Distance dependence of long-range electron transfer through helical peptides

Journal of Peptide Science

Volumn 14, Issue 2, 2008, Pages 192-202

  Kai, Minako ^a   Takeda, Kazuki ^a   Morita, Tomoyuki ^a   Kimura, Shunsaku ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Disulfide; Electrochemistry; Electron transfer; Ferrocene; Gold; Helical peptide; Hopping mechanism; Self assembled monolayer

Indexed keywords

DISULFIDE; FERROCENE; GOLD; PEPTIDE DERIVATIVE; SULFUR;

AMINO TERMINAL SEQUENCE; AMPEROMETRY; ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY; ELECTRON TRANSPORT; ELLIPSOMETRY; HYDROGEN BOND; MOLECULAR DYNAMICS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; REFLECTOMETRY;

CIRCULAR DICHROISM; ELECTRONS; MOLECULAR STRUCTURE; PEPTIDES;

EID: 39649105446     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.974     Document Type: Article

References (45)

1. Mayo SL, Ellis WR, Crutchley RJ, Gray HB. Long-range electron-transfer in heme-proteins. Science 1986; 233: 948-952.
2. Beratan DN, Onuchic JN, Winkler JR, Gray HB. Electron-tunneling pathways in proteins. Science 1992; 258: 1740-1741.
3. Langen R, Chang IJ, Germanas JP, Richards JH, Winkler JR, Gray HB. Electron-tunneling in proteins-coupling through a beta-strand. Science 1995; 268: 1733-1735.
4. Isied SS. Long-range electron-transfer in peptides and proteins. Prog. Inorg. Chem. 1984; 32: 443-517.
5. Shin YGK, Newton MD, Isied SS. Distance dependence of electron transfer across peptides with different secondary structures: The role of peptide energetics and electronic coupling. J. Am. Chem. Soc. 2003; 125: 3722-3732.
6. Hol WGJ. The role of the alpha-helix dipole in protein function and structure. Prog. Biophys. Mol. Biol. 1985; 45: 149-195.
7. Vassilian A, Wishart JF, Vanhemelryck B, Schwarz H, Isied SS. Electron-transfer across polypeptides.6. Long-range electron-transfer in osmium-ruthenium binuclear complexes bridged with oligoproline peptides. J. Am. Chem. Soc. 1990; 112: 7278-7286.
8. Ogawa MY, Wishart JF, Young ZY, Miller JR, Isied SS. Distance dependence of intramolecular electron-transfer across oligoprolines in [(bpy)2ruiil-(pro)n-coiii {nh3) 5] 3+, n = 1-6- different effects for helical and nonhelical polyproline-ii structures. J. Phys. Chem. 1993; 97: 11456-11463.
9. Sisido M, Hoshino S, Kusano H, Kuragaki M, Makino M, Sasaki H, Smith TA, Ghiggino KP. Distance dependence of photoinduced electron transfer along alpha-helical polypeptides. J. Phys. Chem. B 2001; 105: 10407-10415.
10. Morita T, Kimura S. Long-range electron transfer over 4nm governed by an inelastic hopping mechanism in self-assembled monolayers of helical peptides. J. Am. Chem. Soc. 2003; 125: 8732-8733.
11. 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.
12. Galka MM, Kraatz HB. Electron transfer studies on self-assembled monolayers of helical ferrocenoyl-oligoproline-cystamine bound to gold. Chemphyschem 2002; 3: 356-359.
13. Kraatz HB, Bediako-Amoa I, Gyepi-Garbrah SH, Sutherland TC. Electron transfer through h-bonded peptide assemblies. J. Phys. Chem. B 2004; 108: 20164-20172.
14. Mandal HS, Kraatz HB. Electron transfer across alpha-helical peptides: potential influence of molecular dynamics. Chem. Phys. 2006; 326: 246-251.
15. Sek S, Tolak A, Misicka A, Palys B, Bilewicz R. Asymmetry of electron transmission through monolayers of helical polyalanine adsorbed on gold surfaces. J. Phys. Chem. B 2005; 109: 18433-18438.
16. Xiao XY, Xu BQ, Tao NJ. Conductance titration of single-peptide molecules. J. Am. Chem. Soc. 2004; 128: 5370-5371.
17. Sek S, Swiatek K, Misicka A. Electrical behavior of molecular junctions incorporating alpha-helical peptide. J. Phys. Chem. B 2005; 109: 23121-23124.
18. Sek S, Misicka A, Swiatek K, Maicka E. Conductance of alpha-helical peptides trapped within molecular junctions. J. Phys. Chem. B 2006; 110: 19671-19677.
19. Long YT, Abu-Rhayem E, Kraatz HB. Peptide electron transfer: more questions than answers. Chem. A Eur. J. 2005; 11: 5186-5194.
20. Adams DM, Brus L, Chidsey CED, Creager S, Creutz C, Kagan CR, Kamat PV, Lieberman M, Lindsay S, Marcus RA, Metzger RM, Michel-Beyerle ME, Miller JR, Newton MD, Rolison DR, Sankey O, Schanze KS, Yardley J, Zhu XY. Charge transfer on the nanoscale: current status. J. Phys. Chem. B 2003; 107: 6668-6697.
21. 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.
