Biocatalytic synthesis of valaciclovir using commercial enzymes

Tetrahedron Letters

Volumn 52, Issue 2, 2011, Pages 215-218

  McClean, Kathleen ^a   Preston, Christopher ^b   Spence, David ^b   Sutton, Peter W ^a   Whittall, John ^a  

^a Heath Business and Technology Park   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; SUBTILISIN; VALACICLOVIR;

ARTICLE; BIOCATALYSIS; DRUG HYDROLYSIS; DRUG SYNTHESIS; DRUG TRANSFORMATION; TRANSESTERIFICATION;

EID: 78649988260     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.161     Document Type: Article

References (28)

1. X.S. Puente, and C. López-Otin J. Biol. Chem. 270 1995 12926 12932
2. Beauchamp, L. M. U.S. Patent 4957,924, 1990; Chem. Abstr. 1990, 112, 112,048.
3. Minimising the Risk of Transmitting Animal Spongiform Encephalopathy Agents via Human and Veterinary Medicinal Products, In European Pharmacopoeia 6.0, 2010, Chapter 5.2.8.
4. M. Wittrup Larsen, D.F. Zielinska, M. Martinelle, A. Hidalgo, L. Juhl Jensen, U.T. Bornscheuer, and K. Hult ChemBioChem 11 2010 796 801
5. I. Kim, X. Song, B.S. Vig, S. Mittal, H.-C. Shin, P.J. Lorenzi, and G.L. Amidon Mol. Pharmacol. 1 2004 117 127
6. Microbes were chosen which have documented hydrolase activity or have been isolated from environments where hydrolase activities might be expected to be used to degrade contaminants/xenobiotics. Additional criteria that were imposed on strain selection were availability, pathogenicity, ease of culture and intellectual property issues.
7. S.R. Bhandya, and D. Soundar Indian J. Chem. 46B 2007 2026 2044
8. L. Kenchaiah, and D. Soundar J. Biotechnol. 117 2005 49 56
9. Using the best enzyme hits from the hydrolysis screen, conditions that were attempted included the use of neat organic solvent, solvent/aqueous buffer or aqueous buffer alone at both low and high pH. Using conditions described in the following references, treatment of l-valine or l-phenylalanine with ethanol in the presence of Subtilisin A also failed to afford any product in the presence of subtilisin A, whereas N-Boc-l-phenylalanine could be esterified: Liu, C.-F.; Tam, J. P. Org. Lett. 2001, 3, 4157-4159.
10. T. Ke, and A.M. Klibanov J. Am. Chem. Soc. 121 1999 3334 3340
11. M. Mahmoudian, J. Eaddy, and M. Dawson Biotechnol. Appl. Biochem. 29 1999 229 233
12. M. Tamarez, B. Morgan, G.S.K. Wong, W. Tong, F. Bennett, R. Lovey, J.L. McCormick, and A. Zaks Org. Process Res. Dev. 7 2003 951 953
13. R.L. Hanson, Z. Shi, D.B. Brzozowski, A. Banerjee, T.P. Kissick, J. Singh, A.J. Pullockaran, J.T. North, J. Fan, J. Howell, S.C. Durand, M.A. Montana, D.R. Kronenthal, R.H. Mueller, and R.N. Patel Bioorg. Med. Chem. 8 2000 2681 2687
14. I. Gill, R. Lopez-Fandino, and E. Vulfson J. Am. Chem. Soc. 117 1995 6175 6181
15. A. Zaks, and A.M. Klibanov J. Biol. Chem. 263 1988 3194 3201
16. F. Bordusa Chem. Rev. 102 2002 4817 4867 and references therein.
17. S.-T. Chen, C.-C. Tu, and K.-T. Wang Bioorg. Med. Chem. Lett. 3 1993 539 542
18. J. Partridge, G.A. Hutcheon, B.D. Moore, and P.J. Halling J. Am. Chem. Soc. 118 1996 12873 12877
19. K. Griebenow, and A.M. Klibanov J. Am. Chem. Soc. 118 1996 11695 11699
20. 4 (950:50:5) as the mobile phase at a flow rate of 0.75 ml/min, with the UV detector set at 254 nm.
21. Gao, H.; Mitra, A. K. Tetrahedron Lett. 2000, 41, 1131-1136
22. Vig, B. S.; Lorenzi, P. J.; Mittal, S.; Landowski, C. P.; Shin, H.-C.; Mosberg, H. I.; Hilfinger, J. M.; Amidon, G. L. Pharm. Res. 2003, 20, 1381-1388
23. Aggarwal, S. K.; Gogu, S. R.; Rangan, S. R. S.; Agrawal, K. C. J. Med. Chem. 1990, 33, 1505-1510
24. Kim, D.-K.; Lee, N.; Kim, Y.-W.; Chang, K.; Im, G.-J.; Choi, W.-S.; Kim, K. H. Bioorg. Med. Chem. 1999, 7, 419-424
25. Sriram, D.; Yogeeswari, P.; Srichakravarthy, N.; Ratan Bal, T. Bioorg. Med. Chem. Lett. 2004, 14, 1085-1087.
26. N.M. Mahfouz, and M.A. Hassan J. Pharm. Pharmacol. 53 2001 841 848
27. A.E. Mathew, M.R. Mejillano, J.P. Nath, R.H. Himes, and V.J. Stella J. Med. Chem. 35 1992 145
28. M. Brossat, T.S. Moody, F. de Nanteuil, S.J.C. Taylor, and F. Vaughan Org. Process Res. Dev. 13 2009 706 709