Synthesis of α-P-modified nucleoside diphosphates with ethylenediamine

Journal of the American Chemical Society

Volumn 127, Issue 48, 2005, Pages 16782-16783

  Li, Ping ^a   Xu, Zhihong ^a   Liu, Hongyan ^a   Wennefors, Charlotta K ^a   Dobrikov, Mikhail I ^a   Ludwig, János ^b   Shaw, Barbara Ramsay ^a  

^a DUKE UNIVERSITY   (United States)

^b DeveloGen AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE ANALOG; NUCLEOSIDE DIPHOSPHATE; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLIZATION; DIASTEREOISOMER; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELUTION; OXIDATION; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS;

ADENOSINE DIPHOSPHATE; ANIMALS; CREATINE KINASE; ETHYLENEDIAMINES; MOLECULAR CONFORMATION; MUSCLES; NUCLEOTIDES; PYRUVATE KINASE; RABBITS;

EID: 28844488699     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055179y     Document Type: Article

References (40)

1. For reviews, see: (a) De Clercq, E. J. Clin. Virol. 2004, 30, 115.
2. (b) De Clercq, E. Nat. Rev. Drug Discovery 2002, 1, 13.
3. (c) Wagner, C. R.; Iyer, V. V.; McIntee, E. J. Med. Res. Rev. 2000, 20, 417.
4. (d) Meier, C. Synlett 1998, 233.
5. For reviews, see: (a) Eckstein, F. Biochimie 2002, 84, 841.
6. (b) Eckstein, F. Annu. Rev. Biochem. 1985, 54, 367.
7. For reviews, see: (a) Shaw, B. R.; Dobrikov, M.; Wang, X.; Wan, J.; He, K. Z.; Lin, J. L.; Li, P.; Rait, V.; Sergueeva, Z. A.; Sergueev, D. Ann. N.Y. Acad. Sci. 2003, 1002, 12.
8. (b) Summers, J. S.; Shaw, B. R. Curr. Med. Chem. 2001, 8, 1147.
9. (c) Shaw, B. R.; Sergueev, D.; He, K. Z.; Porter, K.; Summers, J.; Sergueeva, Z.; Rait, V. Methods Enzymol. 2000, 313, 226.
10. (a) Dobrikov, M. I.; Sergueeva, Z. A.; Shaw, B. R. Nucleosides Nucleotides Nucleic Acids 2003, 22, 1651.
11. (b) Dobrikov, M. I.; Grady, K. M.; Shaw, B. R. Nucleosides Nucleotides Nucleic Acids 2003, 22, 275.
12. (c) Li, P.; Shaw, B. R. J. Org. Chem. 2005, 70, 2171.
13. (d) Li, P.; Dobrikov, M.; Liu, H. Y.; Shaw, B. R. Org. Lett. 2003, 5, 2401.
14. (e) Li, P.; Shaw, B. R. Org. Lett. 2002, 4, 2009.
15. (a) Deval, J.; Selmi, B.; Boretto, J.; Egloff, M. P.; Guerreiro, C.; Sarfati, S.; Canard, B. J. Biol. Chem. 2002, 277, 42097.
16. (b) Selmi, B.; Boretto, J.; Sarfati, S. R.; Guerreiro, C.; Canard, B. J. Biol. Chem. 2001, 276, 48466.
17. (c) Meyer, P.; Schneider, B.; Sarfati, S.; Deville-Bonne, D.; Guerreiro, C.; Boretto, J.; Janin, J.; Veron, M.; Canard, B. EMBO J. 2000, 19, 3520.
18. (d) Matamoros, T.; Deval, J.; Guerreiro, C.; Mulard, L.; Canard, B.; Menendez-Arias, L. J. Mol. Biol. 2005, 349, 451.
19. (e) Alvarez, K.; Deval, J.; Barral, K.; De Michelis, C.; Canard, B. Antiviral Res. 2005, 65, A49.
20. (f) Deval, J.; Alvarez, K.; Selmi, B.; Bermond, M.; Boretto, J.; Guerreiro, C.; Mulard, L.; Canard, B. J. Biol. Chem. 2005, 280, 3838.
21. (a) Li, P.; Shaw, B. R. J. Org. Chem. 2004, 69, 7051.
22. (b) Lin, J. L.; He, K. Z.; Shaw, B. R. Helv. Chim. Acta 2000, 83, 1392.
23. Burgess, K.; Cook, D. Chem. Rev. 2000, 100, 2047.
24. (a) Ludwig, J.; Eckstein, F. J. Org. Chem. 1989, 54, 631.
25. (b) Carrasco, N.; Huang, Z. J. Am. Chem. Soc. 2004, 126, 448.
26. (c) He, K. H.; Hasan, A.; Krzyzanowska, B.; Shaw, B. R. J. Org. Chem. 1998, 63, 5769.
27. (d) Krzyzanowska, B. K.; He, K. Z.; Hasan, A.; Shaw, B. R. Tetrahedron 1998, 54, 5119.
28. Ludwig, J.; Eckstein, F. J. Org. Chem. 1991, 56, 1777.
29. Wang, G. Y.; Boyle, N.; Chen, F.; Rajappan, V.; Pagan, P.; Brooks, J. L.; Hurd, T.; Leeds, J. M.; Rajwanshi, V. K.; Jin, Y.; Prhavc, M.; Bruice, T. W.; Cook, P. D. J. Med. Chem. 2004, 47, 6902.
30. -].
31. (a) Gail, R.; Costisella, B.; Ahmadian, M. R.; Wittinghofer, A. Chembiochem 2001, 2, 570.
32. (b) Knorre, D. G.; Kurbatov, V. A.; Samukov, V. V. FEBS Lett. 1976, 70, 105.
33. (a) Phosphoroselenoate has recently emerged as an interesting phosphate analogue due to its applications in X-ray structure analysis of nucleic acids. See ref 8b and Hobartner, C.; Micura, R. J. Am. Chem. Soc. 2004, 126, 1141.
34. (b) To the best of our knowledge, the approach reported here represents the only other method to prepare NDPαSe in addition to the oxathiaphospholane methodology by Misiura, K.; Szymanowicz, D.; Stec, W. J. Org Lett 2005, 7, 2217.
35. Major, D. T.; Nahum, V.; Wang, Y. F.; Reiser, G.; Fischer, B. J. Med. Chem. 2004, 47, 4405.
36. (a) Lister, G. M. S.; Jones, R. J. Phys. Condens. Matter 1989, 1, 6039.
37. (b) Summers, J. S.; Roe, D.; Boyle, P. D.; Colvin, M.; Shaw, B. R. Inorg. Chem. 1998, 37, 4158.
38. (c) Volk, D. E.; Power, T. D.; Gorenstein, D. G.; Luxon, B. A. Tetrahedron Lett. 2002, 43, 4443.
39. Krishnan, P.; Fu, Q.; Lam, W.; Liou, J. Y.; Dutschman, G.; Cheng, Y. C. J. Biol. Chem. 2002, 277, 5453.
40. Borders, C. L.; Snider, M. J.; Wolfenden, R.; Edmiston, P. L. Biochemistry 2002, 41, 6995.