Protease-mediated preparation of valganciclovir intermediate

Journal of Molecular Catalysis B: Enzymatic

Volumn 108, Issue , 2014, Pages 77-81

  Sethi, Madhuresh K ^a   Bhandya, Somashekar R ^a   Shukla, Rohit ^a   Kumar, Anish ^a   Maddur, Nagaraj ^a   Mittapalli, V S N Jayalakshmi ^a   Rawat, Vijendra Singh ^a   Yerramalla, Raja Krishna ^a  

^a Research and Development Center   (India)

Author keywords

2 (2 amino 6 oxo 1; 6 dihydro 9H purin 9 yl)methoxy 3 hydropropyl N (benzyloxy)carbonyl l valinate; Alcalase 2.4L; enzymatic; Protex 6L; Valganciclovir hydrochloride

Indexed keywords

CATALYSIS;

ALCALASE; ENZYMATIC; METHOXY; PROTEX 6L; VALGANCICLOVIR HYDROCHLORIDE;

BACTERIOLOGY;

2[(2 AMINO 6 OXO 1,6 DIHYDRO 9H PURIN 9 YL)METHOXY] 3 HYDROPROPYL N [(BENZYLOXY)CARBONYL] LEVO VALINATE; ALKALINE PROTEINASE; SUBTILISIN; UNCLASSIFIED DRUG; VALGANCICLOVIR;

ARTICLE; BACILLUS LICHENIFORMIS; BIOCATALYST; CARBON NUCLEAR MAGNETIC RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84905008323     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2014.07.004     Document Type: Article

References (51)

