Divalent metal ion catalysis in the hydrolysis of phosphomonoesters. Hydrolysis of 2-(1,10-phenanthrolyl) phosphate

Journal of the American Chemical Society

Volumn 110, Issue 23, 1988, Pages 7790-7797

  Fife, Thomas H ^a   Pujari, Mahesh P ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CATALYSIS; ENZYMES; IONS; WATER;

ALKALINE PHOSPHATASE; METHYL PHOSPHATE; NUCLEOPHILIC PATHWAYS; PHENANTHROLYL; PHOSPHOMONOESTERS;

PHOSPHATES;

EID: 0024282848     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00231a033     Document Type: Article

References (55)

1. Stryer, L. Biochemistry, 2nd ed., W. H. Freeman: San Francisco, 1975.
2. Bruice, T. C.; Benkovic, S.; Bioorganic Mechanisms; W. A. Benjamin: New York, 1966; Vol. 2, and references therein.
3. Westheimer, F. H.; Acc. Chem. Res. 1968, 1, 70.
4. Cox, J. R.; Ramsay, O. B.; Chem. Rev. 1964, 64, 317.
5. Benkovic, S. J.; In Comprehensive Chemical Kinetics; Bamford, C. H., Tipper, C. F., Eds.; Elsevier: New York, 1972; Vol. 10.
6. Bunton, C. A.; Llewellyn, D. R.; Oldham, K. G.; Vernon, C. A. J. Chem. Soc. 1958, 3574.
7. Butcher, W. W.; Westheimer, F. H. J. Am. Chem. Soc. 1955, 77, 2420.
8. Kumamoto, J.; Westheimer, F. H. J. Am. Chem. Soc. 1955, 77, 2515.
9. Kirby, A. J.; Varvoglis, A. G. J. Am. Chem. Soc. 1967, 89, 415.
10. Milstien, S.; Fife, T. H. J. Am. Chem. Soc. 1967, 89, 5820.
11. Bourne, N.; Williams, A. J. Am. Chem. Soc. 1984, 106, 7591.
12. Skoog, M. T.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 7597.
13. Herschlag, D.; Jencks, W. P. J. Am. Chem. Soc. 1986, 108, 7938.
14. Ramirez, F.; Marecek, J.; Minore, J.; Srivastava, S.; le Noble, W. J. Am. Chem. Soc. 1986, 108, 348.
15. Benkovic, S. J.; Schray, K. J. In The Enzymes; Boyer, P. D., Ed,; Academic: New York, 1973; Vol. 8, p 201.
16. Reid, T. W.; Wilson, I. B.; In The Enzymes; Boyer, P. D., Ed., Academic: New York, 1971; Vol. 4.
17. Spiro, T. G. In Inorganic Biochemistry;; Eichhorn, G. L., Ed.; American Elsevier: New York, 1973; p 549.
18. Coleman, J. E.; Gettins, P.; Adv. Enzymol. Relat. Areas Mol. Biol. 1983, 55, 381.
19. O'Sullivan, W. J. In Inorganic Biochemistry; Eichhorn, G. L. Ed.; American Elsevier: New York, 1973; p 582. Mildvan, A. S. Adv. Enzymol. 1979, 49, 103.
20. Coleman, J. E.; Chlebowski, J. F. Advances in Inorganic Biochemistry; Eichhorn, G. L., Marzilli, L. G., Eds.; Elsevier: New York, 1979; Vol. 1.
21. Hofstetter, R.; Murakami, Y.; Mont, G.; Martell, A. E. J. Am. Chem. Soc. 1962, 84, 3041.
22. -. Hay, R. W.; Basak, A. K.; Pujari, M. P.; Perotti, A. J. Chem. Soc., Dalton Trans. 1986, 2029.
23. Benkovic, S. J.; Dunikoski, L., Jr. J. Am. Chem. Soc. 1971, 93, 1526.
