Electron transfer mechanism in helical peptides

Journal of Physical Chemistry Letters

Volumn 3, Issue 6, 2012, Pages 709-713

  Mandal, Himadri Shekhar ^a   Kraatz, Heinz Bernhard ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMICAL STUDIES; ELECTRON TRANSFER; ELECTRON TRANSFER MECHANISMS; GOLD ELECTRODES; HELICAL CONFORMERS; HELICAL PEPTIDE; TUNNELING MECHANISM;

IRON COMPOUNDS; ORGANOMETALLICS; PEPTIDES; SELF ASSEMBLED MONOLAYERS;

ELECTRON TRANSITIONS;

EID: 84858692357     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz300008s     Document Type: Article

References (51)

1. Presta, L. G.; Rose, G. D. Helix Signals in Proteins Science 1988, 240, 1632-1641
2. Vullev, V. I.; Jones, J., II. Photoinduced Charge Transfer in Helical Polypeptides Res. Chem. Intermed. 2002, 28, 781-795
3. Yasutomi, S.; Morita, T.; Imanishi, Y.; Kimura, S. A Molecular Photodiode System That Can Switch Photocurrent Direction Science 2004, 304, 1944-1947 (Pubitemid 38822182)
4. Rau, H. K.; DeJonge, N.; Haehnel, W. Modular Synthesis of De Novo-Designed Metalloproteins for Light-Induced Electron Transfer Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 11526-11531 (Pubitemid 28460448)
5. Inai, Y.; Sisido, M.; Imanishi, Y. Photoinduced Electron Transfer on a Single α-Helical Polypeptide Chain: Evidence of a Through-Space Mechanism J. Phys. Chem. 1991, 95, 3847-3851
6. Batchelder, T. L.; Fox, R. J., III; Meier, M. S.; Fox, M. A. Intramolecular Excited State Electronic Coupling Along an α-Helical Peptide J. Org. Chem. 1996, 61, 4206-4209 (Pubitemid 126527928)
7. Morita, T.; Kimura, S. Long-Range Electron Transfer over 4 nm Governed by an Inelastic Hopping Mechanism in Self-Assembled Monolayers of Helical Peptides J. Am. Chem. Soc. 2003, 125, 8732-8733 (Pubitemid 36886204)
8. Page, C. C.; Moser, C. C.; Chen, X. P.; Dutton, L. Natural Engineering Principles of Electron Tunnelling in Biological Oxidation-Reduction Nature 1999, 402, 47-52
9. Zheng, Y.; Case, M. A.; Wishart, J. F.; McLendon, G. L. Do Main Chain Hydrogen Bonds Create Dominant Electron Transfer Pathways? An Investigation in Designed Proteins J. Phys. Chem. B. 2003, 107, 7288-7293
10. Beratan, D. N.; Betts, J. N.; Onuchic, J. N. Protein Electron Transfer Rates Set by The Bridging Secondary and Tertiary Structure Science 1991, 252, 1285-1288 (Pubitemid 21917037)
11. Sisido, M.; Hoshino, S.; Kusano, H.; Kuragaki, M.; Makino, M.; Sasaki, H.; Smith, T. A.; Ghiggino, K. P. Distance Dependence of Photoinduced Electron Transfer along α-Helical Polypeptides J. Phys. Chem. B. 2001, 105, 10407-10415 (Pubitemid 35338595)
12. Polo, F.; Antonello, S.; Formaggio, F.; Toniolo, C.; Maran, F. Evidence Against the Hopping Mechanism as an Important Electron Transfer Pathway for Conformationally Constrained Oligopeptides J. Am. Chem. Soc. 2004, 127, 492-493 (Pubitemid 40174353)
13. Antonello, S.; Formaggio, F.; Moretto, A.; Toniolo, C.; Maran, F. Anomalous Distance Dependence of Electron Transfer across Peptide Bridges J. Am. Chem. Soc. 2003, 125, 2874-2875 (Pubitemid 36512502)
14. Takeda, K.; Morita, T.; Kimura, S. Effects of Monolayer Structures on Long-Range Electron Transfer in Helical Peptide Monolayer J. Phys. Chem. B 2008, 112, 12840-12842
15. Kai, M.; Takeda, K.; Morita, T.; Kimura, S. Distance Dependence of Long-Range Electron Transfer through Helical Peptides J. Pept. Sci. 2008, 14, 192-202 (Pubitemid 351284915)
16. Arikuma, Y.; Nakayama, H.; Morita, T.; Kimura, S. Ultra-Long-Range Electron Transfer through a Self-Assembled Monolayer on Gold Composed of 120-Å-Long α-Helice Langmuir 2011, 27, 1530-1535
