Proton-coupled electron transfer in a biomimetic peptide as a model of enzyme regulatory mechanisms

Journal of the American Chemical Society

Volumn 129, Issue 14, 2007, Pages 4393-4400

  Sibert, Robin ^a   Josowicz, Mira ^a   Porcelli, Fernando ^b,c   Veglia, Gianluigi ^b   Range, Kevin ^d   Barry, Bridgette A ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c UNIVERSITY OF TUSCIA   (Italy)

^d LOCK HAVEN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOMIMETICS; ELECTRON TRANSITIONS; ENZYMES; PROTON TRANSFER; REDOX REACTIONS;

ENZYME REGULATORY MECHANISMS; PROTON COUPLED ELECTRON TRANSFER; TYROSINES; ULTRAVIOLET PHOTOLYSIS;

PEPTIDES;

BIOMIMETIC MATERIAL; HISTIDINE; PEPTIDE; PHENOL; TYROSINE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL INTERACTION; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ENZYME MECHANISM; OXIDATION REDUCTION REACTION; PHOTOLYSIS; PKA; PROTON TRANSPORT; REGULATORY MECHANISM; THERMODYNAMICS;

AMINO ACID SEQUENCE; BIOMIMETIC MATERIALS; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRON TRANSPORT; ELECTRONS; ELECTROSTATICS; HYDROGEN-ION CONCENTRATION; MODELS, BIOLOGICAL; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES; PROTEIN STRUCTURE, TERTIARY; PROTONS; TYROSINE;

EID: 34247114694     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068805f     Document Type: Article

References (58)

