Acid-Base Catalysis of the Elimination and Isomerization Reactions of Triose Phosphates

Journal of the American Chemical Society

Volumn 106, Issue 17, 1984, Pages 4926-4936

  Richard, John P ^a  

^a FOX CHASE CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS - ISOMERIZATION;

CATALYSIS;

GLYCERALDEHYDE 3 PHOSPHATE;

DIHYDROXYACETINEPHOSPHATE; NONHUMAN;

EID: 0021471746     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00329a050     Document Type: Article

References (75)

1. Hall, A.; Knowles, J. R. Biochemistry 1975, 14, 4348.
2. Bonsignore, A.; Leoncini, G.; Siri, A.; Ricci, D. Ital. J. Biochem. 1973, 22, 131.
3. Iyengar, R.; Rose, I. A. J. Am. Chem. Soc. 1983, 105, 3301.
4. Noltmann, E. A. In “The Enzymes”, Boyer, P. D., Ed.; Academic Press: New York, 1972; Vol. 6, pp 271–354.
5. Hopper, D. J.; Cooper, R. A. Biochem. J. 1972,128, 321.
6. Tsai, P. K.; Gracy, R. W. J. Biol. Chem. 1976, 251, 364.
7. Cooper, R. A. Eur. J. Biochem. 1974, 44, 81.
8. Summers, M. C.; Rose, I. A. J. Am. Chem. Soc. 1977, 99, 4475.
9. Glynn, I. M.; Chappell, J. B. Biochem. J. 1964, 90, 147.
10. Rose, Z. B.; Pizer, L. I. J. Biol. Chem. 1968, 243, 4806.
11. Berenblum, I.; Chain, E. Biochem. J. 1938, 32, 295.
12. Plaut, B.; Knowles, J. R. Biochem. J. 1972, 129, 311.
13. Lapworth, A. J. Chem. Soc. 1904, 30.
14. Jones, J. R. “The Ionization of Carbon Acids”; Academic Press: London, 1973.
15. Fedor, L. R. J. Am. Chem. Soc. 1967, 89, 4479.
16. Fedor, L. R. J. Am. Chem. Soc. 1969, 91, 908.
17. Cavestri, R. C.; Fedor, L. R. J. Am. Chem. Soc. 1970, 92, 4610.
18. Fedor, L. R.; Glave, W. R. J. Am. Chem. Soc. 1971, 93, 985.
19. Jencks, W. P. Chem. Soc. Rev. 1981,10, 345.
20. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161.
21. Putnam, S. J.; Coulson, A. F. W.; Farley, I. R. T.; Riddleston, B.; Knowles, J. R. Biochem. J. 1972, 129, 301.
22. Rose, I. A.; O'Connell, E. L. J. Biol. Chem. 1969, 244, 126.
23. Bell, R. P. “The Proton in Chemistry”; 2nd ed.; Cornell University Press: Ithaca, New York, 1973; p 150.
24. Wilde, J.; Hunt, W.; Hupe, D. J. J. Am. Chem. Soc. 1977, 99, 8319.
25. Motiu-DeGrood, R.; Hunt, W.; Wilde, J.; Hupe, D. J. J. Am. Chem. Soc. 1979, 101, 2182.
26. Keeffe, J. R.; Jencks, W. P. J. Am. Chem. Soc. 1983, 105, 265.
27. Hand, E. S.; Jencks, W. P. J. Am. Chem. Soc. 1975, 97, 6221.
28. Reynolds, S. J.; Yates, D. W.; Pogson, C. I. Biochem. J, 1971,122, 285.
29. Trentham, D. R.; McMurray, C. H.; Pogson, C. I. Biochem. J. 1969, 114, 19.
30. Bell, R. P.; Onwood, D. P. Trans. Faraday Soc. 1962, 58, 1557.
31. Funderburk, L. H.; Aldwin, L.; Jencks, W. P. J. Am. Chem. Soc. 1978. 100, 5444.
32. Bell, R. P.; Evans, P. G. Proc. R. Soc. London, Ser. A 1966, 291, 297.
33. Emly, M.; Leussing, D. L. J. Am. Chem. Soc. 1981, 103, 628.
34. Bell, R. P.; Fluendy, A. D. Trans. Faraday Soc. 1963, 59, 1623.
35. Coward, J. K.; Bruice, T. C. J. Am. Chem. Soc. 1969, 91, 5339.
36. Gandour, R. D. Tetrahedron Lett. 1974, 295.