17. Watanabe, J.; Morita, T.; Kimura, S. Effects of Dipole Moment, Linkers, and Chromophores at Side Chains on Long-Range Electron Transfer through Helical Peptides J. Phys. Chem. B 2005, 109, 14416-14425 (Pubitemid 41156809)
18. Arikuma, Y.; Nakayama, H.; Morita, T.; Kimura, S. Electron Hopping over 100 Å along an α Helix Angew. Chem., Int. Ed. 2010, 49, 1800-1804
19. Mandal, H. S.; Kraatz, H.-B. Electron Transfer across α-Helical Peptides: Potential Influence of Molecular Dynamics Chem. Phys. 2006, 326, 246-251
20. Okamoto, S.; Morita, T.; Kimura, S. Electron Transfer through a Self-Assembled Monolayer of a Double-Helix Peptide with Linking the Terminals by Ferrocene Langmuir 2009, 25, 3297-3304
21. Lin, J.; Balabin, I. A.; Beratan, D. N. The Nature of Aqueous Tunneling Pathways between Electron-Transfer Proteins Science 2005, 310, 1311-1313 (Pubitemid 41698859)
22. van Amsterdam, I. M. C.; Ubbink, M.; Einsle, O.; Messerschmidt, A.; Merli, A.; Cavazzini, D.; Rossis, G. L.; Canters, G. W. Dramatic Modulation of Electron Transfer in Protein Complexes by Crosslinking Nature 2002, 9, 48-52 (Pubitemid 34049179)
23. Mandal, H. S.; Kraatz, H.-B. Effect of the Surface Curvature on the Secondary Structure of Peptides Adsorbed on Nanoparticles J. Am. Chem. Soc. 2007, 129, 6356-6357 (Pubitemid 46799316)
24. Sonoyama, M.; Mitaku, S. High-Temperature Intermediate State of Bacteriorhodopsin Prior to the Premelting Transition of Purple Membrane Revealed by Reactivity with Hydrolysis Reagent Hydroxylamine J. Phys. Chem. B 2004, 108, 19496-19500 (Pubitemid 40011201)
25. ET rates were estimated from Figure 3b of Sek, S.; Sepiol, A.; Tolak, A.; Misicka, A.; Bilewicz, R. Distance Dependence of the Electron Transfer Rate through Oligoglycine Spacers Introduced into Self-Assembled Monolayers J. Phys. Chem. B 2004, 108, 8102-8105
26. Finklea, H. O.; Hanshew, D. D. Electron-Transfer Kinetics in Organized Thiol Monolayers with Attached Pentaammine(pyridine)ruthenium Redox Centers J. Am. Chem. Soc. 1992, 114, 3173-3181
27. Simmons, J. G. Generalized Formula for the Electric Tunnel Effect between Similar Electrodes Separated by a Thin Insulating Film J. Appl. Phys. 1963, 34, 1793-1803
28. Kitagawa, K.; Morita, T.; Kimura, S. Molecular Rectification of a Helical Peptide with a Redox Group in the Metal-Molecule-Metal Junction J. Phys. Chem. B 2005, 109, 13906-13911 (Pubitemid 41163095)
29. Malak, R. A.; Gao, Z.; Wishart, J. F.; Isied, S. S. Long-Range Electron Transfer across Peptide Bridges: The Transition from Electron Superexchange to Hopping J. Am. Chem. Soc. 2004, 126, 13888-13889 (Pubitemid 39447041)
30. Giese, B.; Amaudrut, J.; Köhler, A.-K.; Spormann, M.; Wessely, S. Direct Observation of Hole Transfer through DNA by Hopping between Adenine Bases and by Tunneling Nature 2001, 412, 318-320 (Pubitemid 32691842)
31. Paul, A.; Watson, R. M.; Wierzbinski, E.; Davis, K. L.; Sha, A.; Achim, C.; Waldeck, D. H. Distance Dependence of the Charge Transfer Rate for Peptide Nucleic Acid Monolayers J. Phys. Chem. B 2010, 114, 14140
32. Petrov, E. G.; Ye., V.; Shevchenko, V.; Teslenko, V. I.; May, V. Nonadiabatic Donor-Acceptor Electron Transfer Mediated by a Molecular Bridge: A Unified Theoretical Description of the Superexchange and Hopping Mechanism J. Chem. Phys. 2001, 115, 7107-7122 (Pubitemid 33028841)
33. Bixon, M.; Jortner, J. Electron Transfer via Bridges J. Chem. Phys. 1997, 107, 5154-5170 (Pubitemid 127560686)
