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Sabaini, M.B.; Zinni, M.A.; Mohorčič, M.; Friedrich, J.; Iribarren, A.M.; Iglesias, L.E. "Enzymatic regioselective and complete deacetylation of two arabinonucleosides" (2010) Journal of Molecular Catalysis B: Enzymatic. 62(3-4):225-229
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Abstract:

Candida antarctica lipase B (CAL-B)-catalysed regioselective deacetylation of 2′,3′,5′-tri- O-acetyl-1-β- d-arabinofuranosyluracil (1) and 2′,3′,5′-tri- O-acetyl-9-β- d-arabinofuranosyladenine (2) was studied. The choice of the reaction medium allowed the regioselective formation of products bearing different degree of acetylation: in isopropanol, CAL-B catalysed the formation of the corresponding 2′- O-acetylated arabinonucleosides, while hydrolyses afforded the 2′,3′-di- O-acetylated products. In particular, the procedure herein described allows a simple and efficient preparation of the reported vidarabine prodrug 2′,3′-di- O-acetyl-9-β- d-arabinofuranosyladenine, avoiding the utilisation of protective groups. Moreover, to achieve full deacetylation of the assayed substrates, a set of commercial hydrolases and fungal keratinases from Doratomyces microsporus (DMK) and Paecilomyces marquandii (PMK) were tested. While only PMK and DMK catalysed the quantitative complete deacetylation of 1, DMK accomplished full deacetylation of 2 in shorter time than the other assayed enzymes. © 2009 Elsevier B.V.

Registro:

Documento: Artículo
Título:Enzymatic regioselective and complete deacetylation of two arabinonucleosides
Autor:Sabaini, M.B.; Zinni, M.A.; Mohorčič, M.; Friedrich, J.; Iribarren, A.M.; Iglesias, L.E.
Filiación:Department of Science and Technology, Universidad Nacional de Quilmes, Roque Sáenz Peña 352, 1876 Bernal, Provincia de Buenos Aires, Argentina
Department of Biotechnology, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia
INGEBI (CONICET), Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina
Palabras clave:Keratinase; Lipase; Nucleosides; Prodrugs; Regioselectivity; Candida antarctica lipase B; Deacetylation; Degree of acetylation; Hydrolases; Iso-propanols; Keratinase; Nucleosides; Paecilomyces marquandii; Prodrugs; Protective group; Reaction medium; Regio-selective; Regioselective deacetylation; Biomolecules; Catalysis; Regioselectivity; Acetylation; 2 propanol; 2',3',5' tri o acetyl 1 beta dextro arabinofuranosyluracil; 2',3',5' tri o acetyl 9 beta dextro arabinofuranosyladenine; arabinonucleoside; fungal enzyme; hydrolase; keratinase; lipase B; unclassified drug; vidarabine; article; Candida antarctica; catalysis; controlled study; deacetylation; Doratomyces microsporus; drug structure; enzyme assay; enzyme mechanism; enzyme substrate; fungus; nonhuman; paecilomyces marquandii; protein hydrolysis; quantitative analysis; reaction time; Candida antarctica; Doratomyces microsporus; Paecilomyces marquandii
Año:2010
Volumen:62
Número:3-4
Página de inicio:225
Página de fin:229
DOI: http://dx.doi.org/10.1016/j.molcatb.2009.10.011
Título revista:Journal of Molecular Catalysis B: Enzymatic
Título revista abreviado:J. Mol. Catal. B Enzym.
ISSN:13811177
CODEN:JMCEF
CAS:2 propanol, 67-63-0; hydrolase, 9027-41-2; keratinase, 37288-91-8, 37341-53-0, 9025-41-6; vidarabine, 2006-02-2, 5536-17-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v62_n3-4_p225_Sabaini

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Citas:

---------- APA ----------
Sabaini, M.B., Zinni, M.A., Mohorčič, M., Friedrich, J., Iribarren, A.M. & Iglesias, L.E. (2010) . Enzymatic regioselective and complete deacetylation of two arabinonucleosides. Journal of Molecular Catalysis B: Enzymatic, 62(3-4), 225-229.
http://dx.doi.org/10.1016/j.molcatb.2009.10.011
---------- CHICAGO ----------
Sabaini, M.B., Zinni, M.A., Mohorčič, M., Friedrich, J., Iribarren, A.M., Iglesias, L.E. "Enzymatic regioselective and complete deacetylation of two arabinonucleosides" . Journal of Molecular Catalysis B: Enzymatic 62, no. 3-4 (2010) : 225-229.
http://dx.doi.org/10.1016/j.molcatb.2009.10.011
---------- MLA ----------
Sabaini, M.B., Zinni, M.A., Mohorčič, M., Friedrich, J., Iribarren, A.M., Iglesias, L.E. "Enzymatic regioselective and complete deacetylation of two arabinonucleosides" . Journal of Molecular Catalysis B: Enzymatic, vol. 62, no. 3-4, 2010, pp. 225-229.
http://dx.doi.org/10.1016/j.molcatb.2009.10.011
---------- VANCOUVER ----------
Sabaini, M.B., Zinni, M.A., Mohorčič, M., Friedrich, J., Iribarren, A.M., Iglesias, L.E. Enzymatic regioselective and complete deacetylation of two arabinonucleosides. J. Mol. Catal. B Enzym. 2010;62(3-4):225-229.
http://dx.doi.org/10.1016/j.molcatb.2009.10.011