Comparisons of phosphorothioate and phosphate monoester transfer reactions: Activation parameters, solvent effects, and the effect of metal ions

Journal of the American Chemical Society

Volumn 121, Issue 10, 1999, Pages 2156-2163

  Catrina, Irina E ^a   Hengge, Alvan C ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHATE; PHOSPHOROTHIOIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONFORMATIONAL TRANSITION; ENTHALPY; HYDROLYSIS; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PH; REACTION ANALYSIS; SOLVATION; THERMODYNAMICS;

EID: 0033577278     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983862x     Document Type: Article

References (28)

1. Breslow, R.; Katz, I. J. Am. Chem. Soc. 1968, 90, 7376-7377.
2. Chlebowski, J. F.; Coleman, J. E. J. Biol. Chem. 1974, 249, 7192-7202.
3. Han, R.; Coleman, J. E. Biochemistry 1995, 34, 4238-4245.
4. Hollfelder, F.; Herschlag, D. Biochemistry 1995, 34, 12255-12264.
5. Herschlag, D.; Jencks, W. P. Biochemistry 1990, 29, 5172-5179.
6. For a description of the IUPAC nomenclature for reaction mechanisms, see: Guthrie, R. D.; Jencks, W. P. Acc. Chem. Res. 1989, 22, 343-349.
7. Kirby, A. J.; Jencks, W. P. J. Am. Chem. Soc. 1965, 87, 3209-3216.
8. Kirby, A. J.; Varvoglis, A. G. J. Am. Chem. Soc. 1967, 89, 415-423.
9. Friedman, J. M.; Freeman, S.; Knowles, J. R. J. Am. Chem. Soc. 1988, 110, 1268-1275.
10. Buchwald, S. L.; Friedman, J. M.; Knowles, J. R. J. Am. Chem. Soc. 1984, 106, 4911-4916.
11. Hoff, R. H.; Hengge, A. C. J. Org. Chem. 1998, 63, 6680-6688.
12. Iyengar, R.; Eckstein, F.; Frey, P. A. J. Am. Chem. Soc. 1984, 106, 8309-8310.
13. Liang, C.; Allen, L. C. J. Am. Chem. Soc. 1987, 109, 6449-6453.
14. Cullis, P. M.; Iagrossi, A. J. Am. Chem. Soc. 1986, 108, 7870-7871.
15. Cullis, P. M.; Misra, R.; Wilkins, D. J. J. Chem. Soc. Chem. Commun. 1987, 1594-1596.
16. Domanico, P.; Mizrahi, V.; Benkovic, S. J. In Mechanisms of enzymatic reactions: stereochemistry; Frey, P. A., Ed.; Elsevier: New York, 1986; pp 127-137.
17. Burgess, J.; Blundell, N.; Cullis, P. M.; Hubbard, C. D.; Misra, R. J. Am. Chem. Soc. 1988, 110, 7900-7901.
18. Meyerson, S.; Harvan, D. J.; Hass, J. R.; Ramirez, F.; Maracek, J. J. Am. Chem. Soc. 1984, 106, 6877-6883.
19. Henchman, M.; Viggiano, A. A.; Paulson, J. F.; Freedman, A.; Wormhoudt, J. J. Am. Chem. Soc. 1985, 107, 1453-1455.
20. Roesky, H. W.; Ahlrichs, R.; Brode, S. Angew. Chem., Int. Ed. Engl. 1986, 25, 82-83.
21. Bourne, N.; Williams, A. J. Org. Chem. 1984, 49, 1200-1204.
22. Abell, K. W. Y.; Kirby, A. J. Tetrahedron Lett. 1986, 27, 1085-1088.
23. Cleland, W. W. Methods Enzymol. 1979, 63, 103-138.
24. Marcus, Y. Pure Appl. Chem. 1983, 55, 977-1021.
25. Pecoraro, V. L.; Hermes, J. D.; Cleland, W. W. Biochemistry 1984, 23, 5262-5271.
26. Sigel, R. K. O.; Song, B.; Sigel, H. J. Am. Chem. Soc. 1997, 119, 744-755.
27. Massoud, S. S.; Sigel, H. Inorg. Chem. 1988, 27, 1447-1453.
28. Herschlag, D.; Jencks, W. P. J. Am. Chem. Soc. 1987, 109, 4665-4674.