Efficiency of Proton Transfer Catalysis in Models and Enzymes

Accounts of Chemical Research

Volumn 30, Issue 7, 1997, Pages 290-296

  Kirby, Anthony J ^a,b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b Department of Chemistry ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001461840     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar960056r     Document Type: Article

References (40)

1. Fersht, A. R. Enzyme Structure and Mechanism, 2nd ed.; Freeman: New York, 1985.
2. Kirby, A. J. Philos. Trans. R. Soc. (London), Ser. A 1993, 345, 67.
3. Kirby, A. J. Angew. Chem. 1996, 35, 707-724.
4. Some, e.g. electrocyclic, reactions which do not involve active site functional groups directly in catalysis do not involve this sort of interaction. It is however fundamental to reactions in which strong σ-bonds are made and broken: and an essential part of catalysis for intrinsically slow reactions, where the enzyme has to be particularly efficient.
5. Wolfenden, R. Science 1994, 267, 90-93.
6. Dalby, K. N.; Kirby, A. J.; Hollfelder, F. J. Chem. Soc., Perkin Trans. 2 1993, 1269.
7. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183-278.
8. Jencks, W. P. Adv. Enzymol. 1975, 37, 219.
9. Menger, F. M. Acc. Chem. Res 1985, 18, 28-33.
10. Kirby, A. J.; Lancaster, P. W. J. Chem. Soc., Perkin Trans. 2, 1972, 1206.
11. Evans, C. M.; Kirby, A. J. J. Chem. Soc., Perkin Trans. 2 1984, 1269.
12. Buffet, C.; Lamaty, G. Recl. Trav. Chim. Pays-Bas 1976, 95, 1.
13. Hermans, J.; Leach, S. J.; Scheraga, H. A. J. Am. Chem. Soc., 1963, 85, 1390-1395.
14. Awwal, A.; F. Hibbert J. Chem. Soc., Perkin Trans. 2, 1977.
15. Kirby, A. J.; Percy, J. M. J. Chem. Soc., Perkin Trans. 2 1989, 907-912.
16. Kirby, A. J.; Parkinson, A. J. Chem. Soc., Chem. Commun. 1994, 707-708.
17. Craze, G.-A.; Kirby, A. J. J. Chem. Soc., Perkin Trans. 2, 1978, 354.
18. As a rough guide, hydrolysis reactions of methoxymethyl, tetrahydropyranyl, and benzaldehyde acetals are faster than those of the corresponding glucopyranosides by 4, 6-7, and 9-10 orders of magnitude, respectively.
19. Brown, C. J.; Kirby, A. J. J. Chem. Soc., Chem. Commun. 1996, 2355-2356.
20. Brown, C. J.; Kirby, A. J. J. Chem. Soc., Perkin Trans. 2 1997, in press.
21. Jensen, J. L.; Herold, L. R.; Lenz, P. A.; Trusty, S.; Sergi, V.; Bell, K.; Rogers, P. J. Am. Chem. Soc. 1979, 101, 4672-4677.
22. Landro, J. A.; Gerlt, J. A.; Kozarich, J. W.; Koo, C. W.; Shah, V. J.; Kenyon, G. L.; Neidhart, D. J.; Fujit, S.; Clifton, J. R.; Petsko, G. A. Biochemistry 1994, 33, 635-643.
23. Amyes, T. L.; Kirby, A. J. J. Am. Chem. Soc. 1988, 110, 6505-6514.
24. In this reaction, the intermediate 22 has the remarkable property of being protonated by water to give the product 23 of anti addition but by protonated amines to form the syn diastereoisomer. This is may be a function of the short lifetime of the intermediate, but the intrinsic chemistry is still not properly understood.
25. Kirby, A. J.; O'Carroll, F. J. Chem. Soc., Perkin Trans. 2 1994, 649-655.
26. Chiang, Y.; Kresge, A. J.; Young, C. I. Can. J. Chem. 1978, 56, 541.
27. Kirby, A. J.; Williams, N. H. J. Chem. Soc., Perkin Trans. 2 1994, 643-648.
28. Kresge, A. J. Acc. Chem. Res. 1990, 23, 43.
29. Thorn, S. N.; Daniels, R. G.; Auditor, M.-T. M.; Hilvert, D. N. Nature (London) 1995, 373, 228-230.
30. Casey, M. L.; Kemp, D. S.; Paul, K. G.; Cox, D. D. J. Org. Chem. 1973, 38, 2294-2301.
31. Kemp, D. S.; Casey, M. L. J. Am. Chem. Soc. 1973, 95, 6670-6680.
32. Kemp, D. S.; Cox, D. D.; Paul, K. G. J. Am. Chem. Soc. 1975, 97, 7312-7318.
33. Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. Nature (London) 1996, 383, 60-63.
34. Reymond, J. L.; Janda, K. D.; Lerner, R. A. Angew. Chem. 1991, 30, 1711-1713.
35. Fife, T. H.; Brod, L. H. J. Am. Chem. Soc. 1970, 92, 1681.
36. Blériot, Y.; Genre-Grandpierre, A.; Dintinger, T.; Tellier, C. Bioorg. Med. Chem. Lett. 1995, 5, 2655.
37. Genre-Grandpierre, A.; Loirat, M.-J.; Blanchard, D.; Hodgson, D. R. W.; Hollfelder, F.; Kirby, A. J.; Tellier, C. Bioorg. Med. Chem. Lett., submitted for publication.
38. It is important to stress at this point that the great majority of proteins do not catalyse the Kemp elimination!
39. Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568.
40. Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890.