Solvent isotope effects in H2O-D2O mixtures (proton inventories) on serine-protease-catalyzed hydrolysis reactions. Influence of oxyanion hole interactions and medium effects

Journal of the American Chemical Society

Volumn 118, Issue 37, 1996, Pages 8802-8807

  Chang, T K ^b   Chiang, Y ^a   Guo, H X ^a   Kresge, A J ^a   Mathew, L ^a   Powell, M F ^b   Wells, J A ^b  

^a UNIVERSITY OF TORONTO   (Canada)

^b GENENTECH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SERINE PROTEINASE;

ARTICLE; ENZYME ACTIVITY; HYDROLYSIS; ISOTOPE LABELING; REACTION ANALYSIS;

EID: 0029789988     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9614326     Document Type: Article

References (41)

1. Kresge, A. J. Pure Appl. Chem. 1964, 8, 243-258.
2. 2O mixtures. Gross and Butler, however, derived only a special case of eq 1, that pertaining to the ionization of a monobasic acid, and the completely general relationship of eq 1 was not available until it first appeared in ref 3.
3. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1936, 32, 877-879. Gross, P.; Wischin, A. Trans. Faraday Soc. 1936, 32, 879-883. Gross, P.; Steiner, H.; Suess, H. Trans. Faraday Soc. 1936, 32, 883-899. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1938, 34, 351-356.
4. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1936, 32, 877-879. Gross, P.; Wischin, A. Trans. Faraday Soc. 1936, 32, 879-883. Gross, P.; Steiner, H.; Suess, H. Trans. Faraday Soc. 1936, 32, 883-899. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1938, 34, 351-356.
5. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1936, 32, 877-879. Gross, P.; Wischin, A. Trans. Faraday Soc. 1936, 32, 879-883. Gross, P.; Steiner, H.; Suess, H. Trans. Faraday Soc. 1936, 32, 883-899. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1938, 34, 351-356.
6. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1936, 32, 877-879. Gross, P.; Wischin, A. Trans. Faraday Soc. 1936, 32, 879-883. Gross, P.; Steiner, H.; Suess, H. Trans. Faraday Soc. 1936, 32, 883-899. Gross, P.; Steiner, H.; Krauss, F. Trans. Faraday Soc. 1938, 34, 351-356.
7. Hornell, J. C.; Butler, J. A. V. J. Chem. Soc. 1936, 1361-1366. Orr, W. J. C.; Butler, J. A. V. J. Chem. Soc. 1937, 330-335. Nelson, W. E.; Butler, J. A. V. J. Chem. Soc. 1938, 957-962.
8. Hornell, J. C.; Butler, J. A. V. J. Chem. Soc. 1936, 1361-1366. Orr, W. J. C.; Butler, J. A. V. J. Chem. Soc. 1937, 330-335. Nelson, W. E.; Butler, J. A. V. J. Chem. Soc. 1938, 957-962.
9. Hornell, J. C.; Butler, J. A. V. J. Chem. Soc. 1936, 1361-1366. Orr, W. J. C.; Butler, J. A. V. J. Chem. Soc. 1937, 330-335. Nelson, W. E.; Butler, J. A. V. J. Chem. Soc. 1938, 957-962.
10. Kreevoy, M. M.; Liang, T. M. J. Am. Chem. Soc. 1980, 102, 3315-3322. Cleland, W. W. Biochemistry 1992, 31, 317-319. Cleland, W. W.; Kreevoy, M. M. Science, 1994, 264, 1887-1890. Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930.
11. Kreevoy, M. M.; Liang, T. M. J. Am. Chem. Soc. 1980, 102, 3315-3322. Cleland, W. W. Biochemistry 1992, 31, 317-319. Cleland, W. W.; Kreevoy, M. M. Science, 1994, 264, 1887-1890. Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930.
12. Kreevoy, M. M.; Liang, T. M. J. Am. Chem. Soc. 1980, 102, 3315-3322. Cleland, W. W. Biochemistry 1992, 31, 317-319. Cleland, W. W.; Kreevoy, M. M. Science, 1994, 264, 1887-1890. Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930.
13. Kreevoy, M. M.; Liang, T. M. J. Am. Chem. Soc. 1980, 102, 3315-3322. Cleland, W. W. Biochemistry 1992, 31, 317-319. Cleland, W. W.; Kreevoy, M. M. Science, 1994, 264, 1887-1890. Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930.
