Toward a consistent mechanism for diol dehydratase catalyzed reactions: An application of the partial-proton-transfer concept

Journal of the American Chemical Society

Volumn 121, Issue 24, 1999, Pages 5700-5704

  Smith, David M ^a   Golding, Bernard T ^b   Radom, Leo ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; COBAMAMIDE; DIOL DEHYDRATASE; ETHYLENE GLYCOL; HYDROLYASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENZYME ACTIVITY; ENZYME SUBSTRATE COMPLEX; PROTON TRANSPORT;

EID: 0033597609     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990209g     Document Type: Article

References (37)

1. 12; Dolphin, D., Ed.; J Wiley & Sons: New York, 1982; Vol. 2, p 233.
2. 12; Dolphin, D., Ed.; J Wiley & Sons: New York, 1982; Vol. 2, p 233.
3. 12; Dolphin, D., Ed.; J Wiley & Sons: New York, 1982; Vol. 2, p 233.
4. 12; Dolphin, D., Ed.; J Wiley & Sons: New York, 1982; Vol. 2, p 233.
5. See, for example: (a) Finke, R. G.; Schiraldi, D. A.; Mayer, B. J. Coord. Chem. Rev. 1984, 54, 1-22. (b) Hartmanis, M. G. N.; Stadtman, T. C. Proc. Natl. Acad. Sci. 1987, 84, 76-79. (c) Golding, B. T. Chem. Br. 1990, 26, 950-954.
6. See, for example: (a) Finke, R. G.; Schiraldi, D. A.; Mayer, B. J. Coord. Chem. Rev. 1984, 54, 1-22. (b) Hartmanis, M. G. N.; Stadtman, T. C. Proc. Natl. Acad. Sci. 1987, 84, 76-79. (c) Golding, B. T. Chem. Br. 1990, 26, 950-954.
7. See, for example: (a) Finke, R. G.; Schiraldi, D. A.; Mayer, B. J. Coord. Chem. Rev. 1984, 54, 1-22. (b) Hartmanis, M. G. N.; Stadtman, T. C. Proc. Natl. Acad. Sci. 1987, 84, 76-79. (c) Golding, B. T. Chem. Br. 1990, 26, 950-954.
8. For a recent review, see: Golding, B. T.; Buckel, W. In Comprehensive Biological Catalysis; Sinnott, M. L., Ed.; Academic Press: London, 1997; Vol. III, pp 239-259.
9. 2a,4b
10. (b) See, for example: Livingstone, R.; Zeldes, H. J. Am. Chem. Soc. 1966, 88, 4333-4336.
11. 12 and Intrinsic Factor; Zagalak, B., Friedrich, W., Eds.; W de Gruyter: Berlin, 1979; pp 389-410.
12. (a) Rétey, J.; Umani-Ronchi, A.; Seibl, J.; Arigoni, D. Experientia 1966, 22, 502.
13. (b) Rétey, J.; Robinson, J. A. In Stereospecificity in Organic Chemistry and Enzymology; Ebel, H. F., Ed.; Verlag Chemie: Weinheim, 1982; pp 185-207.
14. (a) George, P.; Glusker, J. P.; Bock, C. W. J. Am. Chem. Soc. 1995, 117, 10131-10132.
15. (b) George, P.; Glusker, J. P.; Bock, C. W. J. Am. Chem. Soc. 1997, 119, 7065-7074.
16. (a) Greenberg, A.; Liebman, J. F. In Energetics of Organic Free Radicals; Simoes, J. A. M., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional: London, 1996; Vol. 4, pp 224-294.
17. (a) Golding, B. T.; Radom, L. J. Chem. Soc., Chem. Commun. 1973, 939-941.
18. (b) Golding, B. T.; Radom, L. J. Am. Chem. Soc. 1976, 98, 6331-6338.
19. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
20. Gaussian 94, Revision E.2: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
21. Gaussian 98, Revision A.6: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.
22. MOLPRO 97 is a package of ab initio programs written by H.-J. Werner and P. J. Knowles with contributions from J. Almlof, R. D. Amos, A. Berning, D. L. Cooper, M. J. O. Deegan, A. J. Dobbyn, F. Eckert, S. T. Elbert, C. Hampel, R. Lindh, W. A. Lloyd, W. Meyer, A. Nickless, K. Peterson, R. Pitzer, A. J. Stone, P. R. Taylor, M. E. Mura, P Pulay, M. Schütz, H. Stoll, and T. Thorsteinsson.
23. Mayer, P. M.; Parkinson, C. J.; Smith, D. M.; Radom, L. J. Chem. Phys. 1998, 108, 604-615.
24. (a) Smith, D. M.; Nicolaides, A.; Golding, B. T.; Radom, L. J. Am. Chem. Soc. 1998, 120, 10223-10233.
25. (b) Smith, D. M.; Golding, B. T.; Radom, L. J. Am. Chem. Soc. 1999, 121, 1037-1044.
26. (c) Smith, D. M.; Golding, B. T.; Radom, L. J. Am. Chem. Soc. 1999, 121, 1383-1384.
27. (a) Smith, B. J.; Radom, L. J. Phys. Chem. 1995, 99, 6468-6471.
28. (b) Curtiss, L. A.; Redfern, P. C.; Smith, B. J.; Radom, L. J. Chem. Phys. 1996, 104, 5148-5152.
29. (a) Parkinson, C. J.; Mayer, P. M.; Radom, L. Theor. Chem. Acc., in press.
30. (b) Parkinson, C. J.; Mayer, P. M.; Radom, L. To be published.
31. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
32. Finke, R. G.; Schiraldi, D. A. J. Am. Chem. Soc. 1983,105, 7605-7617.
33. G2 calculated proton affinities at 0 K are taken from Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885-4888.
34. Buckel, W.; Golding, B. T. FEMS Microb. Rev. 1998, 22, 523-541.
35. Smith, D. M.; Golding, B. T.; Radom, L. Work in progress.
36. 12-Proteins; Krautler, B., Arigoni, D., Golding, B. T., Eds.; Wiley-VCH: Weinheim, 1998; pp 321-331.
37. (b) Siegbahn, P. E. M. J. Am. Chem. Soc. 1998, 120, 8417-8429.