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Abstract:

Unlike the preparation of other purine nucleosides, transglycosylation from a pyrimidine nucleoside and guanine is difficult because of the low solubility of this base. Thus, another strategy, based on the coupled action of two whole cell biocatalyzed reactions, transglycosylation and deamination, was used. Enterobacter gergoviae and Arthrobacter oxydans were employed to synthesize 9-β-d-arabinofuranosylguanine (AraG), an efficient anti leukemic drug. © 2009 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of 9-β-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts
Autor:Médici, R.; Iribarren, A.M.; Lewkowicz, E.S.
Filiación:Biotransformations Laboratory, Universidad Nacional de Quilmes. R.S. Peña 352, 1876 Bernal Buenos Aires, Argentina
INGEBI, CONICET, Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina
Palabras clave:Adenosine deaminase; Arabinofuranosylguanine; Nucleoside phosphorylases; Whole cell biocatalysts; guanine; guanine arabinoside; purine nucleoside; pyrimidine nucleoside; Arthrobacter; article; biocatalyst; catalysis; deamination; drug structure; drug synthesis; Enterobacter; glycosylation; high performance liquid chromatography; nonhuman; Antineoplastic Agents; Arabinonucleosides; Arthrobacter; Catalysis; Cell Line; Cell Line, Tumor; Chemistry, Pharmaceutical; Drug Design; Drug Screening Assays, Antitumor; Enterobacter; Glycosylation; Humans; Leukemia; Models, Chemical; Arthrobacter oxydans; Enterobacter gergoviae
Año:2009
Volumen:19
Número:15
Página de inicio:4210
Página de fin:4212
DOI: http://dx.doi.org/10.1016/j.bmcl.2009.05.106
Título revista:Bioorganic and Medicinal Chemistry Letters
Título revista abreviado:Bioorg. Med. Chem. Lett.
ISSN:0960894X
CODEN:BMCLE
CAS:guanine, 69257-39-2, 73-40-5; guanine arabinoside, 38819-10-2; 9-arabinofuranosylguanine, 38819-10-2; Antineoplastic Agents; Arabinonucleosides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0960894X_v19_n15_p4210_Medici

Referencias:

  • Herrström Sjöberg, A., Wang, L., Eriksson, S., (2001) Antimicrob. Agents Chemother., 45, p. 739
  • Buie, L.B., Epstein, S.S., Lindley, C.M., (2007) Clin. Ther., 29, p. 1887
  • Lee, W.W., Martínez, A.P., Goodman, L., Henry, D.W., (1972) J. Org. Chem., 37, p. 2923
  • Yu, X.J., Li, G.X., Qi, X.X., Deng, Y.Q., (2005) Bioorg. Med. Chem. Lett., 15, p. 683
  • Utagawa, T., (1999) J. Mol. Catal. B: Enzym., 6, p. 215
  • Lewkowicz, E., Iribarren, A., (2006) Curr. Org. Chem., 10, p. 1197
  • Mikami, Y., Matsumoto, S., Hayashi, Y., Sato, T., (2005), US Patent 0037470; Yokozeki, K., Tsuji, T., (2000) J. Mol. Catal. B: Enzym., 10, p. 207
  • Tonon, G., Capra, E., Orsini, G., Zuffi, G., (2004), US Patent 0142438; Ubiali, D., Rocchietti, S., Scaramozzino, F., Terreni, M., Albertini, A.M., Fernández-Lafuente, R., Guisán, J.M., Pregnolato, M., (2004) Adv. Synth. Catal., 346, p. 1361
  • Okuyama, K., Shibuya, S., Hamamoto, T., Noguchi, T., (2003) Biosci., Biotechnol., Biochem., 67, p. 989
  • Brakta, M., Murthy, D., Ellis, L., Phadtare, S., (2002) Bioorg. Med. Chem. Lett., 12, p. 1489
  • Kawashima, E., Terui, Y.S., Kodama, R., Yokozeki, K., (2006) Tetrahedron Lett., 47, p. 3161
  • Grupta, M., Nair, V., (2005) Tetrahedron Lett., 46, p. 1165
  • Rogert, M.C., Trelles, J.A., Porro, S., Lewkowicz, E.S., Iribarren, A.M., (2002) Biocatal. Biotransform., 20, p. 347
  • Médici, R., Lewkowicz, E.S., Iribarren, A.M., (2008) FEMS Microbiol. Lett., 289, p. 20
  • Médici, R., Lewkowicz, E.S., Iribarren, A.M., (2006) J. Mol. Catal. B: Enzym., 39, p. 40

Citas:

---------- APA ----------
Médici, R., Iribarren, A.M. & Lewkowicz, E.S. (2009) . Synthesis of 9-β-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts. Bioorganic and Medicinal Chemistry Letters, 19(15), 4210-4212.
http://dx.doi.org/10.1016/j.bmcl.2009.05.106
---------- CHICAGO ----------
Médici, R., Iribarren, A.M., Lewkowicz, E.S. "Synthesis of 9-β-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts" . Bioorganic and Medicinal Chemistry Letters 19, no. 15 (2009) : 4210-4212.
http://dx.doi.org/10.1016/j.bmcl.2009.05.106
---------- MLA ----------
Médici, R., Iribarren, A.M., Lewkowicz, E.S. "Synthesis of 9-β-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts" . Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 15, 2009, pp. 4210-4212.
http://dx.doi.org/10.1016/j.bmcl.2009.05.106
---------- VANCOUVER ----------
Médici, R., Iribarren, A.M., Lewkowicz, E.S. Synthesis of 9-β-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts. Bioorg. Med. Chem. Lett. 2009;19(15):4210-4212.
http://dx.doi.org/10.1016/j.bmcl.2009.05.106