A proficient enzyme revisited: The predicted mechanism for orotidine monophosphate decarboxylase

Science

Volumn 276, Issue 5314, 1997, Pages 942-945

  Lee, Jeehiun K ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OROTIDINE 5' PHOSPHATE DECARBOXYLASE;

ARTICLE; DECARBOXYLATION; ENERGY TRANSFER; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME MECHANISM; PRIORITY JOURNAL;

BARBITURATES; BINDING SITES; CATALYSIS; DECARBOXYLATION; ENZYME INHIBITORS; HYDROGEN-ION CONCENTRATION; KINETICS; OROTIDINE-5'-PHOSPHATE DECARBOXYLASE; PROTONS; THERMODYNAMICS; URIDINE MONOPHOSPHATE;

EID: 0030912339     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.276.5314.942     Document Type: Article

References (34)

1. A. Radzicka and R. Wolfenden, Science 267, 90 (1995).
2. R. W. McClard, M. J. Black, L. R. Livingstone, M. E. Jones, Biochemistry 19, 4699 (1980).
3. T. C. Bruice and S. Benkovic, in Bioorganic Mechanisms (Benjamin, New York, 1966), vol. 2, pp. 188-194.
4. M. L. Bender, in Mechanisms of Homogeneous Catalysis from Protons to Proteins (Wiley-Interscience, New York, 1971), pp. 165-175 and 586-594.
5. P. Beak and B. Siegel, J. Am. Chem. Soc. 98, 3601 (1976).
6. S. A. Acheson, J. B. Bell, M. E. Jones, R. Wolfenden, Biochemistry 29, 3198 (1990).
7. J. A. Smiley, P. Paneth, M. H. O'Leary, J. B. Bell, M. E. Jones, ibid. 30, 6216 (1991).
8. H. L. Levine, R. S. Brody, F. H. Westheimer, ibid. 19, 4993 (1980).
9. J. A. Smiley and S. J. Benkovic, Proc. Natl. Acad. Sci. U.S.A. 91, 8319 (1994).
10. J. B. Bell, M. E. Jones, C. W. J. Carter, Proteins 9, 143 (1991).
11. Attempts to obtain the crystal structure of ODCase are underway (C. Carter, personal communication).
12. J. A. Smiley and M. E. Jones, Biochemistry 31, 12162 (1992).
13. J. A. Smiley and S. J. Benkovic, J. Am. Chem. Soc. 117, 3877 (1995).
14. R. B. Silverman and M. P. Groziak, ibid. 104, 6434 (1982).
15. K. Shostak and M. E. Jones, Biochemistry 31, 12155 (1992).
16. Gaussian 94, revision B.3 (M. J. Frisch et al., Gaussian, Inc., Pittsburgh, PA, 1995). RHF, MP2, and basis sets are described by W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople [Ab Initio Molecular Orbital Theory (Wiley, New York, 1986)]. Density functional theory (Becke3LYP) is described by W. Kohn, A. D. Becke, and R. G. Parr [J. Phys. Chem. 100, 12974 (1996)].
17. Gaussian 94, revision B.3 (M. J. Frisch et al., Gaussian, Inc., Pittsburgh, PA, 1995). RHF, MP2, and basis sets are described by W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople [Ab Initio Molecular Orbital Theory (Wiley, New York, 1986)]. Density functional theory (Becke3LYP) is described by W. Kohn, A. D. Becke, and R. G. Parr [J. Phys. Chem. 100, 12974 (1996)].
18. Gaussian 94, revision B.3 (M. J. Frisch et al., Gaussian, Inc., Pittsburgh, PA, 1995). RHF, MP2, and basis sets are described by W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople [Ab Initio Molecular Orbital Theory (Wiley, New York, 1986)]. Density functional theory (Becke3LYP) is described by W. Kohn, A. D. Becke, and R. G. Parr [J. Phys. Chem. 100, 12974 (1996)].
19. ++ is for 0 K.
20. D. Lavorato et l., J. Am. Chem. Soc. 118, 11898 (1996), and references therein.
21. R. Kluger, Chem. Rev. 87, 863 (1987).
22. D. Kern et al., Science 275, 67 (1997).
23. A. J. Arduengo III et al., J. Am. Chem. Soc. 116, 6812 (1994), and references therein.
24. R. Wagner and W. von Philipsborn, Helv. Chim. Acta 53, 299 (1970).
25. S. G. Lias et al., J. Phys. Chem. Ref. Data 17, (suppl. no. 1) (1988).
26. a of protonated orotate to be ∼1.5.
27. J. A. Dean, in Lange's Handbook of Chemistry (McGraw-Hill, San Francisco, CA, 1992), pp. 8.19-8.71.
28. W. P. Jencks, J. Am. Chem. Soc. 94, 4731 (1972).
29. M. K. Gilson and B, H. Honig, Biopolymers 25, 2097 (1986).
30. G. King, F. S. Lee, A. Warshel, J. Chem. Phys. 95, 4366 (1991).
31. A. Warshel and J. Åqvist, Annu. Rev. Biophys. Biophys. Chem. 20, 267 (1991).
32. T, Simonson and C. L. Brooks III, J. Am. Chem. Soc. 118, 8452 (1996).
33. ++ values in solution.
34. We are grateful to NSF and NIH (postdoctoral fellowship to J.K.L.) for financial support of this work and to the UCLA Office of Academic Computing and the National Center for Supercomputing Applications for computational resources.