Proton-Coupled Electron Transfer in Soybean Lipoxygenase

Journal of the American Chemical Society

Volumn 126, Issue 18, 2004, Pages 5763-5775

  Hatcher, Elizabeth ^a   Soudackov, Alexander V ^a   Hammes Schiffer, Sharon ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FREE ENERGY; IRON COMPOUNDS; ISOTOPES; KINETIC THEORY; QUANTUM THEORY;

IRON COFACTORS; MULTISTATE CONTINUUM THEORY; PROTON-COUPLED ELECTRON TRANSFER; REORGANIZATION ENERGIES;

ENZYMES;

DEUTERIUM; HYDROGEN; IRON; ISOTOPE; LIPOXYGENASE; PROTON;

ARTICLE; CATALYSIS; CONFORMATION; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; ENERGY; EQUILIBRIUM CONSTANT; KINETICS; MODEL; MOLECULAR INTERACTION; QUANTUM MECHANICS; SOYBEAN; TEMPERATURE DEPENDENCE; THEORY; VIBRATION;

ELECTRON TRANSPORT; ELECTRONS; GASES; IRON; KINETICS; LIGANDS; LIPOXYGENASE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROBABILITY; PROTEIN CONFORMATION; PROTONS; SOYBEANS; TEMPERATURE; THERMODYNAMICS; VIBRATION;

EID: 2442548491     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039606o     Document Type: Article

References (58)