22. 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. 2005; 127: 492-493.
23. Malak RA, Gao ZN, Wishart JF, Isied SS. Long-range electron transfer across peptide bridges: The transition from electron superexchange to hopping. J. Am. Chem. Soc. 2004; 128: 13888-13889.
24. Otoda K, Kitagawa Y, Kimura S, Imanishi Y. Chain-length dependent transition of 3{10)- to alpha-helix of boc-(ala-aib) (n)-ome. Biopolymers 1993; 33: 1337-1345.
25. Chen YH, Yang JT, Martinez HM. Determination of secondary structures of proteins by circular-dichroism and optical rotatory dispersion. Biochemistry 1972; 11: 4120-4131.
26. Gremlich HU, Fringeli UP, Schwyzer R. Conformational-changes of adrenocorticotropin peptides upon interaction with lipid-membranes revealed by infrared attenuated total reflection spectroscopy. Biochemistry 1983; 22: 4257-4264.
27. Miura Y, Kimura S, Imanishi Y, Umemura J. Formation of oriented helical peptide layers on a gold surface due to the self-assembling properties of peptides. Langmuir 1998; 14: 6935-6940.
28. Tsuboi M. Infrared dichroism and molecular conformation of alpha-form poly-gamma-benzyl-l-glutamate. J. Polym. Sci. 1962; 59: 139-153.
29. Kennedy DF, Crisma M, Toniolo C, Chapman D. Studies of peptides forming 3(10)-helices and alpha-helices and beta-bend ribbon structures in organic solution and in model biomembranes by fourier-transform infrared-spectroscopy. Biochemistry 1991; 30: 6541-6548.
30. Steinem C, Janshoff A, Ulrich WP, Sieber M, Galla HJ. Impedance analysis of supported lipid bilayer membranes: A scrutiny of different preparation techniques. Biochim. Biophys. Acta 1996; 1279: 169-180.
31. Wu XZ, Zhang WZ, Hou Y. Assessing nonlinearity in impedance models-the model characteristics of an equivalent-circuit with a cpe. J. Electroanal. Chem. 1995; 398: 1-4.
32. Protsailo LV, Fawcett WR. Studies of electron transfer through self-assembled monolayers using impedance spectroscopy. Electrochim. Acta 2000; 45: 3497-3505.
33. Yamada T, Nango M, Ohtsuka T. Potential modulation reflectance of manganese halogenated tetraphenylporphyrin derivatives assemble on gold electrodes. J. Electroanal. Chem. 2002; 528: 93-102.
34. Creager SE, Wooster TT. A new way of using ac voltammetry to study redox kinetics in electroactive monolayers. Anal. Chem. 1998; 70: 4257-4263.
35. Benedetti E, Di Blasio B, Pavone V, Pedone C, Santini A, Crisma M, Toniolo C. In Molecular Conformation and Biological Interactions, Balaram P, Ramaseshan S (eds). Indian Academy of Science: Bangalore, 1991; 497-502.
36. Toniolo C, Polese A, Formaggio F, Crisma M, Kamphuis J. Circular dichroism spectrum of a peptide 3(10)-helix. J. Am. Chem. Soc. 1996; 118: 2744-2745.
37. Niwa M, Morikawa M, Higashi N. Controllable orientation of helical poly(1-glutamic acid) rods through macrodipole interaction on gold surfaces and vectorial electron transfer. Angew. Chem. Int. Ed. Engl. 2000; 39: 960-963.
38. Finklea HO, Ravenscroft MS, Snider DA. Electrolyte and temperature effects on long-range electron-transfer across self-assembled monolayers. Langmuir 1993; 9: 223-227.
39. Finklea HO, Hanshew DD. Electron-transfer kinetics in organized thiol monolayers with attached pentaammine(pyridine)ruthenium redox centers. J. Am. Chem. Soc. 1992; 114: 3173-3181.
40. Sek S, Palys B, Bilewicz R. Contribution of intermolecular interactions to electron transfer through monolayers of alkanethiols containing amide groups. J. Phys. Chem. B2002; 106:5907-5914.
41. Weinkauf R, Schanen P, Metsala A, Schlag EW, Burgle M, Kessler H. Highly efficient charge transfer in peptide cations in the gas phase: Threshold effects and mechanism. J. Phys. Chem. 1996; 100: 18567-18585.
42. Miller LL, Mayeda EA, Nordblom GD. Simple, comprehensive correlation of organic oxidation and ionization potentials. J. Org. Chem. 1972; 37: 916-&.
43. Tomfohr JK, Sankey OF. Complex band structure, decay lengths, and fermi level alignment in simple molecular electronic systems. Phys. Rev., B 2002; 65: 245105-1-12.
44. Beerbom MM, Gargagliano R, Schlaf R. Determination of the electronic structure of self-assembled 1-cysteine/au interfaces using photoemission spectroscopy. Langmuir 2005; 21: 3551-3558.
45. Petrov EG, May V, Hanggi P. Controlling electron transfer processes through short molecular wires. Chem. Phys. 2002; 281: 211-224.