Navegar

Colección

Datos Estadísticas

Artículo

Zinni, M.A.; Rodríguez, S.D.; Pontiggia, R.M.; Montserrat, J.M.; Iglesias, L.E.; Iribarren, A.M. "Enzymatic alcoholysis of 3′,5′-di-O-acetyl-2′- deoxynucleosides" (2004) Journal of Molecular Catalysis B: Enzymatic. 29(1-6):129-132
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Candida antarctica-B (CAL-B) lipase-catalysed alcoholysis of a set of 3′,5′-di-O-acetyl-2′-deoxynucleosides (1a-e) gave the corresponding 3′-O-acetyl-2′-deoxy-nucleosides (2a-e) in yields ranging from 50 to 96%. The alcohol employed in the biotransformation affected the rate of the enzymatic reaction and the yield of the 3′-O-acetylated product, but in all cases only this regioisomer was formed. The obtained results are in agreement with the regioselectivity displayed by CAL-B lipase in previously reported biotransformations of nucleosides. CAL-B catalysed alcoholysis of 2′,3′,5′-tri-O-acetyl-cytidine and 4-N-acetyl-2′,3′,5′-tri-O-acetylcytidine was also studied, affording with the same regioselectivity the corresponding free 5′-hydroxyl nucleosides. © 2004 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Enzymatic alcoholysis of 3′,5′-di-O-acetyl-2′- deoxynucleosides
Autor:Zinni, M.A.; Rodríguez, S.D.; Pontiggia, R.M.; Montserrat, J.M.; Iglesias, L.E.; Iribarren, A.M.
Filiación:Centro de Estudios e Investigaciones, Universidad Nacional de Quilmes, Roque Sáenz Peña 180, Provincia de Buenos Aires, Argentina
INGEBI (CONICET), Vuelta de Obligado 2490, (1428) Buenos Aires, Argentina
Palabras clave:Deacetylation; Enzymatic alcoholysis; Lipases; Nucleosides; Regioselectivity; Alcohols; Catalysis; Alcoholysis; Biotransformation; Enzymes; 2',3',5' tri o acetylcytidine; 3',5' di o acetyl 2' deoxyadenosine; 3',5' di o acetyl 2' deoxycytidine; 3',5' di o acetyl 2' deoxyguanosine; 3',5' di o acetyl 2' deoxyuridine; 3',5' di o acetylthymidine; 4 n acetyl 2',3',5' tri o acetylcytidine; alcohol derivative; cytidine derivative; hydroxyl group; nucleoside derivative; triacylglycerol lipase; unclassified drug; acetylation; alcoholysis; biotransformation; Candida antarctica; catalysis; conference paper; enzyme activity; fungal strain; isomer; stereochemistry; Candida; Candida antarctica
Año:2004
Volumen:29
Número:1-6
Página de inicio:129
Página de fin:132
DOI: http://dx.doi.org/10.1016/j.molcatb.2003.11.017
Título revista:Journal of Molecular Catalysis B: Enzymatic
Título revista abreviado:J. Mol. Catal. B Enzym.
ISSN:13811177
CODEN:JMCEF
CAS:triacylglycerol lipase, 9001-62-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v29_n1-6_p129_Zinni

Referencias:

  • Ferrero, M., Gotor, V., (2000) Chem. Rev., 100, p. 4319
  • Kadereit, D., Waldmann, H., (2001) Chem. Rev., 101, p. 3367
  • Uemura, A., Nozaki, K., Yamashita, J.I., Yasumoto, M., (1989) Tetrahedron Lett., 30, p. 3819
  • Crout, D.H.G., Dachs, A.M., Glover, S.E., Hutchinson, D.W., (1990) Biocatalysis, 4, p. 177
  • Waldmann, H., Heuser, A., Reidel, A., (1994) Synlett, p. 65
  • Ciuffreda, P., Casati, S., Santaniello, E., (1999) Bioorg. Med. Chem. Lett., 9, p. 1577
  • García, J., Fernández, S., Ferrero, M., Sanghvi, Y.S., Gotor, V., (2002) J. Org. Chem., 67, p. 4513
  • Ciuffreda, P., Casati, S., Santaniello, E., (2000) Tetrahedron, 56, p. 3239
  • Singh, H.K., Cote, G.L., Sikorski, R.S., (1993) Tetrahedron Lett., 34, p. 5201
  • Iglesias, L.E., Zinni, M.A., Gallo, M., Iribarren, A.M., (2000) Biotechnol. Lett., 22, p. 361
  • Roncaglia, D.I., Schmidt, A.M., Iglesias, L.E., Iribarren, A.M., (2001) Biotechnol. Lett., 23, p. 1439
  • Zinni, M.A., Iglesias, L.E., Iribarren, A.M., (2002) Biotechnol. Lett., 24, p. 979
  • Cicero, D.O., Gallo, M., Neuner, P.J., Iribarren, A.M., (2001) Tetrahedron, 57, p. 7613
  • Matzuda, A., Shinozaki, M., Suzuki, M., Watanabe, K., Miyasaka, T., (1986) Synthesis, p. 385
  • Morís, F., Gotor, V., (1993) J. Org. Chem., 58, p. 653
  • Gotor, V., Morís, F., (1992) Synthesis, p. 626
  • Nair, R.V., Salunkhe, M.M., (2000) Synth. Commun., 30, p. 3115

Citas:

---------- APA ----------
Zinni, M.A., Rodríguez, S.D., Pontiggia, R.M., Montserrat, J.M., Iglesias, L.E. & Iribarren, A.M. (2004) . Enzymatic alcoholysis of 3′,5′-di-O-acetyl-2′- deoxynucleosides. Journal of Molecular Catalysis B: Enzymatic, 29(1-6), 129-132.
http://dx.doi.org/10.1016/j.molcatb.2003.11.017
---------- CHICAGO ----------
Zinni, M.A., Rodríguez, S.D., Pontiggia, R.M., Montserrat, J.M., Iglesias, L.E., Iribarren, A.M. "Enzymatic alcoholysis of 3′,5′-di-O-acetyl-2′- deoxynucleosides" . Journal of Molecular Catalysis B: Enzymatic 29, no. 1-6 (2004) : 129-132.
http://dx.doi.org/10.1016/j.molcatb.2003.11.017
---------- MLA ----------
Zinni, M.A., Rodríguez, S.D., Pontiggia, R.M., Montserrat, J.M., Iglesias, L.E., Iribarren, A.M. "Enzymatic alcoholysis of 3′,5′-di-O-acetyl-2′- deoxynucleosides" . Journal of Molecular Catalysis B: Enzymatic, vol. 29, no. 1-6, 2004, pp. 129-132.
http://dx.doi.org/10.1016/j.molcatb.2003.11.017
---------- VANCOUVER ----------
Zinni, M.A., Rodríguez, S.D., Pontiggia, R.M., Montserrat, J.M., Iglesias, L.E., Iribarren, A.M. Enzymatic alcoholysis of 3′,5′-di-O-acetyl-2′- deoxynucleosides. J. Mol. Catal. B Enzym. 2004;29(1-6):129-132.
http://dx.doi.org/10.1016/j.molcatb.2003.11.017