37. Bell, R. P.; Lidwell, O. M. Proc. R. Soc. London, Ser. A 1949,176, 88.
38. Hupe, D. J.; Wu, D. J. Am. Chem. Soc. 1977, 99, 7653.
39. Jencks, D. A.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 7948.
40. Hupe, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 451.
41. Thibblen, A. J. Am. Chem. Soc. 1984, 106, 183.
42. Jencks, W. P.; Brant, S. R.; Gandler, J. R.; Fendrich, G.; Nakamura, C. J. Am. Chem. Soc. 1982, 104, 7045.
43. Veech, R. L.; Raijman, L.; Dalziel, K.; Krebs, H. A. Biochem. J. 1969, 115, 837.
44. Hegarty, A. F.; Jencks, W. P. J. Am. Chem. Soc. 1975, 97, 7188.
45. Jencks, W. P. J. Am. Chem. Soc. 1972, 94, 4731.
46. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4689.
47. Crosby, J.; Stirling, C. J. M. J. Chem. Soc. B 1970, 679.
48. Ogata, Y.; Sawaki, Y.; Isono, M. Tetrahedron 1970, 26, 3045.
49. Friedman, M.; Cavins, J. F.; Wall, J. S. J. Am. Chem. Soc. 1965, 87, 3672.
50. Chiang, Y.; Kresge, A. J.; Tang, Y. S.; Wirz, J. J. Am. Chem. Soc. 1984, 106, 460.
51. Thomas, P. J.; Stirling, C. J. M. J. Chem. Soc., Perkins Trans. 2 1977, 1909.
52. Hine, J. In “Structural Effects on Equilibria in Organic Chemistry”; Wiley-Interscience: New York, 1975; p 181.
53. Hine, J.; Langford, P. B. J. Am. Chem. Soc. 1956, 78, 5002.
54. Hine, J.; Dalsin, P. D. J. Am. Chem. Soc. 1972, 94, 6998.
55. Thibblin, A.; Bengtssonn, S.; Ahlberg, P. J. Chem. Soc., Perkins Trans. 2 1977, 1569.
56. Thibblin, A.; Ahlberg, P. J. Am. Chem. Soc. 1979, 101, 7311.
57. Thibblin, A.; Ahlberg, P. J. Am. Chem. Soc. 1977, 99, 7926.
58. Eigen, M. Angew. Chem, Int. Ed. Engl. 1964, 3.
59. Alber, T.; Banner, D. W.; Bloomer, A. C.; Petsko, G. A.; Phillips, D.; Rivers, P. S.; Wilson, I. A. Philos. Trans, R. Soc. London, Ser. B 1981, 293, 159.
60. Iyengar, R.; Rose, I. A. Biochemistry 1981, 20, 1223.
61. Davies, C. S. “Ion Association”; Butterworths: London, 1962; pp 77–87.
62. Jencks, W. P. Acc. Chem. Res. 1976, 9, 425.
63. Rose, I. A.; Iyengar, R. Biochemistry 1982, 21, 1591.
64. Schray, K. J.; O'Connell, E. L.; Rose, I. A. J. Biol. Chem. 1973, 248, 2214.
65. Waley, S. J. Biochem. J. 1972, 126, 255.
66. Wolfenden, R. Biochemistry 1970, 9, 3404.
67. Johnson, L. N.; Wolfenden, R. J. Mol. Biol. 1970, 47, 93.
68. Hartman, F. C.; LaMuraglia, G. M.; Tomozawa, Y.; Wolfenden, R. Biochemistry 1975, 14, 5274.
69. Wolfenden, R. In “Antimetabolites in Biochemistry Biology and Medicine”; Skoda, J., Langen, P., Eds.; Pergamon Press: Oxford, 1979; Vol. 57, pp 151–160.
70. Belasco, J. G.; Knowles, J. R. Biochemistry 1980, 19, 472.
71. Webb, M. R.; Knowles, J. R. Biochem. J. 1974, 141, 589.
72. Jencks, W. P. In “Advances in Enzymology”; Meister, A., Ed.; John Wiley and Sons: New York, 1975; Vol. 43, pp 219–410.
73. Jencks, W. P. In “Molecular Biology, Biochemistry and Biophysics”; Chapeville, F., Haenni, A. L., Eds.; Springer-Verlag: New York, 1980; Vol. 32, pp 3–25.
74. Albery, W. J.; Knowles, J. R. Biochemistry 1976, 15, 5627.
75. Albery, W. J.; Knowles, J. R. Acc. Chem. Res. 1977, 10, 105.