Kinetic isotope effects of L-Dopa decarboxylase

Journal of the American Chemical Society

Volumn 133, Issue 12, 2011, Pages 4398-4403

  Lin, Yen Lin ^a   Gao, Jiali ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; COFACTORS; DECARBOXYLASES; DECARBOXYLATION REACTIONS; ENZYME ACTIVE SITES; FREE-ENERGY PERTURBATION METHODS; HYDROGEN KINETICS; KINETIC ISOTOPE EFFECTS; MICHAELIS COMPLEX; PATH INTEGRAL; PLP-DEPENDENT ENZYMES; PRIMARY CARBON; PROTONATED; PROTONATED SCHIFF BASE; SECONDARY PROTONS; TRANSITION STATE; UNCATALYZED REACTIONS;

AMINO ACIDS; CARRIER MOBILITY; ENZYMES; FREE ENERGY; FUNCTIONAL GROUPS; ISOTOPES; PERTURBATION TECHNIQUES; PROTONATION; PROTONS;

CARBOXYLATION;

AROMATIC LEVO AMINO ACID DECARBOXYLASE; CARBON 13; CARBOXYLIC ACID; ISOTOPE; OXIME; PYRIDOXAL 5 PHOSPHATE; SCHIFF BASE; WATER; ZALCITABINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DECARBOXYLATION; DRUG STABILITY; ENZYME ACTIVE SITE; KINETIC ISOTOPE EFFECT; KINETICS; MICHAELIS CONSTANT; NONHUMAN; PHASE TRANSITION; PROTON TRANSPORT; VALIDATION STUDY;

ANIMALS; BIOCATALYSIS; CRYSTALLOGRAPHY, X-RAY; DOPA DECARBOXYLASE; ISOTOPES; KIDNEY; KINETICS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; QUANTUM THEORY; SCHIFF BASES; SWINE;

EID: 79953031248     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja108209w     Document Type: Article

References (53)