1. Barry, B. A.; Einarsdottir, O. J. Phys. Chem. B 2005, 109, 6972-6981.
2. Britt, R. D. In Oxygenic Photosynthesis: The Light Reactions; Ort, D. R., Yocum, C. F., Eds.; Kluwer Academic Publisher: Dordrecht, 1996; Vol. 4, pp 137-164.
3. Pujols-Ayala, I.; Barry, B. A. Biochim. Biophys. Acta 2004, 1655, 205-216.
4. Malkowski, M. G. G., S. L.; Smith, W. L.; Garavito, R. M. Science 2000, 289, 1933-1937.
5. Stubbe, J.; van Der Donk, W. A. Chem. Rev. 1998, 98, 705-762.
6. Whittaker, M. M.; Whittaker, J. W. J. Biol. Chem. 1990, 265, 9610-9613.
7. Barry, B. A.; El-Deeb, M. K.; Sandusky, P. O.; Babcock, G. T. J. Biol. Chem. 1990, 265, 20139-20143.
8. Hulsebosch, R. J.; van der Brink, J. S.; Niewenhuis, S. A. M.; Gast, P.; Raap, J.; Lugtenburg, J.; Hoff, A. J. J. Am. Chem. Soc. 1997, 119, 8685-8694.
9. Vassiliev, I. R.; Offenbacher, A. R.; Barry, B. A. J. Phys. Chem. B 2005, 109, 23077-23085.
10. Dixon, W. T.; Murphy, D. J. Chem. Soc. Faraday Trans. 2 1976, 72, 1221-1229.
11. Rhile, I. J.; Markle, T. F.; Nagao, H.; DiPasquale, A. G.; Lam, O. P.; Lockwood, M. A.; Rotter, K.; Mayer, J. M. J. Am. Chem. Soc. 2006, 128, 6075-6088.
12. Chang, C. J.; Chang, M. C. Y.; Damrauer, N. H.; Nocera, D. G. Biochim. Biophys. Acta 2004, 1655, 13-28.
13. Marcus, R. A. Pure Appl. Chem. 1997, 69, 13-29.
14. Tommos, C. S., J.; Pilloud, D. L.; Wand, A. J.; Dutton, L. P. Biochemistry 1999, 38, 9495-9507.
15. Di Bilio, A. J.; Crane, B. R.; Wehbi, W. A.; Kiser, C. N.; Abu-Omar, M. M.; Carlos, R. M.; Richards, J. H.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 2001, 123, 3181-3182.
16. Shifman, J. M.; Moser, C. C.; Kaisbeck, W. A.; Bocian, D. F.; Dutton, P. L. Biochemistry 1998, 37, 16815-16827.
17. Jones, G., II; Vullev, V.; Braswell, E. H.; Zhu, D. J. Am. Chem. Soc. 2000, 122, 388-389.
18. Lombardi, A.; Nastri, F.; Pavone, V. Chem. Rev. 2001, 101, 3165-3190.
19. Gibney, B. R.; Huang, S. S.; Skalicky, J. J.; Fuentes, E. J.; Wand, A. J.; Dutton, P. L. Biochemistry 2001, 40, 10550-10561.
20. Kennedy, M. L.; Gibney, B. R. J. Am. Chem. Soc. 2002, 124, 6826-6827.
21. Discher, B. M.; Noy, D.; Strzalka, J.; Ye, S.; Moser, C. C.; Lear, J. D.; Blasie, J. K.; Dutton, P. L. Biochemistry 2005, 44, 12329-12343.
22. Cochran, F. V.; Wu, S. P.; Wang, W.; Nanda, V.; Saven, J. G.; Therien, M. J.; DeGrado, W. F. J. Am. Chem. Soc. 2005, 127, 1346-1347.
23. Shearer, J.; Long, L. M. Inorg. Chem. 2006, 45, 2358-2360.
24. Zhuang, J.; Amoroso, J. H.; Kinloch, R.; Dawson, J. H., Baldwin, M. J.; Gibney, B. R. Inorg. Chem. 2006, 45, 4685-4694.
25. Syud, F. A.; Stanger, H. E.; Gelman, S. H. J. Am. Chem. Soc. 2001, 123, 8667-8677.
26. Tatko, C.; Waters, M. L. Protein Sci. 2003, 12, 2443-2452.
27. Kumar, A.; Ernst, R. R.; Wuthrich, K. Biochem. Biophys. Res. Commun. 1980, 95, 1-6.
28. Piotto, M.; Saudek, V.; Sklenar, V. Biomol. NMR 1992, 2, 661-665.
29. Bax, A.; David, D. G. J. Magn. Reson. 1985, 65, 355-360.
30. Shaka, A. J.; Lee, C. J.; Pines, A. J. Magn. Reson. 1998, 77, 274-293.
31. Piantini, U.; Sorensen, O. W.; Ernst, R. R. J. Am. Chem. Soc. 1982, 124, 6800-6801.
32. Ranee, M.; Sorensen, O. W.; Bodenhausen, G.; Wagner, G.; Ernst, R. R.; Wuthrich, K. Biochem. Biophys. Res. Commun. 1983, 117, 479-485.
33. Delaglio, F.; Grzesiek, S.; Vuister, G. W.; Zhu, G.; Pheifer, J.; Bax, A. J. Biomol. NMR 1995, 6, 277-293.
34. Goddard, T. D.; Kneller, D. G. SPARKY 3; 1999.
35. Roberts, G. C. K. NMR of macromolecules a practical approach; Oxford University Press: New York, 1993.
36. Brunger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Acta Crystallogr., Sect. D 1998, 54, 905-921.
37. Schwieters, C. D.; Kuszewski, J. J.; Tjandra, N.; Core, G. M. J. Magn. Reson. 2003, 160, 65-73.
38. Nilges, M.; Gronenborn, A. M.; Brunger, A. T.; Clore, G. M. Protein Eng. 1988, 2, 27-38.
39. Laskowski, R. A.; MacArthur, M. W.; Thornton, J. M. Curr. Opin. Struct. Biol. 1998, 8, 631-639.
40. Clark, W. M. Oxidation reduction potentials of organic systems; The Williams and Wilkins Company: Baltimore, MD, 1960.
41. Moore, G. R.; Pettigrew, G. W. Cytochromes c. Evolutionary, Structural, and Physiochemical Aspects; Springer-Verlag: Berlin, 1990.
42. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
43. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
44. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
45. Frisch, et al. Gaussian03; Gaussian, Inc.: Wallingord, CT, 2004.
46. Range, K.; Ayala, I.; York, D.; Barry, B. A. J. Phys. Chem. 2006, 110, 10970-10981.
47. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265-3269.
48. Frisch, A.; Frisch, M.; Trucks, G. W. Gaussian03 User's Reference; Gaussian, Inc.: Wallinford, CT, 2003.
49. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49-56.
50. Laaksonen, L. gOpenMol 3.00 (htpp://222/cac.fi/gopenmol/); 2005.
51. Smith, C. K. W. J. M.; Regan, L. Biochemistry 1994, 33, 5510-5517.
52. Griffiths-Jones, S. R. M. A. J.; Searle, M. S. J. Mol. Biol. 1999, 292, 1051-1069.
53. Ciani, B. J. M.; Searle, M. J. Am. Chem. Soc. 2003, 125, 9038-9047.
54. Kiehna, S. E.; Waters, M. L. Protein Sci. 2003, 12, 2657-2667.
55. Waters, M. L. Curr. Opin. Chem. Biol. 2002, 6, 736-741.
56. Brabec, V.; Mornstein, V. Biophys. Chem. 1980, 12, 159-165.
57. Harriman, A. J. Phys. Chem. 1987, 91, 6102-6104.
58. Dean, J. A. Lange's Handbook of Chemistry; Mcgraw-Hill Inc.: New York, 1999.