Stereochemical course of cerium(IV)-catalyzed hydrolysis of cyclic nucleotides

Journal of the American Chemical Society

Volumn 121, Issue 26, 1999, Pages 6125-6130

  Cullis, Paul M ^a   Snip, Erwin ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CERIUM; CYCLIC AMP; CYCLIC NUCLEOTIDE; CYCLIC THYMIDINE MONOPHOSPHATE; HYDROXYL GROUP; THIMIDINE 5' THIOPHOSPHATE; THYMIDINE 3' THIOPHOSPHATE; THYMIDINE 3',5' CYCLIC THIOPHOSPHATE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; HYDROLYSIS; NUCLEOTIDE METABOLISM; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0033532950     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990686z     Document Type: Article

References (43)

1. (a) Buchwald, S. L.; Hansen, D. E.; Hassett, A.; Knowles, J. R.; Methods Enzymol. 1982, 87, 279-301.
2. (b) Lowe, G. Acc. Chem. Res. 1983, 16, 244.
3. (c) Eckstein, F. Angew. Chem., Int. Ed. Engl. 1983, 22, 423.
4. (d) Frey, P. A. Tetrahedron 1982, 38, 1541.
5. Gani, D.; Wilkie, J. Chem. Soc. Rev. 1995, 24, 55.
6. Wilkie, J.; Gani, D. J. Chem. Soc., Perkin Trans. 2 1996, 783 and reference cited therein.
7. (a) Takeda, N.; Imai, T.; Irisawa, M.; Sumaoka, J.; Yashiro, M.; Shigekawa, H.; Komiyama, M. Chem. Lett. 1996, 599.
8. (b) Takasaki, B. K.; Chin, J. J. Am. Chem. Soc. 1995, 117, 8582.
9. (c) Wahnon, D.; Lebuis, A.-M.; Chin, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412.
10. (d) Young, M. J.; Wahnon, D.; Hynes, R. C.; Chin, J. J. Am. Chem. Soc. 1995, 117, 9441.
11. (e) Tsubouchi, A.; Bruice, T. C. J. Am. Chem. Soc. 1994, 116, 11614.
12. (f) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893.
13. (g) Takasaki, B. K.; Chin, J. J. Am. Chem. Soc. 1994, 116, 1121.
14. (h) Schneider, H.-J.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.
15. (i) Takasaki, B. K.; Chin, J. J. Am. Chem. Soc. 1993, 115, 9337.
16. (a) Komiyama, M.; Takeda, N.; Takahashi, Y.; Uchida, H.; Shiiba, T.; Kodama, T.; Yashiro, M. J. Chem. Soc., Perkin Trans. 2 1995, 269.
17. (b) Sumaoka, J.; Miyama, S.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1994, 1755.
18. (c) Sumaoka, J.; Yashiro, M.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1992, 1707.
19. (a) Buchwald, S. L.; Knowles, J. R. J. Am. Chem. Soc. 1982, 104, 1438.
20. (b) Cullis, P. M.; Rous, A. J. J. Am. Chem. Soc. 1985, 107, 6721.
21. (c) Buchwald, S. L.; Pliura, D. H.; Knowles, J. R. J. Am. Chem. Soc. 1984, 106, 4916.
22. (d) Buchwald, S. L.; Friedman, J. M.; Knowles, J. R. J. Am. Chem. Soc. 1984, 106, 4911.
23. (e) Cullis, P. M.; Iagrossi, A. J. Am. Chem. Soc. 1986, 108, 7870.
24. (f) Freeman, S.; Friedman, J. M.; Knowles, J. R. J. Am. Chem. Soc. 1987, 109, 3166.
25. Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70.
26. (a) Coderre, J. A.; Mehdi, S.; Gerlt, J. A. J. Am. Chem. Soc. 1981, 103, 1870.
27. (b) Burgers, P. M. J.; Eckstein, F.; Hunneman, D.; Baraniak, J.; Kinas, R. W.; Lesiak, K.; Stec, W. J. J. Biol. Chem. 1979, 254, 9959.
28. Hart, F. A. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergammon Press: New York, 1987; Vol. 3, p 1059.
29. (a) Eliseeva, G. D.; Baranskii, V. A.; Sukhorukova, N. A. J. Gen. Chem., USSR 1988, 58, 687.
30. (b) Eliseeva, G. D.; Baranskii, V. A.; Sukhorukova, N. A. J. Gen. Chem., USSR 1987, 57, 52.
31. (c) Neimysheva, A. A.; Savchik, V. I.; Ermolaeva, M. V.; Knunyants, I. L. Bull. Acad. Sci. USSR 1968, 2104.
32. Zielinski, W. S.; Stec, W. J. J. Am. Chem. Soc. 1977, 99, 8365.
33. (a) Jarvest, R. L.; Lowe, G.; Potter, B. V. L. J. Chem. Soc., Perkin Trans, 1 1981, 3187.
34. (b) Kathyshkina, V. V.; Kraft, M. Y. Zh. Obshch. Khim. 1956, 26, 3060.
35. (c) Cremlyn, R. J. W.; David, J.; Kishore, N. J. Chem. Soc., Perkin Trans, 1 1972, 583.
36. Hamblin, M. R.; Cummins, J. H.; Potter, B. V. L. Biochem. J. 1987, 241, 827.
37. (a) Lowe, G.; Potter, B. V. L.; Sproat, B. S.; Hull, W. E. J. Chem. Soc., Chem. Commun. 1979, 733.
38. (b) Cohn, M.; Hu, A. J. Am. Chem. Soc. 1980, 102, 913.
39. (a) Thatcher, G. R. J.; Kluger, R. H. Adv. Phys. Org. Chem. 1989, 25, 99.
40. (b) Hall, C. R.; Inch, T. D. Tetrahedron 1980, 36, 2059.
41. Van Ool, P. J. J. M.; Buck, H. M. Eur. J. Biochem. 1982, 121, 329.
42. Mehdi, S.; Coderre, J. A.; Gerlt, J. A. Tetrahedron 1983, 39, 3483.
43. Anslyn, E.; Breslow, R. J. Am. Chem. Soc. 1989, 111, 4473.