A versatile synthesis of 5'-fenctionalized nucleosides through regioselective enzymatic hydrolysis of their peracetylated precursors

European Journal of Organic Chemistry

Volumn , Issue 12, 2009, Pages 1967-1975

  Bavaro, Teodora ^a,b   Rocchietti, Silvia ^a,b   Ubiali, D ^a   Filice, Marco ^a   Terreni, Marco ^a   Pregnolato, Massimo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b Innovate Biotechnology srl   (Italy)

Author keywords

Enzymes; Immobilization; Lipases; Nucleosides; Regioselectivity

Indexed keywords

EID: 63849119951     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801096     Document Type: Article

References (31)

1. H. Vorbruggen, C. Ruh-Pohlenz, Synthesis of Nucleosides in Organic Reactions, Wiley, New York, 2000.
2. H. Vorbruggen, C. Ruh-Pohlenz, Handbook of Nucleosides Synthesis, Wiley, New York, 2001.
3. C. M. Galmarini, J. R. Mackey, C. Dumontet, Lancet Oncol. 2002, 3, 415-424.'
4. P. Herdewijn, Current Protocols in Nucleic Acid Chemistry, John Wiley & Sons, New York, 2007, pp. 14.0.1-14.0.6.
5. M. Ferrero, V. Gotor, Chem. Rev. 2000, 100, 4319-4347.
6. C, H. Wong, G. M. Whitesides, Enzymes in Synthetic Organic Chemistry Pergamon, Oxford, 1994.
7. A. K. Prasad, S. Trikha, V. S. Parmar, Bioorg. Chem. 1999, 27, 135-154.
8. R. D. Schmid, R. Verger, Angew. Chem, Int. Ed. 1998, 37, 1609-1633.
9. B. La Ferla, Monatsh. Chem. 2002, 133, 351-368.
10. a) A. Uemura, K. Nozaki, J. Yamashita, M. Yasumoto, Tetrahedron Lett. 1989, 30, 3819-3820;
11. H. K. Singh, G. L. Cote, R. S. Sikorski, Tetrahedron Lett. 1993, 34, 5201-5204;
12. A. Zinni, A. Schmidt, M. Gallo, L. Iglesias, A. Iribarren, Molecules 2000, 5, 533-534;
13. D.I. Roncaglia, A.M. Schmidt, L. E. Iglesias, A. M. Iribarren, Biotechnol. Lett. 2001, 23, 1439-1443;
14. M. A. Zinni, S. D. Rodríguez, R. M. Pontiggia, J. M. Montserrat, L. F.. Iglesias, A. M. Iribarren, J. Mol. Catal. B Enzym. 2004, 29, 129-132.
15. S. Rocchietti, M. Terreni, M. Pregnolato, PCX Int. Appl. WO03057894, EP1466004A1, AU2003235812A1; Chem. Abstr. 2003, 139, 116337.
16. A. Bastida, P. Sabuquillo, P. Armisen, R. Femàndez-Lafuente, J. Huguet, J. M. Guisàn, Biotechnol. Bioeng. 1998, 58, 486-493.
17. D. B. Longley, D. P. Harkin, P. G. Johnston, Nat. Rev. Cancer 2003, 3, 330-338.
18. a) H. Jyonouchi, J. Nutr. 1994, 124, 138S-143S;
19. C. T. Van Buren, A. D. Kulkarni, F. B. Rudolph, J. Nutr. 1994, 124, 160S-164S.
20. F. Moris, V. Gotor, Tetrahedron 1993, 49, 10089-10098.
21. F. Barre-Sinoussi, J. C. Chermann, F. Rey, M. T. Nugeyre, S. Chamaret, I Gruest, C. Dauguet, C. Axler-Blin. F. Vezinet- Brun, C. Rouzioux, W. Rozenbaum. L. Montagnier. Science 1983, 220, 868-871.
22. a) J. Y. N. Lau, R. C. Tarn, T. J. Liang, Z. Hong, Hepatology 2002, 55, 1002-1009;
23. R. T. Chung, M. Gale Jr.,S. J. Polyak, S. M. Lemon, T. J. Liang, J. H. Hoofnagle, Hepatology 2008, 47, 306-320.
24. L, Cao, Curr. Opin. Chem. Biol. 2005, 9, 217-226.
25. L. Hein, P. Draser, J. Beranek, Nucleic Acids Res. 1976, 3, 1125-1137.
26. F. Sajtos, J. Hajkò, K. E. Kövér, A. Lipták, Carbohydr. Res. 2001, 334, 253-259.
27. S. Rocchietti, D. Ubiali. M. Terreni, A.M. Albertini. R. Fernandez-Lafuente. J. M. Guisan, M. Pregnolato. Biomacromolecules 2004, 5, 2195-2200.
28. M. Yoshikawa, T. Kato. T. Takenishi, Bull. Chem. Soc. Jpn. 1969, 42, 3505-3508.
29. C. Mateo, J. M. Palomo, G. Fernandez-Lorente, J. M. Guisan, R. Fernandez-Lafuente, Enzyme Microb. Technol. 2007, 40, 1451-1463.
30. D. Ubiali, S. Rocchietti, F. Scaramozzino, M. Terreni, A.M. Albertini, R. Fernandez-Lafuente, J. M. Guisan, M. Pregnolato, Adv. Synth. Catal. 2004, 346, 1361-1366.
31. V. Gotor, F. Moris, Synthesis 1992, 7, 626-628.