Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF

Green Chemistry

Volumn 11, Issue 6, 2009, Pages 855-86

  Simeó, Yolanda ^a   Sinisterra, José Vicente ^a,b   Alcántara, Andrés R ^a,b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b Industrial Biotransformations Service   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CANDIDA ANTARCTICA;

EID: 67649103762     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b818992g     Document Type: Article

References (40)

1. C. K. Chu, and D. C. Baker, Nucleosides and Nucleotides as Antitumor and Antiviral Agents, Plenum Press, New York, 1993.
2. L. B. Townsend, Chemistry of Nucleosides and Nucleotides, Plenum Press, New York, 1988.
3. S. D. Chamberlain A. R. Moorman L. A. Jones P. de Miranda D. J. Reynolds G. W. Kozalka T. A. Krenitsky Antiviral Chem. Chemother. 1992 3 371.
4. E. K. Hamamura M. Prystasz J. P. H. Verheyden J. G. Moffatt K. Yamaguchi N. Uchida K. Sato A. Nomura O. Shiratori S. Takase K. Katagiri J. Med. Chem. 1976 19 654.
5. L. Colla E. de Clercq R. Busson H. Vanderhaeghe J. Med. Chem. 1983 26 602.
6. L. M. Beauchamp G. F. Orr P. de Miranda T. Burnette T. A. Krenitsky Antiviral Chem. Chemother. 1992 3 157.
7. X. Li Q. Wu D.-S. Lv X.-F. Lin Bioorg. Med. Chem. 2006 14 3377.
8. S. Shimokawa J. Kimura O. Mitsunobu Bull. Chem. Soc. Jpn. 1976 49 3357.
9. D. C. Baker T. H. Haskell S. R. Putt B. J. Sloan J. Med. Chem. 1979 22 273.
10. L. A. Condezo, J. Fernández-Lucas, C. A. García-Burgos, A. R. Alcántara, and J. V. Sinisterra, Biocatalysis in the Pharmaceutical and Biotechnology Industries, ed. R. N. Patel, Taylor & Francis, CRC press, New York, 2006.
11. M. Ferrero V. Gotor Chem. Rev. 2000 100 4319.
12. J. García S. Fernández M. Ferrero Y. S. Sanghvi V. Gotor J. Org. Chem. 2002 67 4513.
13. M. A. Zinni L. E. Iglesias A. M. Iribarren J. Mol. Catal. B: Enzym. 2007 47 86.
14. K. Faber, Biotransformations in Organic Chemistry, Springer-Verlag, Berlin-Heidelberg, 2000.
15. Information provided by Penn Specialty Chemicals Inc., and also available from D. Aul and B. Comanita, Manufacturing Chemist, May 2007, 33.
16. D. F. Aycock Org. Process Res. Dev. 2007 11 156.
17. S. Mitra S. R. Gurrala R. S. Coleman J. Org. Chem 2007 72 8724.
18. S. Nuwa, S. Handa, S. Miki, U.S. Patent, 20050043544.
19. J. Miller, J. Penney, U.S. Patent, 20050137402.
20. S. Krishnan S. Schreiber Org. Lett. 2004 6 4021.
21. D. Spring S. Krishnan S. Schreiber J. Am. Chem. Soc. 2000 122 5656.
22. K. Nakamura M. Kinoshita A. Ohno Tetrahedron 1994 50 44681.
23. F. Morís V. Gotor J. Org. Chem. 1993 58 653.
24. J. García S. Fernández M. Ferrero Y. S. Sanghvi V. Gotor Tetrahedron Lett. 2004 45 1709.
25. F. Morís V. Gotor Tetrahedron 1994 50 6927.
26. X.-F. Sun N. Wang Q. Wu X.-F. Lin Biotechnol. Lett. 2004 26 1019.
27. M. D. Romero L. Calvo C. Alba A. Daneshfar H. S. Ghaziaskar Enzyme Microb. Technol. 2005 37 42.
28. J. Xu J. Zhu T. Kawamoto T. Atsuo Y. Hu Chin. J. Biotechnol. 1997 13 263.
29. Y. Mei L. Miller W. Gao R. A. Gross Biomacromolecules 2003 4 70.
30. P. Hudson R. K. Eppler D. S. Clark Curr. Opin. Biotechnol. 2005 16 637.
31. R. Chenevert N. Pelchat F. Jacques Curr. Org. Chem. 2006 10 1067.
32. P. Hoyos M. Fernandez J. V. Sinisterra A. R. Alcántara J. Org. Chem. 2006 71 7632.
33. A. Uemura K. Nozaki J.-I. Yamashita M. Yasumoto Tetrahedron Lett. 1989 30 3817.
34. Y. Tokiwa, H. Fan, T. Raku, and M. Kitagawa, Biocatalysis in Polymer Science, ed. R. A. Gross, and H. N. Cheng, ACS Symp. Ser. Nr. 840, Washington DC, 2003.
35. M. Kitagawa H. Fan T. Raku R. Kurane Y. Tokiwa Biotechnol. Lett. 2000 22 883.
36. M. Grotli M. Douglas R. Eritja B. S. Sproat Tetrahedron 1998 54 5899.
37. K.-H. Altmann P. Martin N. M. Dean B. P. Monia Nucleosides Nucleotides 1997 16 917.
38. T. Nakaoki Y. Mei L. M. Miller A. Kumar B. Kalra M. E. Miller O. Kirk M. Christensen R. A. Gross Ind. Biotechnol. 2005 1 126.
39. PLU = propyl laurate units, defined as the amount of catalyst producing 1 μmol of propyl laurate per minute, at 60 °C, Novozymes analytical method F-9600369.
40. Information from www.Sigma-Aldrich.com.