A novel method for the preparation of nucleoside triphosphates from activated nucleoside phosphoramidates

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2257-2260

  Wu, Weidong ^a   Meyers, Caren L Freel ^a   Borch, Richard F ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE TRIPHOSPHATE; PHOSPHORAMIDIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

AMIDES; DIPHOSPHATES; NUCLEOTIDES; PHOSPHORIC ACIDS; PYRROLIDINES; THYMIDINE; THYMINE NUCLEOTIDES;

EID: 3142683066     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049267j     Document Type: Article

References (37)

1. Burgess, K.; Cook, D. Chem. Rev. 2000, 100, 2047-60.
2. Ludwig, J. Acta Biochim. Biophys. Acad. Sci. Hung. 1981, 16, 131-3.
3. Ruth, J. L.; Cheng, Y. C. Mol. Pharmacol. 1981, 20, 415-22 .
4. Yoshikawa, M.; Kato, T.; Takenishi, T. Tetrahedron Lett. 1967, 50, 5065-8.
5. Wu, W.; Bergstrom, D. E.; Davisson, V. J. J. Org. Chem. 2003, 68, 3860-5.
6. (a) Tomasz, J.; Simoncsits, A.; Kajtar, M.; Krug, R. M.; Shatkin, A. J. Nucleic Acids Res. 1978, 5, 2945-57.
7. (b) Simoncsits, A.; Tomasz, J. Nucleic Acids Res. 1975, 2, 1223-33.
8. (a) Moffatt, J. G.; Khorana, H. G. J. Am. Chem. Soc. 1961, 83, 649-58.
9. (b) Moffatt, J. G. Can. J. Chem. 1964, 42, 599-604.
10. (c) van Boom, J. H.; Crea, R.; Luyten, W. C.; Vink, A. B. Tetrahedron Lett. 1975, 16, 2779-82.
11. (a) Hoard, D. E.; Ott, D. G. J. Am. Chem. Soc. 1965, 87, 1785-8.
12. (b) Shimazu, M.; Shinozuka, K.; Sawai, H. Tetrahedron Lett. 1990, 31, 235-8.
13. (a) Freel Meyers, C. L.; Hong, L.; Joswig, C.; Borch, R. F. J. Med. Chem. 2000, 43, 4313-8.
14. (b) Freel Meyers, C. L.; Borch, R. F. J. Med. Chem. 2000, 43, 4319-27.
15. (c) Tobias, S. C.; Borch, R. F. J. Med. Chem. 2001, 44, 4475-80.
16. (d) Tobias, S. C.; Borch, R. F. Mol. Pharm. 2004, 1, 112-6.
17. Freel Meyers, C. L.; Borch, R. F. Org. Lett. 2001, 3, 3765-8.
18. Freel Meyers, C. L.; Borch, R. F. Org. Lett. 2003, 5, 341-4.
19. Ludwig, J.; Eckstein, F. J. Org. Chem. 1989, 54, 631-5.
20. Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Muehlbacher, M.; Poulter, C. D. J. Org. Chem, 1986, 51, 4768-79.
21. 13 the absence of hydrolysis byproduct indicates that nucleophilicity of this pyrophosphate salt is much greater toward the phosphoramidate zwitterion intermediate than that of water.
22. It is important to use only 1 equiv of pyrophosphate reagent in these reactions, because excess pyrophosphate is very difficult to separate from nucleoside triphosphate during purification by an ion exchange chromatography on Q Sepharose FF.
23. (a) Crotty, S.; Maag, D.; Arnold, J. J.; Zhong, W.; Lau, J. Y.; Hong, Z.; Andino, R.; Cameron, C. E. Nat. Med. 2000, 6, 1375-9.
24. (b) Crotty, S.; Cameron, C. E.; Andino, R. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 6895-900.
25. (c) Maag, D.; Castro, C.; Hong, Z.; Cameron, C. E. J. Biol. Chem. 2001, 276, 46094-8.
26. (d) Crotty, S.; Cameron, C.; Andino, R. J. Mol. Med. 2002, 80, 86-95.
27. (a) Furth, J. J.; Cohen, S. S. Cancer Res. 1968, 28, 2061-7.
28. (b) Graham, F. L.; Whitmore, G. F. Cancer Res. 1970, 30, 2636-44.
29. (c) Kufe, D. W.; Major, P. P.; Egan, E. M.; Beardsley, G. P. J. Biol. Chem. 1980, 255, 8997-900.
30. (d) Major, P. P.; Egan, E. M.; Beardsley, G. P.; Minden, M. D.; Kufe, D. W. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 3235-9.
31. 31P NMR with no formation of hydrolysis byproduct even in the presence of water.
32. (a) Griffin, B. E.; Jarman, M.; Reese, C. B.; Sulston, J. E. Tetrahedron 1967, 23, 2301-13.
33. (b) Jones, S. S.; Rayner, B.; Reese, C. B.; Ubasawa, A.; Ubasawa, M. Tetrahedron 1980, 36, 3075-85.
34. Davisson, V. J.; Davis, D. R.; Dixit, V. M.; Poulter, C. D. J. Org. Chem. 1987, 52, 1794-801.
35. (a) van der Marel, G. A.; van Boeckel, C. A.; Wille, G.; van Boom, J. H. Nucleic Acids Res. 1982, 10, 2337-51.
36. (b) van der Marel, G. A.; van Boeckel, C. A.; Wille, G.; van Boom, J. H. Tetrahedron Lett. 1981, 22, 3887-90.
37. (c) van Boeckel, C. A. A.; van der Marel, G.; Wille, G.; van Boom, J. H. Chem. Lett. 1981, 1725-8.