1. Samuelsson, B.; Dahlen, S.-E.; Lindgren, J.; Rouzer, C. A.; Serhan, C. N. Science 1987, 237, 1171-1176.
2. Holman, T. R.; Zhou, J.; Solomon, E. L. J. Am. Chem. Soc. 1998, 120, 12564-12572.
3. Steele, V. E.; Holmes, C. A.; Hawk, E. T.; Kopelovich, L.; Lubet, R. A.; Crowell, J. A.; Sigman, C. C.; Kelloff, G. J. Cancer Epidemiol., Biomarkers Prev. 1999, 8, 467-483.
4. Rioux, N.; Castonguay, A. Carcilogenesis 1998, 19, 1393-1400.
5. Nie, D.; Hillman, G. G.; Geddes, T.; Tang, K.; Pierson, C.; Grignon, D. J.; Honn, K. V. Cancer Res. 1998, 58, 4047-4051.
6. Ghosh, J.; Myers, C. E. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 13182-13187.
7. Rickert, K. W.; Klinman, J. P. Biochemistry 1999, 38, 12218-12228.
8. Lewis, E. R.; Johansen, E.; Holman, T. R. J. Am. Chem. Soc. 1999, 121, 1395-1396.
9. Although the natural substrate for human lipoxygenase is arachidonic acid, it also reacts with linoleic acid.8
10. Glickman, M. H.; Klinman, J. P. Biochemistry 1995, 34, 14077-14092.
11. Lehnert, N.; Solomon, E. L. J. Biol. Inorg. Chem. 2003, 8, 294-305.
12. Knapp, M. J.; Rickert, K. W.; Klinman, J. P. J. Am. Chem. Soc. 2002, 124, 3865-3874.
13. Jonsson, T.; Glickman, M. H.; Sun, S.; Klinman, J. P. J. Am. Chem. Soc. 1996, 118, 10319-10320.
14. Glickman, M. H.; Wiseman, J. S.; Klinman, J. P. J. Am. Chem. Soc. 1994, 116, 793-794.
15. Hwang, C.-C.; Grissom, C. B. J. Am. Chem. Soc. 1994, 116, 795-796.
16. Knapp, M. J.; Seebeck, F. P.; Klinman, J. P. J. Am. Chem. Soc. 2001, 123, 2931-2932.
17. Soudackov, A.; Hammes-Schiffer, S. J. Chem. Phys. 1999, 111, 4672-4687.
18. Soudackov, A.; Hammes-Schiffer, S. J. Chem. Phys. 2000, 113, 2385-2396.
19. Hammes-Schiffer, S. Acc. Chem. Res. 2001, 34, 273-281.
20. Basilevsky, M. V.; Rostov, I. V.; Newton, M. D. Chem. Phys. 1998, 232, 189-199.
21. Newton, M. D.; Basilevsky, M. V.; Rostov, I. V. Chem. Phys. 1998, 232, 201-210.
22. Cukier, R. I. J. Phys. Chem. 1996, 100, 15428-15443.
23. Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369.
24. Mayer, J. M.; Hrovat, D. A.; Thomas, J. L.; Borden, W. T. J. Am. Chem. Soc. 2002, 124, 11142-11147.
25. μν is much less than the thermal energy) due to the small overlap between the dominant reactant and product hydrogen vibrational wave functions.
26. Soudackov, A. V.; Hatcher, E.; Hammes-Schiffer, S., to be submitted for publication.
27. Zhou, Z.; Khan, S. U. M. J. Phys. Chem. 1989, 93, 5292-5295.
28. Warshel, A. Computer Modeling of Chemical Reactions in Enzymes and Solutions: John Wiley & Sons: New York, 1991.
29. Lee, C.; Yang, W.; Parr, P. G. Phys. Rev. B 1988, 45, 785.
30. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
31. Dunning, J., T. H.; Hay, P. J. Modern Theoretical Chemistry; Plenum: New York, 1976; Vol. 3.
32. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1984, 82, 270.
33. 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
34. Borowski, T.; Krol, M.; Chruszcz, M.; Broclawik, E. J. Phys. Chem. B 2001, 105, 12212-12220.
35. Olson, M. A.; Reinke, L. T. Proteins: Struct., Funct., Genet. 2000, 38, 115-119.
36. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639-1662.
37. Tomchick, D. R.; Phan, P.; Cymbrowski, M.; Minor, W.; Holman, T. R. Biochemistry 2001, 40, 7509-7517.
38. Skrzypczak-Jankun, E.; Bross, R. A.; Carroll, R. T.; Dunham, W. R.; Funk, J. M. O. J. Am. Chem. Soc. 2001, 123, 10814-10820.
39. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361.
40. Kuntz, P. J.; Nemeth, E. M.; Polanyi, J. C.; Rosner, S. D.; Young, C. E. J. Chem. Phys. 1966, 44, 1168-1184.
41. Kim, Y.; Truhlar, D. G.; Kreevoy, M. M. J. Am. Chem. Soc. 1991, 113, 7837-7847.
42. Basilevsky, M. V.; Soudackov, A. V.; Vener, M. V. Chem. Phys. 1995, 200, 87-106.
43. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
44. Glasstone, S.; Laidler, K. J.; Eyring, H. The Theory of Rate Processes; McGraw-Hill: New York, 1941.
45. 2 during the PCET reaction.
46. Bu, Y.; Liu, S.; Song, X. Chem. Phys. Lett. 1994, 227, 121-125.
47. Iordano, N.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2002, 124, 4848-4856.
48. Kuznetsov, A. M.; Ulstrup, J. Can. Chem. 1999, 77, 1085-1096.
49. Wiseman, J. S. Biochemistry 1989, 28, 2106-2111.
50. Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458-7462.
51. Nelson, M. J. Biochemistry 1988, 27, 4273-4278.
52. Arnett, E. M.; Venkatasubramaniam, K. G. J. Org. Chem. 1983, 48, 1569-1574.
53. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
54. Wayner, D. D. M.; Parker, V. D. Acc. Chem. Res. 1993, 26, 287-294.
55. Bordwell, F. G. Pure Appl. Chem. 1977, 49, 963-968.
56. Scarrow, R. C.; Trimitsis, M. G.; Buck, C. P; Grove, G. N.; Cowling, R. A.; Nelson, M. J. Biochemistry 1994, 33, 15023-15035.
57. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450.
58. Clark, K. B.; Culshaw, P. N.; Griller, D.; Lossing, F. P.; Simoes, J. A. M.; Walton, J. C. J. Org. Chem. 1991, 56, 5535-5539.