Mechanisms of Thiamine-Catalyzed Reactions. A Kinetic Analysis of the Decarboxylation of Pyruvate by 3,4-Dimethylthiazolium Ion in Water and Ethanol

Journal of the American Chemical Society

Volumn 92, Issue 19, 1970, Pages 5707-5716

  Crosby, John ^a   Lienhard, Gustav E ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; DEUTERIUM; HYDROGEN; PYRUVIC ACID DERIVATIVE; THIAMINE; THIAZOLE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; KINETICS;

CATALYSIS; DEUTERIUM; ETHANOL; HYDROGEN; KINETICS; PYRUVATES; THIAMINE; THIAZOLES; WATER;

EID: 0014959829     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00722a027     Document Type: Article

References (45)

1. L. O. Krampitz (Ann. Rev. Biochem., 38, 213 (1969)) thoroughly reviews the enzymatic and model reactions.
2. R. Breslow and E. McNelis, J. Amer. Chem. Soc., 81, 3080
3. P. Haake, L. P. Bauscher, and W. B. Miller, J. Amer. Chem. Soc., 91, 1113 (1969)
4. J. Ullrich and A. Mannschreck, Biochim. Biophys. Acta, 115, 46 (1966).
5. W. Hafferl, R. Lundin, and L. L. Ingraham, Biochemistry, 2, 1298 (1963).
6. J. Crosby, R. Stone, and G. E. Lienhard, J. Amer. Chem. Sac, 92, 2891 (1970).
7. pD = reading of pH meter + 0.4; P. K. Glasoe and F. A. Long, J. Phys. Chem., 64, 188 (1960).
8. H. H. Strain, J. Amer. Chem. Soc., 57, 760 (1935).
9. M. Becker and H. Strehlow, Ber. Bunsenges. Phys. Chem., 64, 813 (1960).
10. P. Greenzaid, Z. Luz, and D. Samuel, J. Amer. Chem. Soc., 89, 749 (1967).
11. H. O. Spivey and T. Shedlovsky, J. Phys. Chem., 71, 2171 (1967).
12. E. Grunwald and B. J. Berkowitz, J. Amer. Chem. Soc., 73, 4939 (1951).
13. G. Briere, B. Crochon, and N. Felici, C. R. Acad. Sci., 254, 4458 (1962).
14. H. S. Harned and B. B. Owen, “The Physical Chemistry of Electrolyte Solutions,” 3rd ed, Reinhold, New York, N. Y., 1958, pp 593–594.
15. G. Briere, N. Felici, and E. Plot, C. R. Acad. Sci., 255, 107 (1962).
16. A. A. Frost and R. G. Pearson, “Kinetics and Mechanism,” 2nd ed, Wiley, New York, N. Y., 1961, pp 186–187.
17. G. D. Maier and D. E. Metzler, J. Amer. Chem. Soc., 79, 4386 (1957).
18. E. Yatco-Manzo, F. Roddy, R. G. Yount, and D. E. Metzler, J. Biol. Chem., 234, 733 (1959).
19. R. G. Yount and D. E. Metzler, J. Biol. Chem., 234, 738 (1959).
20. G. E. Lienhard and D. Packard, unpublished results.
21. M. R. Wright, J. Chem. Soc B, 548 (1968).
22. E. J. NcNelis, Ph.D. Thesis, Columbia University, New York, N. Y., 1960.
23. R. P. Bell and A. T. Kuhn, Trans. Faraday Soc., 59, 1789 (1963).
24. M. Eigen, Angew. Chem. Int. Ed. Engl., 3, 1 (1964).
25. G. E. Lienhard, J. Amer. Chem. Soc., 88, 5642 (1966).
26. G. E. Lienhard and W. P. Jencks, J. Amer. Chem. Soc., 87, 3863 (1965).
27. H. Goldschmidt and E. Mathiesen, Z. Phys. Chem. Stoechiom. Verwandschaftslehre, 119, 439 (1926).
28. R. P. Bell, Advan. Phys. Org, Chem., 4, 15 (1966).
29. P. Ballinger and F. A. Long, J. Amer. Chem. Soc., 82, 795 (1960).
30. M. Charton, J. Org. Chem., 29, 1222 (1964).
31. R. P. Bell, “The Proton in Chemistry,” Cornell University Press, Ithaca, N. Y., 1959, Chapter IV.
32. See ref 14, p 756.
33. G. S. Hammond, J. Amer. Chem. Soc., 77, 334 (1955).
34. C. S. Miller, J. M. Sprague, and L. O. Krampitz, Ann. N. Y. Acad. Sci., 98, 401 (1962).
35. L. O. Krampitz and R. Votaw, Methods Enzymol, 9, 65 (1966).
36. W. J. Svirbely and J. F. Roth, J. Amer. Chem. Soc., 75, 3107 (1953).
37. See ref 16, pp 335–350.
38. J. Hine, J. G. Houston, and J. H. Jensen, J. Org. Chem., 30, 1184 (1965), and references therein.
39. J. Ullrich, J. H. Wittorf, and C. J. Gubler, Biochim. Biophys. Acta, 113, 595 (1966).
40. E. F. Caldin and G. Long, J. Chem. Soc., 3737 (1954).
41. F. Franks and D. J. G. Ives, Quart. Rev., Chem. Soc., 20, 1 (1966).
42. J. Ullrich and A. Mannshreck, Eur. J. Biochem., 1, 110 (1967).
43. J. J. Mieyal, R. G. Votaw, L. O. Krampitz, and H. Z. Sable, Biochim. Biophys. Acta, 141, 205 (1967).
44. C. Tanford, Advan. Protein Chem., 17, 111 (1962).
45. J. Steinhardt and S. Beychok, Proteins, 2, 223 (1964).