1. Richard, J. P.; Amyes, T. L.; Crugeiras, J.; Rios, A. Curr. Opin. Chem. Biol. 2009, 13, 475
2. Toney, M. D. Arch. Biochem. Biophys. 2005, 433, 279
3. Frey, P. A.; Hegeman, A. D. Enzymatic Reaction Mechanisms; Oxford University Press: New York, 2007.
4. Lin, Y. L.; Gao, J. Biochemistry 2010, 49, 84
5. Sharif, S.; Denisov, G. S.; Toney, M. D.; Limbach, H.-H. J. Am. Chem. Soc. 2006, 128, 3375
6. Sharif, S.; Denisov, G. S.; Toney, M. D.; Limbach, H.-H. J. Am. Chem. Soc. 2007, 129, 6313
7. Sharif, S.; Huot, M. C.; Tolstoy, P. M.; Toney, M. D.; Jonsson, K. H. M.; Limbach, H.-H. J. Phys. Chem. B 2007, 111, 3869
8. Sharif, S.; Schagen, D.; Toney, M. D.; Limbach, H.-H. J. Am. Chem. Soc. 2007, 129, 4440
9. Hayashi, H.; Mizuguchi, H.; Kagamiyama, H. Biochemistry 1993, 32, 812
10. Hayashi, H.; Tsukiyama, F.; Ishii, S.; Mizuguchi, H.; Kagamiyama, H. Biochemistry 1999, 38, 15615
11. Nishino, J.; Hayashi, H.; Ishii, S.; Kagamiyama, H. J. Biochem. (Tokyo) 1997, 121, 604
12. Burkhard, P.; Dominici, P.; Borri-Voltattorni, C.; Jansonius, J. N.; Malashkevich, V. N. Nat. Struct. Biol. 2001, 8, 963
13. Minelli, A.; Charteris, A. T.; Voltattorni, C. B.; John, R. A. Biochem. J. 1979, 183, 361
14. Voltattorni, C. B.; Minelli, A.; Vecchini, P.; Fiori, A.; Turano, C. Eur. J. Biochem. 1979, 93, 181
15. Dixon, J. E.; Bruice, T. C. Biochemistry 1973, 12, 4762
16. Richard, J. P.; Amyes, T. L. Bioorg Chem 2004, 32, 354
17. Toth, K.; Richard, J. P. J. Am. Chem. Soc. 2007, 129, 3013
18. Major, D. T.; Nam, K.; Gao, J. J. Am. Chem. Soc. 2006, 128, 8114
19. Major, D. T.; Gao, J. J. Am. Chem. Soc. 2006, 128, 16345
20. Gao, J.; Xia, X. Science 1992, 258, 631
21. Gao, J.; Ma, S.; Major, D. T.; Nam, K.; Pu, J.; Truhlar, D. G. Chem. Rev. 2006, 106, 3188
22. Major, D. T.; Gao, J. J. Chem. Theory Comput. 2007, 3, 949
23. Gao, J.; Wong, K.-Y.; Major, D. T. J. Comput. Chem. 2008, 29, 514
24. Major, D. T.; Gao, J. J. Mol. Graph. Model. 2005, 24, 121
25. Major, D. T.; Garcia-Viloca, M.; Gao, J. J. Chem. Theory Comput. 2006, 2, 236
26. Major, D. T.; Heroux, A.; Orville, A. M.; Valley, M. P.; Fitzpatrick, P. F.; Gao, J. Proc. Natl. Acad. Sci. 2009, 106, 20734
27. Gao, J.; Wong, K.-Y.; Major, D. T.; Cembran, A.; Song, L.; Lin, Y.-L.; Fan, Y.; Ma, S. In Quantum Tunnelling in Enzyme-Catalysed Reactions; Allemann, R. K., Ed.; RSC Publishing: London, 2009; p 105.
28. Gao, J. In Rev. Comput. Chem.; Lipkowitz, K. B.; Boyd, D. B., Eds.; VCH: New York, 1995; Vol. 7, p 119.
29. Gao, J.; Amara, P.; Alhambra, C.; Field, M. J. J. Phys. Chem. A 1998, 102, 4714
30. Amara, P.; Field, M. J.; Alhambra, C.; Gao, J. Theor. Chem. Acc. 2000, 104, 336
31. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902
32. Gao, J. J. Am. Chem. Soc. 1995, 117, 8600
33. Wu, N.; Mo, Y.; Gao, J.; Pai, E. F. Proc. Natl. Acad. Sci. 2000, 97, 2017
34. Gao, J. Cur. Opin. Struct. Biol. 2003, 13, 184
35. Lill, S. O. N.; Gao, J.; Waldrop, G. L. J. Phys. Chem. B 2008, 112, 3149
36. Sicinska, D.; Truhlar, D. G.; Paneth, P. J. Am. Chem. Soc. 2005, 127, 5414
37. MacKerell, A. D., Jr.; Bashford, D.; Bellott, M.; Dunbrack, R. L.; Evanseck, J. D.; Field, M. J.; Fischer, S.; Gao, J.; Guo, H.; Ha, S.; Joseph-McCarthy, D.; Kuchnir, L.; Kuczera, K.; Lau, F. T. K.; Mattos, C.; Michnick, S.; Ngo, T.; Nguyen, D. T.; Prodhom, B.; Reiher, W. E., III; Roux, B.; Schlenkrich, M.; Smith, J. C.; Stote, R.; Straub, J.; Watanabe, M.; Wiorkiewicz-Kuczera, J.; Yin, D.; Karplus, M. J. Phys. Chem. B 1998, 102, 3586
38. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926
39. Nam, K.; Gao, J.; York, D. M. J. Chem. Theory Comput. 2005, 1, 2
40. Kumar, S.; Bouzida, D.; Swendsen, R. H.; Kollman, P. A.; Rosenberg, J. M. J. Comput. Chem. 1992, 13, 1011
41. Major, D. T.; York, D. M.; Gao, J. J. Am. Chem. Soc. 2005, 127, 16374
42. Jang, S.; Voth, G. A. J. Chem. Phys. 2000, 112, 8747
43. Schwieters, C. D.; Voth, G. A. J. Chem. Phys. 1999, 111, 2869
44. Sprik, M.; Klein, M. L.; Chandler, D. Phys. Rev. B 1985, 31, 4234
45. Hwang, J. K.; Warshel, A. J. Phys. Chem. 1993, 97, 10053
46. Pollock, E. L.; Ceperley, D. M. Phys. Rev. B 1984, 30, 2555
47. Chakrabarti, N.; Carrington, T., Jr.; Roux, B. Chem. Phys. Lett. 1998, 293, 209
48. Billeter, S. R.; Webb, S. P.; Agarwal, P. K.; Iordanov, T.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2001, 123, 11262
49. Kalyancker, G. D.; Snell, E. E. Biochemistry 1962, 1, 594
50. Snider, M. J.; Wolfenden, R. J. Am. Chem. Soc. 2000, 122, 11507
51. O'Leary, M. H. Acc. Chem. Res. 1988, 21, 450
52. Swanson, T.; Brooks, H. B.; Osterman, A. L.; O'Leary, M. H.; Phillips, M. A. Biochemistry 1998, 37, 14943
53. Pauling, L. C. The Nature of the Chemical Bond; 3 rd ed.; Cornell University Press: Ithaca, NY, 1960.