Base catalysis and leaving group dependence in intramolecular alcoholysis or uridine 3'-(aryl phosphorothioate)s

Journal of the American Chemical Society

Volumn 118, Issue 34, 1996, Pages 7921-7928

  Aimer, Helena ^a   Strömberg, Roger ^a,b  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHOROTHIOIC ACID DERIVATIVE; URIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029788767     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953399d     Document Type: Article

References (49)

1. Knowles, J. R. Annu. Rev. Biochem. 1980, 49, 877.
2. Eckstein, F. Angew. Chem., Int. Ed. Engl. 1983, 22, 423.
3. Eckstein, F. Annu. Rev. Biochem. 1985, 54, 367.
4. Eckstein, F.; Gish G. TIBS 1989, 14, 97.
5. Frey, P. A. Adv. Enzymol. Relat. Areas Mol. Biol. 1989, 62, 119.
6. Wagner, R. W. Nature 1994, 372, 333.
7. Uhlmann, E.; Peymann, A. Chem. Rev. 1990, 90, 543.
8. Mizrahi, V.; Henrie R. N.; Marlier J: F.; Johnson K. A.; Bencovic, S. J. Biochemistry 1985, 24, 4010.
9. McSwiggen, J. A.; Cech, T. R. Science 1989, 244, 679.
10. Herschlag, D.; Piccirilli, J. A.; Cech, T. R. Biochemistry 1991, 30, 4844.
11. Herschlag, D. J. Am. Chem. Soc. 1994, 116, 11631.
12. Breslow, R.; Katz, I. J. Am. Chem. Soc. 1968, 90, 7376.
13. Hollfelder, F.; Herschlag, D. Biochemistry 1995, 34, 12255.
14. Ketelaar, J. A. A.; Gersmann, H. R.: Koopmans, K. Red. Trav. Chim. Phys-Bas 1952, 71, 1253.
15. Fanni, T.; Taira, K.; Gorenstein, D. G.; Vaidyanathaswany, R.; Verkade, J. G. J. Am. Chem. Soc. 1986, 108, 6311.
16. Eckstein, F. FEBS Lett. 1968, 2, 85.
17. Smrt, J.; Malkiewicz, A. Collect. Czech. Chem. Commun. 1973, 38, 2962.
18. Burgers, P. M. J.; Eckstein, F. Biochemistry 1979, 18, 592.
19. Almer, H.; Strömberg, R. Tetrahedron Lett. 1991, 32, 3723.
20. Oivanen, M.; Ora, M.; Almer, H.; Strömberg, R.; Lönnberg H. J. Org. Chem. 1995, 60, 5620.
21. Davis, A. M.; Hall, A. D.; Williams, A. J. Am. Chem. Soc. 1988, 110, 5105.
22. Garegg, P. J.; Regberg, T.; Stawinski, J.; Strömberg, R. Chem. Scr. 1985, 25, 280.
23. Garegg, P. J.; Regberg, T.; Stawinski, J.; Strömberg, R. Chem. Scr. 1986, 26, 59.
24. Froehler, B. C.; Matteucci, M. D. Tetrahedron Lett. 1986, 27, 469.
25. Strömberg, R. Chem. Commun. Stockholm Univ. 1987, 1.
26. Stawinski, J.; Strömberg, R. Trends Org. Chem. 1993, 4, 31.
27. Almer, H.; Stawinski, J.; Strömberg, R.; Thelin, M. J. Org. Chem. 1992, 57, 6163.
28. Seela, F.; Kretschmer, U. J. Org. Chem. 1991, 56, 3861.
29. Battistini, C.; Brasca, M. G.; Fustinoni, S.; Lazzari, E. Tetrahedron 1992, 48, 3209.
30. Szabó, T.; Almer, H.; Strömberg, R.; Stawinski, J. Nucleosides Nucleotides 1995, 14, 715.
31. Garegg, P. J.; Regberg, T.; Stawinski, J.; Strömberg, R. Nucleosides Nucleotides 1987, 6, 655.
32. Kuyl-Yeheskiely, E.: Spierenberg, M.; van den Elst, H.; Tromp, M.; van der Marel, G. A.; van Boom, J. H. Reel. Trav. Chim. Pays-Bas 1986, 105, 505.
33. Strömberg, R.; Stawinski. J. Nucleic Acids Res. Symp. Ser. 1987, 18, 185.
34. Brown, H. C.; Fletcher R. S., J. Am. Chem. Soc. 1949, 71, 1845.
35. Moore, J. W.; Pearson, R. G. Kinetics and Mechanism, 3rd ed.; John Wiley & Sons: New York and Chichester, 1981.
36. Kirby, A. J.; Marriott. R. E. J. Am. Chem. Soc. 1995, 117, 833.
37. Frey. P. A,; Sammons, R. D. Science 1985, 228, 541.
38. Kirby, A. J.; Younas, M. J. Chem. Soc., Sect. B 1970, 1165.
39. Thea, S.; Williams, A. Chem. Soc. Rev. 1986, 15, 125.
40. Williams, A. Acc. Chem. Res. 1984, 17, 425.
41. Leffler, J. E. Science 1953, 117, 340.
42. Bordwell, F. G.; Boyle, W. J. J. Am. Chem. Soc. 1972, 94, 3907.
43. Pross, A. Tetrahedron Lett. 1983, 835
44. Bourne, N.; Williams, A. J. Org. Chem. 1984, 1200 (1984).
45. Hopkins, A.; Day, R. A.; Williams, A. J. Am. Chem. Soc. 1983, 105, 6062.
46. Cullis, P. M.; Iagrossi, A. J. Am. Chem. Soc. 1986, 108, 7870.
47. Cullis, P. M.; Misra, R.; Wilkins, D. J. J. Chem. Soc., Chem. Commun. 1987, 1594.
48. Harnett, S. P.; Lowe, G. J. Chem. Soc., Chem. Commun. 1987, 1416.
49. Hall, A. D.; Williams, A. Biochemistry 1979, 25, 4784.