24. Lloyd, G. J.; Cooperman, B. S. J. Am. Chem. Soc. 1971, 93, 4883.
25. Benkovic, S. J.; Miller, E. M. Bioinorg. Chem. 1972, 1, 107.
26. Murakami, Y.; Sunamoto, J. Bull. Chem. Soc. Jpn. 1971, 44, 1827.
27. Herschlag, D.; Jencks, W. P. J. Am. Chem. Soc. 1987, 109, 4665.
28. Halcrow, B. E.; Kermack, W. O. J. Chem. Soc. 1946, 155.
29. Claus, K.; Rund, J. V. Inorg. Chem. 1969, 8, 59.
30. Zacharias, D. E.; Case, F. H. J. Org. Chem. 1962, 27, 3878.
31. Bell, R. S.; Sutin, N. Inorg. Chem. 1962, 1, 359.
32. Holyer, R. H.; Hubbard, C. D.; Kettle, S. F. A.; Wilkins, R. G. Inorg. Chem. 1965, 4, 929.
33. Wilkens, R. G. Acc. Chem. Res. 1970, 3, 408.
34. Kirby, A. J.; Jencks, W. P. J. Am. Chem. Soc. 1965, 87, 3209.
35. Schaleger, L. L.; Long, F. A. Adv. Phys. Org. Chem. 1963, 1, 1.
36. Long, F. A.; Pritchard, J. G.; Stafford, F. E. J. Am. Chem. Soc. 1957, 79, 2362.
37. Bromilow, R. H.; Kirby, A. J. J. Chem. Soc., Perkin Trans. 2 1972, 149.
38. Jones, D. R.; Lindoy, L. F.; Sargeson, A. M. J. Am. Chem. Soc. 1983, 105, 7327.
39. Wells, M. A.; Rogers, G. A.; Bruice, T. C. J. Am. Chem. Soc. 1976, 98, 4336. Wells, M. A.; Bruice, T. C. J. Am. Chem. Soc. 1977, 99, 5341.
40. Hay, R. W.; Clark, C. R. J. Chem. Soc., Dalton Trans. 1977, 1866, 1993.
41. Fife, T. H.; Przystas, T. J.; Squillacote, V. L. J. Am. Chem. Soc. 1979, 101, 3017.
42. Fife, T. H.; Przystas, T. J. J. Am. Chem. Soc. 1982, 104, 2251.
43. Breslow, R.; McAllister, C. J. Am. Chem. Soc. 1971, 93, 7096.
44. Fife, T. H.; Przystas, T. J. J. Am. Chem. Soc. 1985, 107, 1041.
45. Groves, J. T.; Dias, R. M. J. Am. Chem. Soc. 1979, 101, 1033.
46. Groves, J. T.; Chambers, R. R., Jr. J. Am. Chem. Soc. 1984, 106, 630.
47. Fife, T. H.; Przystas, T. J. J. Am. Chem. Soc. 1986, 108, 4631.
48. Fife, T. H.; Pyzystas, T. J. J. Am. Chem. Soc. 1983, 105, 1638.
49. Breslow, R.; McClure, D. E.; Brown, R. S.; Eisenach, J. J. Am. Chem. Soc. 1975, 97, 194.
50. See also: Kirby, A. J.; Varvoglis, A. G. J. Chem. Soc. B 1968, 135. Rate constants for hydrolysis of phosphorylated pyridine and imidazole are given in ref 8a and 16.
51. Knowles, J. R. Annu. Rev. Biochem. 1980, 49, 877.
52. Williams, A.; Naylor, R. A. J. Chem. Soc. B 1971, 1973.
53. II in the enzyme active site with a phosphomonoester is structurally feasible: Sowadski, J. M.; Handschumacher, M. D.; Murthy, H. M. K.; Foster, B. A.; Wyckoff, H. W. J. Mol. Biol. 1985, 186, 417.
54. Otvos, J. D.; Alger, J. R.; Coleman, J. E.; Armitage, I. M. J. Biol. Chem. 1979, 254, 1778 and references therein.
55. For a mechanism of that type see: Cleland, W. W. Adv. Enzymol. Relat. Areas Mol. Biol. 1977, 45, 273.