1. K.G. Au Eong, S. Beatty, and S.J. Charles Singapore Med. J. 41 2000 298 300
2. I.G. Sia, and R. Patel Clin. Microbiol. Rev. 13 2000 83 121
3. P.G. Tranos, I. Georgalas, P. Founti, and I. Ladas Clin. Ophthamol. 2 2008 961 963
4. I. Yust, Z. Fox, and M. Burke Eur. J. Clin. Microbiol. Infect. Dis. 23 2004 550 559
5. M. Curran, and S. Noble Drugs 61 2001 1145 1150
6. J.C. Martin, M.A. Tippie, D.P.C. McGee, and J.P.H. Verheyden J. Pharm. Sci. 76 1987 180 184
7. C. Steininger Recent Patent. Anti-Infect. Drug Discover. 2 2007 53 72
8. According to Food and Drug Administration (FDA) specifications, the diastereomeric ratio of Valganciclovir should be maintained in the range 55:45 to 45:55.
9. G.M. Reddya, V.V.N.K.V.P. Rajua, K. Satyanarayanaa, R. Vedantham, and G. Venkateshwarlub Synth. Commun. 43 2013 425 430
10. K.S. Babu, P. Srinivas, Y.V. Madhavi, I. Babu, G.M. Reddy, P. Haldar, P.N. Rao, V. Krishna, K. Srinivas, G. Venkateshwarulu, P.P. Reddy, and R.V. Anand Arkivok 2011 199 208
11. H.B. Arzeno, United States Patent 5700936 (1997).
12. H.B. Arzeno, E.R. Humphreys, United States Patent 5756736 (1998).
13. H.B. Arzeno, E.R. Humphreys, C.R. Roberts, J. Wong, United States Patent 5840890 (1998).
14. H. Maag, J.J. Nestor, United States Patent 5856481 (1999).
15. H. Maag, J.J. Nestor, United States Patent 5840891 (1998).
16. H. Maag, J.J. Nestor, S.W. Womble, United States Patent 6083953 (1998).
17. H.B. Arzeno, E.R. Humphreys, C.R. Roberts, J. Wong, United States Patent 6103901 (2000).
18. H.B. Arzeno, S.D. Axt, C.C. Beard, C.A. Dvorak, P.R. Fatheree, L.E. Fisher, Y. Han, E.R. Humphreys, J.P. Lund, S. Nguyen, C.R. Roberts, D.L. Wren, United States Patent 6040446 (2000).
19. C.A. Dvorak, D.L. Wren, L.E. Fisher, S.D. Axt, E.R. Humphreys, H.B. Arzeno, C.C. Beard, S. Nguyen, Y. Han, C.R. Roberts, J.P. Lund, P.R. Fatheree United States Patent 6215017 (2001).
20. C. A. Dvorak, D.L. Wren, L.E. Fisher, S.D. Axt, E.R. Humphreys, H.B. Arzeno, C.C. Beard, S. Nguyen, Y. Han, C.R. Roberts, J.P. Lund, P.R. Fatheree, United States Patent 6218568 (2001).
21. D.R. Rao, N. Kankan, P. Pande, United States Patent 0225305 (2007).
22. P. Engelhardt, M. Hogberg, N. Johansson, X. Zhou, B. Lindborg, World Patent 199727197 (1997).
23. D.R. Rao, N. Kankan, P. Pande, European Patent 1837336 (2007).
24. M.K. Sethi, M. Hussain, V.S. Rawat, R. Yaramalla, D. Dutta, India Patent Application No. 2378/CHE/2008.
25. C. Bohm, W.F. Austin, and D. Trauner Tetrahedron: Asymmetry 14 2003 71 74
26. C. Neri, and J.M. Williams J. Adv. Synth. Catal. 345 2003 835 848
27. I.M. Fellows, D.E. Kaelin, and S.F. Martin J. Am. Chem. Soc. 122 2000 10781 10787
28. D.B. Kastrinsky, and D.L. Boger J. Org. Chem. 69 2004 2284 2289
29. K. Takabe, N. Mase, H. Hashimoto, A. Tsuchiya, T. Ohbayasi, and H. Yoda Bioorg. Med. Chem. Lett. 13 2003 1967 1971
30. T. Yokomatsu, K. Takada, A. Yasumoto, Y. Yuasa, and S. Shibuya Heterocycles 56 2002 545 552
31. K. Takabe, Y. Iida, H. Hiyoshi, M. Ono, Y. Hirose, Y. Fukui, H. Yoda, and N. Mase Tetrahedron: Asymmetry 11 2000 4825 4829
32. M. Murata, Y. Terao, K. Achiwa, T. Nishio, and K. Seto Chem. Pharm. Bull. 10 1989 2670 2673
33. Y. Terao, M. Murata, K. Achiwa, T. Nishio, M. Akamtsu, and M. Kamimura Tetrahedron Lett. 29 1988 5173 5176
34. Y.F. Wang, J.J. Lalonde, M. Momongan, D. Bergbreiter, and C.H. Wong J. Am. Chem. Soc. 110 1988 7200 7205
35. D.J. Ramon, and M. Yus Curr. Org. Chem. 8 2004 149 152
36. E.J. Corey, and A. Guzman-Perez Angew. Chem. Int. Ed. 37 1998 388 401
37. R. Chênevert, and G. Courchesne Tetrahedron Lett. 43 2002 7971 7974
38. R. Chênevert, G.M. Ziarani, M.P. Morin, and M. Dasser Tetrahedron: Asymmetry 10 1999 3117 3122
39. D. Breitgoff, K. Laumen, and M. Schneider J. Chem. Soc. Chem. Commun. 110 1988 7200 7205
40. B. Wirz, R. Schmid, and J. Foricher Tetrahedron: Asymmetry 3 1992 137 142
41. H. Suemune, Y. Mizuhara, H. Akita, and K. Sakai Chem. Pharm. Bull. 34 1986 3440 3444
42. V. Kerschner, and W. Kreiser Tetrahedron Lett. 28 1987 531 534
43. Y.F. Wang, J.J. Lalonde, M. Momongan, D. Bergbreiter, and C.H. Wong J. Am. Chem. Soc. 110 1988 7200 7205
44. V. Bódai, L. Novák, and L. Poppe Synlett 1999 759 761
45. M. Kirihara, M. Kawasaki, T. Takuwa, H. Kakuda, T. Wakikawa, Y. Takeuchi, and K.L. Kirk Tetrahedron: Asymmetry 14 2003 1753 1761
46. J.W. Lane, and R.L. Halcomb J. Org. Chem. 68 2003 1348 1357
47. D.B. Berkowitz, S. Choi, and J.H. Maeng J. Org. Chem. 65 2000 847 860
48. R. Chenevert, and M. Dickmann J. Org. Chem. 61 1996 3332 3341
49. M.J. Homann, R. Vail, B. Morgan, V. Sabesan, C. Levy, D.R. Dodds, and A. Zaks Adv. Synth. Catal. 343 2001 744 749
50. M.S. Yu, I. Lantos, Z.-Q. Peng, J. Yu, and T. Cacchio Tetrahedron Lett. 41 2000 5647 5651
51. L.M. Beauchamp, United States Patent 5043339 (1991).