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Abstract:

Methyl 3-O-acetyl-2-deoxy-α-d-ribofuranoside, 1,3-di-O-acetyl-2-deoxy-α-d-ribofuranose and 1,2,3-tri-O-acetyl-α-d-arabinofuranose were diastereoselectively prepared (de = 100%) from anomeric mixtures of the corresponding 5-acetylated compounds through Candida antarctica B lipase (CAL B)-catalysed alcoholysis. © 2009 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Diastereoselective enzymatic preparation of acetylated pentofuranosides carrying free 5-hydroxyl groups
Autor:Gudiño, E.D.; Iribarren, A.M.; Iglesias, L.E.
Filiación:Universidad Nacional de Quilmes, Roque Sáenz Peña 352-, 1876 Bernal, Provincia de Buenos Aires, Argentina
INGEBI (CONICET)-Vuelta de Obligado 2490-, 1428 Buenos Aires, Argentina
Palabras clave:1,2,3 tri o acetyl alpha dextro arabinofuranose; 1,3 di o acetyl 2 deoxy alpha dextro ribofuranose; carbohydrate derivative; hydroxyl group; lipase B; methyl 3 o acetyl 2 deoxy alpha dextro ribofuranoside; unclassified drug; acetylation; alcoholysis; article; Candida antarctica; diastereoisomer; enzyme mechanism; nonhuman; priority journal; quantum yield; reaction analysis; stereochemistry
Año:2009
Volumen:20
Número:15
Página de inicio:1813
Página de fin:1816
DOI: http://dx.doi.org/10.1016/j.tetasy.2009.07.001
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v20_n15_p1813_Gudino

Referencias:

  • Tanmaya, P., (2002) Chem. Rev., 102, p. 1623
  • Bornsheuer, U., Kazlauskas, R., (2004) Hydrolases in Organic Chemistry, , Wiley, Weinheim Chapter 5, pp 141-152
  • Kadereit, D., Waldmann, H., (2001) Chem. Rev., 101, p. 3367
  • La Ferla, B., (2002) Monatsh. Chem., 133, p. 351
  • Gonçalves, P.L.M., Roberts, S.M., Wan, P.W.H., (2004) Tetrahedron, 60, p. 927
  • Filice, M., Fernández-Lafuente, R., Terreni, M., Guisán, J.M., Palomo, J.M., (2007) J. Mol. Catal. B: Enzym., 49, p. 12
  • Hennen, W.J., Sweers, H.M., Wang, Y.F., Wong, C.H., (1988) J. Org. Chem., 53, p. 4939
  • Fernández-Lorente, G., Palomo, J.M., Cocca, J., Mateo, C., Moro, P., Terreni, M., Fernández-Lafuente, R., Guisán, J.M., (2003) Tetrahedron, 59, p. 5705
  • Chien, T.C., Chern, J.W., (2004) Carbohydr. Res., 339, p. 1215
  • Jun, S.J., Moon, M.S., Lee, S.H., Cheong, C.S., Kim, K.S., (2005) Tetrahedron Lett., 46, p. 5063
  • Antona, N., El-Idrissi, M., Ittobane, N., Nicolosi, G., (2005) Carbohydr. Res., 340, p. 319
  • Prasad, A.K., Kalra, N., Yadav, Y., Kumar, R., Sharma, S.K., Patkar, S., Lange, L., Parmar, V.S., (2007) Chem. Commun., p. 2616
  • Prasad, A.K., Kalra, N., Yadav, Y., Singh, S.K., Sharma, S.K., Patkar, S., Lange, L., Parmar, V.S., (2007) Org. Biomol. Chem., 5, p. 3524
  • Zinni, M.A., Gallo, M., Iglesias, L.E., Iribarren, A.M., (2000) Biotechnol. Lett., 22, p. 361
  • Zinni, M.A., Iglesias, L.E., Iribarren, A.M., (2002) Biotechnol. Lett., 24, p. 979
  • Zinni, M.A., Pontiggia, R., Rodríguez, S.D., Montserrat, J.M., Iglesias, L.E., Iribarren, A.M., (2004) J. Mol. Catal. B: Enzym., 29, p. 129
  • Zinni, M.A., Iglesias, L.E., Iribarren, A.M., (2007) J. Mol. Catal. B: Enzym., 47, p. 86
  • Iñigo, S., Taverna Porro, M., Montserrat, J.M., Iglesias, L.E., Iribarren, A.M., (2005) J. Mol. Catal. B: Enzym., 35, p. 70
  • Taverna Porro, M., Montserrat, J.M., Iribarren, A.M., (2008) Tetrahedron Lett., 49, p. 4642
  • Nicolosi, G., Spatafora, C., Tringali, C., (1999) Tetrahedron: Asymmetry, 10, p. 2891
  • Danieli, B., Luisetti, M., Sampagnaro, G., Carrea, G., Riva, S., (1997) J. Mol. Catal. B: Enzym., 3, p. 193
  • García, J., Díaz-Rodríguez, A., Fernández, S., Sanghvi, Y.S., Ferrero, M., Gotor, V., (2006) J. Org. Chem., 71, pp. 9765-9771
  • Prasad, A.K., Sorensen, M.D., Parmar, V.S., Wengel, J., (1995) Tetrahedron Lett., 36, p. 6163

Citas:

---------- APA ----------
Gudiño, E.D., Iribarren, A.M. & Iglesias, L.E. (2009) . Diastereoselective enzymatic preparation of acetylated pentofuranosides carrying free 5-hydroxyl groups. Tetrahedron Asymmetry, 20(15), 1813-1816.
http://dx.doi.org/10.1016/j.tetasy.2009.07.001
---------- CHICAGO ----------
Gudiño, E.D., Iribarren, A.M., Iglesias, L.E. "Diastereoselective enzymatic preparation of acetylated pentofuranosides carrying free 5-hydroxyl groups" . Tetrahedron Asymmetry 20, no. 15 (2009) : 1813-1816.
http://dx.doi.org/10.1016/j.tetasy.2009.07.001
---------- MLA ----------
Gudiño, E.D., Iribarren, A.M., Iglesias, L.E. "Diastereoselective enzymatic preparation of acetylated pentofuranosides carrying free 5-hydroxyl groups" . Tetrahedron Asymmetry, vol. 20, no. 15, 2009, pp. 1813-1816.
http://dx.doi.org/10.1016/j.tetasy.2009.07.001
---------- VANCOUVER ----------
Gudiño, E.D., Iribarren, A.M., Iglesias, L.E. Diastereoselective enzymatic preparation of acetylated pentofuranosides carrying free 5-hydroxyl groups. Tetrahedron Asymmetry. 2009;20(15):1813-1816.
http://dx.doi.org/10.1016/j.tetasy.2009.07.001