Hydrolysis of thymidine boranomonophosphate and stepwise deuterium substitution of the borane hydrogens. 31P and 11B NMR studies

Journal of the American Chemical Society

Volumn 118, Issue 28, 1996, Pages 6606-6614

  Li, Hong ^a   Hardin, Charles ^b   Shaw, Barbara Ramsay ^a  

^a DUKE UNIVERSITY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBORON DERIVATIVE;

ARTICLE; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029934395     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9540280     Document Type: Article

References (38)

1. Sood, A.; Shaw, B. R.; Spielvogel, B. F. J. Am. Chem. Soc. 1990, 112, 9000-9001.
2. Tomasz, J.; Shaw, B. R.; Porter, K.; Spielvogel, F.; Sood, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1373-1375.
3. Shaw, B. R.; Madison, J.; Sood, A.; Spielvogel, B. F. Methods Mol. Biol. 1993, 20, 225-243.
4. Porter, K.; Ealey, K.; Briley, J. D.; Huang, F.; Shaw, B. R. Genome Sequencing and Analysis Conference VI, Hilton Head, SC; Mary Ann Liebert, Inc.: New York, 1994; p 43.
5. Li, H.; Porter, K.; Huang, F.; Shaw, B. R. Nucleic Acids Res. 1995, 21, 4495-4501.
6. (a) Porter, K.; Briley, J. D.; Tomasz, J.; Sood, A.; Spielvogel, B. F.; Shaw, B. R. Genome Sequencing and Analysis Conference V, Hilton Head, SC; Mary Ann Liebert, Inc.: New York, 1993; p 55.
7. (b) Porter, K.; Briley, J. D.; Shaw, B. R. Genome Sequencing and Analysis Conference VI, Hilton Head, SC; Mary Ann Liebert, Inc.: New York, 1994; p 43.
8. Ramaswamy, M.; Shaw, B. R. Manuscript in preparation.
9. Huang, F.; Sood, A.; Spielvogel, B. F.; Shaw, B. R. J. Biomol. Struct. Dyn. 1993, 10, a078.
10. (a) Huang, F. Ph.D. Thesis; Duke University, Durham, NC, 1994.
11. (b) Huang, F.; Sood, A.; Spielvogel, B. F.; Shaw, B. R. Eighth International Meeting on Boron Chemistry; The University of Tennessee: Knoxville, TN, 1993; p 114.
12. (c) Huang, F.; Shaw, B. R. Manuscript in preparation.
13. The actual ionization states of thymidine boranomonophosphate, boranophosphate, phosphonate (or phosphite), and boric acid in solution are both pH- and ionic strength-dependent. For convenience, we show thymidine boranomonophosphate, boranophosphate, and phosphonate in their fully deprotonated forms, and boric acid in its fully protonated form. This probably does not reflect the actual protonation states of these molecules at pH 5-6 (vide infra). The state of protonation is not the subject of the present paper.
14. Borer, P. N. Nucleic Acids. In Handbook of Biochemistry and Molecular Biology, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Cleveland, OH, 1975; Vol. 1, p 589.
15. (a) The rate-pH profile of the thymidine boranomonophosphate hydrolysis in ref 9 indicated that the rate constants change by less than 25% over the pH range from 3 to 6.5.
16. 31P chemical shift changes is not apparent. These changes could be due to a pH change as a result of hydrolysis, chemical exchange among different species, or an equilibrium isotope effect.
17. (a) Harris, R. K. Nuclear Magnetic Resonance Spectroscopy: A Physicochemical View; Longman Scientific & Technical, Somerset, NJ, 1986.
18. (b) Eaton, G. R.; Lipscomb, W. N. NMR Studies of Boron Hydrides and Related Compounds; W. A. Benjamin., Inc.: New York, 1969.
19. Schaeffer, R. Progress in Boron Chemistry; The MacMillan Co.: New York, 1964; Vol. 1.
20. Wood, D. J.; Hruska, F. E.; Ogilvie, K. K. Can. J. Chem. 1974, 52, 3353-3366.
21. Onak, T. P.; Labdesman, H.; Williams, R. E.; Shapiro, I. J. Phys. Chem. 1959, 63, 1533-1535.
22. Stec, W. J.; Goddard, N.; van Wazer, J. R. J. Phys. Chem. 1971, 75, 3547-3549.
23. Thatcher, G. R. J.; Kluger, R. H. Adv. Phys. Org. Chem. 1989, 25, 99-265.
24. Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70-78.
25. Thatcher, G. R. J.; Campbell, S. J. Org. Chem. 1993, 58, 2272-2278.
26. Davis, R. E.; Swain, C. G. J. Am. Chem Soc. 1960, 82, 5949-5950.
27. Mesmer, R. E.; Jolly, W. L. Inorg. Chem. 1962, 1, 608-612.
28. Davis, R. E.; Bromels, E. B.; Kibby, C. L. J. Am. Chem. Soc. 1962, 84, 885-892.
29. Gardiner, J. A.; Collat, J. W. J. Am. Chem. Soc. 1965, 87; 1692-1700.
30. Gardiner, J. A.; Collat, J. W. Inorg. Chem 1965, 4, 1208-1212.
31. Levine, L. A.; Kreevoy, M. M. J. Am. Chem. Soc. 1972, 94, 3346-3394.
32. Kidd, R. G. NMR of Newly Accessible Nuclei; Academic Press, Inc.,-New York, 1983; Vol. 2.
33. Hansen, P. E. Prog. NMR Spectrosc. 1988, 20, 207-255.
34. Rankothge, H. M.; Hook, J.; van Gorkom, L.; Moran, G. Magn. Reson. Chem. 1994, 32, 446-451.
35. Kreevoy, M. M.; Hutchins, J. E. C. J. Am. Chem. Soc. 1969, 91, 4329-4330.
36. Kreevoy, M. M.; Hutchins, J. E. C. J. Am. Chem. Soc. 1972, 94, 6371-6376.
37. Crutchfield, M. M.; Dungan, C. H; van Wazer, J. R. Top. Phosphorus Chem. 1967, 5, 1-74.
38. Stawinski, J. Handbook of Organophosphorus Chemistry; Marcel Dekker, Inc.: New York, 1992; pp 377-434.