34. Cui, X. D.; Zarate, X.; Tomfohr, J.; Sankey, O. F.; Primak, A.; Moore, A. L.; Moore, T. A.; Gust, D.; Harris, G.; Lindsay, S. M. Making Electrical Contacts to Molecular Monolayers Namotechnology 2002, 13, 5-14 (Pubitemid 34180672)
35. Xu, D.; Watt, G. D.; Harb, J. N.; Davis, R. C. Electrical Conductivity of Ferritin Proteins by Conductive AFM Nano Lett. 2005, 5, 571-577 (Pubitemid 40609722)
36. Robinson, D. B.; Chidsey, C. E. D. Submicrosecond Electron Transfer to Monolayer-Bound Redox Species on Gold Electrodes at Large Overpotentials J. Phys. Chem. B 2002, 106, 10706-10713 (Pubitemid 35410267)
37. Sikes, H. D.; Smalley, J. F.; Dudek, S. P.; Cook, A. R.; Newton, M. D.; Chidsey, C. E. D.; Feldberg, S. W. Rapid Electron Tunneling through Oligophenylenevinylene Bridges Science 2001, 291, 1519-1523 (Pubitemid 32179213)
38. Scholtz, J. M.; Baldwin, R. L. The Mechanism of Alpha-Helix Formation by Peptides Annu. Rev. Biophys. Biomol. Struct. 1992, 21, 95-118
39. Harrison, R. S.; Shepherd, N. E.; Hoang, H. N.; Ruiz-Gómez, G.; Hill, T. A.; Driver, R. W.; Desai, V. S.; Young, P. R.; Abbenante, G.; Fairliea, D. P. Downsizing Human, Bacterial, and Viral Proteins to Short Water-Stable Alpha Helices that Maintain Biological Potency Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 11686-11691
40. Su, J. Y.; Hodges, R. S.; Kay, C. M. Effect of Chain Length on the Formation and Stability of Synthetic α-Helical Coiled Coils Biochemistry 1994, 33, 15501-15510
41. Beratan, D. N.; Onuchic, J. N.; Winkler, J. R.; Gray, H. B. Electron-Tunneling Pathways in Proteins Science 1992, 258, 1740-1741 (Pubitemid 23087338)
42. de Rege, P. J. F.; Williams, S. A. Direct Evaluation of Electronic Coupling Mediated by Hydrogen Bonds: Implications for Biological Electron Transfer Science 1995, 269, 1409-1413
43. 0 = -0.1 eV for ET from tryptophan to pyrene across a series of helical peptides. Jones, G.; Zhou, X.; Vullev, V. I. Photoinduced Electron Transfer in α-Helical Polypeptides: Dependence on Conformation and Electron Donor-Acceptor Distance Photochem. Photobiol. Sci. 2003, 2, 1080-1087 (Pubitemid 41662935)
44. Langen, R.; Chang, I.-J.; Germanas, J. P.; Richards, J. H.; Winkler, J. R.; Gray, H. B. Electron Tunneling in Proteins: Coupling through a Beta Strand Science 1995, 268, 1733-1735
45. 10-Helix in a Fluorescence-Labeled Peptide Angew. Chem., Int. Ed. 1996, 35, 326-329
46. 10-Helix Transitions in α-Methylalanine Homopeptides: Conformational Transition Pathway and Potential of Mean Force Biopolymers 1994, 34, 75-90
47. Kitagawa, K.; Morita, T.; Kimura, S. A Helical Molecule That Exhibits Two Lengths in Response to an Applied Potential Angew. Chem., Int. Ed. 2005, 44, 6330-6333 (Pubitemid 41454655)
48. Balabin, I. A.; Beratan, D. N.; Skourtis, S. S. Persistence of Structure Over Fluctuations in Biological Electron-Transfer Reactions Phys. Rev. Lett. 2008, 101, 158102-158105
49. Kraatz, H.-B.; Bediako-Amoa, I.; Gyepi-Garbrah, S. H.; Sutherland, T. C. Electron Transfer through H-bonded Peptide Assemblies J. Phys. Chem. B 2004, 108, 20164-20172 (Pubitemid 40079157)
50. Irene, B.-A.; Sutherland, T. C.; Li, C.-Z.; Silerova, R.; Kraatz, H.-B. Electrochemical and Surface Study of Ferrocenoyl Oligopeptides J. Phys. Chem. B 2004, 108, 704-714
51. Dey, S. K.; Long, Y. T.; Chowdhury, S.; Sutherland, T. C.; Mandal, H. S.; Kraatz, H.-B. Study of Electron Transfer in Ferrocene-Labeled Collagen-like Peptides Langmuir 2007, 23 (12) 6475-6477 (Pubitemid 46943465)