14. For a recent review, see: Quinn, D. M.; Sutton, L. D. In Enzyme Mechanisms from Isotope Effects; Cook, P. F., Ed.; CRC Press: Boca Raton, FL, 1991; pp 73-126.
15. For a review, see: Venkatasubban, K. S.; Schowen, R. L. CRC Crit. Rev. Biochem. 1984, 17, 1-44.
16. Scholten, J. D.; Hogg, J. L.; Raushel, F. M. J. Am. Chem. Soc. 1988, 110, 8246-8247.
17. Braxton, S.; Wells, J. A. J. Biol. Chem. 1991, 266, 11797-11800.
18. McPhalen, C. A.; James, M. N. G. Biochemistry 1988, 27, 6582-6598.
19. Del Mar, E. G.; Largman, C.; Brodrick, J. W.; Geokas, M. C. Anal. Biochem. 1979, 99, 316-320.
20. Wells, J. A.; Cunnngham, B. C.; Graycar, T. P.; Estell, D. A. Phil. Trans. Roy. Soc. London A 1986, 317, 415-423.
21. (a) Albery, W. J.; Davies, M. H. J. Chem. Soc., Faraday Trans. II 1972, 68, 167-181.
22. (b) Albery, W. J. In Proton Transfer Reactions, Caldin, E. F., Gold, V., Ed.; Chapman and Hall: London, 1975, Chapter 9.
23. Chiang, Y.; Kresge, A. J.; Chang, T. K.; Powell, M. F.; Wells, J. A. J. Chem. Soc., Chem. Comm. 1995, 1587-1588.
24. Carter, P.; Wells, J. A. Proteins: Struct. , Funct., Genet. 1990, 7, 335-342.
25. Northrop, D. B. In Isotope Effects on Enzyme-Catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, MD, 1977; pp 122-152.
26. Supporting information; see paragraph at the end of this paper regarding availability.
27. (a) Bryan, P.; Pantoliano, M. W.; Quill, S. G.; Hsiao, H.-Y.; Poulos, T. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 3743-3745.
28. (b) Carter, P.; Wells, J. A. Nature 1988, 332, 564-568.
29. Gelb, R. I.; Schwartz, L. M.; Bradshaw, J. J.; Laufer, D. A. Bioorg. Chem. 1980, 9, 299-304.
30. Fernandez, L. P.; Hepler, L. G. J. Am. Chem. Soc. 1959, 81, 1783-1786.
31. Gelb, R. I.; Schwartz, L. M.; Cardelino, B.; Laufer, D. A. Anal. Biochem. 1980, 103, 362-368.
32. Carter, P.; Abrahamson, L.; Wells, J. A. Biochemistry 1991, 30, 6142-6148.
33. Kresge, A. J. J. Am. Chem. Soc. 1973, 95, 3065-3067.
34. Gold, V. Adv. Phys. Org. Chem. 1969, 7, 259-331. Kresge, A. J.; More O'Ferrall, R. A.; Powell, M. F. In Isotopes in Organic Chemistry; Vol. 7, Buncel, E., Lee, C. C., Eds.; Elsevier: New York, 1987, pp 177-273.
35. Gold, V. Adv. Phys. Org. Chem. 1969, 7, 259-331. Kresge, A. J.; More O'Ferrall, R. A.; Powell, M. F. In Isotopes in Organic Chemistry; Vol. 7, Buncel, E., Lee, C. C., Eds.; Elsevier: New York, 1987, pp 177-273.
36. M.
37. M proton inventories, and it therefore does not meet the criterion that transition state fractionation factors for the two kinds of proton inventory must be the same.
38. Arnett, E. M.; McKelvey, D. R. in Solute-Solvent Interactions; Coetzee, J. F., Ritchie, C. D., Eds.; Marcel Dekker: New York, 1969; pp 343-398.
39. Bender, M. L.; Komiyama, M. Cyclodextrin Chemistry; Springer-Verlag: Berlin, 1978. Bender, M. L. in Enzyme Mechanism; Page, M. I., Williams, A., Eds.; Royal Society of Chemistry: London, 1987: pp 56-76. Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
40. Bender, M. L.; Komiyama, M. Cyclodextrin Chemistry; Springer-Verlag: Berlin, 1978. Bender, M. L. in Enzyme Mechanism; Page, M. I., Williams, A., Eds.; Royal Society of Chemistry: London, 1987: pp 56-76. Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
41. Bender, M. L.; Komiyama, M. Cyclodextrin Chemistry; Springer-Verlag: Berlin, 1978. Bender, M. L. in Enzyme Mechanism; Page, M. I., Williams, A., Eds.; Royal Society of Chemistry: London, 1987: pp 56-76. Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.