , DOI 10.1080/10242420410001697070
  • Rustoy, E.M., Ruiz Arias, I.E., Baldessari, A., (2005) Regioselective Enzymatic Synthesis of Estradiol 17-Fatty Acid Esters, pp. 75-88. , ARKIVOC xii
  • Quintana, P.G., Baldessari, A., Lipasecatalyzed regioseletive preparation of fatty acid esters of hydrocortisone (2009) Steroids, 74, pp. 1007-1014
  • Monsalve, L.N., An effi cient enzymatic preparation of 20-pregnanes succinates: Chemoenzymatic synthesis of 20 b -hemisuccinyloxy- 5 a H-pregnan-3-one (2008) Tetrahedron, 64, pp. 1721-1730
  • Cihlar, T., Ray, A.S., Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine (2010) Antiviral Res., 85, pp. 39-58
  • Galmarini, C.M., Mackey, J.R., Dumontet, C., Nucleoside analogues and nucleobases in cancer treatment (2002) Lancet Oncology, 3 (7), pp. 415-424. , DOI 10.1016/S1470-2045(02)00788-X
  • Ferrero, M., Gotor, V., Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides (2000) Chemical Reviews, 100 (12), pp. 4319-4347. , DOI 10.1021/cr000446y
  • Li, N., Smith, T.J., Zong, M.H., Biocatalytic transformation of nucleoside derivatives (2010) Biotechnol. Adv., 28, pp. 348-366
  • Zinni, M.A., Iglesias, L.E., Iribarren, A.M., Preparation of potential 3-deazauridine and 6-azauridine prodrugs through an enzymatic alcoholysis (2007) Journal of Molecular Catalysis B: Enzymatic, 47 (1-2), pp. 86-90. , DOI 10.1016/j.molcatb.2007.04.005, PII S1381117707000860
  • Zinni, M.A., Enzymatic alcoholysis of 3 ¢ ,5 ¢ -di- O -acetyl-2 ¢ -deoxynucleosides (2004) J. Mol. Catal. B Enzym., 29, pp. 129-132
  • Zinni, M.A., Iglesias, L.E., Iribarren, A.M., Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis (2002) Biotechnology Letters, 24 (12), pp. 979-983. , DOI 10.1023/A:1015648508146
  • Iglesias, L.E., Zinni, M.A., Gallo, M., Iribarren, A.M., Complete and regioselective deacetylation of peracetylated uridines using a lipase (2000) Biotechnology Letters, 22 (5), pp. 361-365. , DOI 10.1023/A:1005620617554
  • Roncaglia, D.I., Schmidt, A.M., Iglesias, L.E., Iribarren, A.M., A simple and efficient enzymatic procedure for the deprotection of two base labile chlorinated purine ribosides (2001) Biotechnology Letters, 23 (17), pp. 1439-1443. , DOI 10.1023/A:1011615224704
  • Capello, M., Imanishi, L., Iglesias, L.E., Iribarren, A.M., Two new dialkoxycarbonylated nucleosides obtained through a regioselective enzymatic alcoholysis (2007) Biotechnology Letters, 29 (8), pp. 1217-1220. , DOI 10.1007/s10529-007-9374-x
  • Capello, M., Gonzalez, M., Rodriguez, S.D., Iglesias, L.E., Iribarren, A.M., A mild and quantitative procedure for the removal of nucleoside alkoxycarbonyl groups using pig liver esterase or Candida antarctica B lipase (2005) Journal of Molecular Catalysis B: Enzymatic, 36 (1-6), pp. 36-39. , DOI 10.1016/j.molcatb.2005.08.001, PII S1381117705001256
  • Baldessari, A., Mangone, C.P., One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals (2001) Journal of Molecular Catalysis - B Enzymatic, 11 (4-6), pp. 335-341. , DOI 10.1016/S1381-1177(00)00018-7, PII S1381117700000187

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