Self-assembling monolayers of helical oligopeptides on gold with applications in molecular electronics

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Andrew E. Strong and Barry D. Moore


Abstract

A generic strategy is outlined for preparing a chiral functionalised surface using self-assembled monolayers (SAMs) of helical oligopeptides for intended application in molecular electronics, sensors and catalysis. Helical peptides have been designed and synthesised with 3 Met or 2 Cys residues per peptide, placed in the sequence so that in a helical conformation their side-chains are on the same side of the helix and organised to bind to gold by self-assembly of the thioether or thiol functions. Circular dichroism (CD) of the Met-containing peptides showed that they are mainly helical in organic solvents and FT-RAIRS (reflection-absorption infrared spectroscopy) of their SAMs on gold confirmed that they are aligned with the helix axes parallel to the surface. However complete coverage of the surface is dependent critically on the preparation of the gold. CD of an oligopeptide containing 2 Cys residues suggested that the conformation was a mixture of helix and random coil. Films of this peptide adsorbed from different solvents were characterised by ellipsometry and cyclic voltammetry. Ethanol and methanol led to multilayer formation indicating protic solvents destabilise the helical structure, allowing formation of intermolecular disulfide bonds. By contrast the aprotic solvent acetonitrile led to formation of a close-packed self-assembled monolayer suitable for elaboration into a functionalised supramolecular architecture.


References

  1. C. A. Mirkin and M. A. Ratner, Annu. Rev. Phys. Chem., 1992, 43, 719 CrossRef.
  2. R. W. Munn, Biosystems, 1992, 27, 207 CAS.
  3. F. L. Carter, Molecular Electronic Devices II, Marcel Dekker, New York, 1987 Search PubMed.
  4. A. Aviram and M. A. Ratner, Chem. Phys. Lett., 1974, 29, 277 CrossRef CAS.
  5. J. J. Hopfield, J. N. Onuchic and D. N. Beratan, J. Phys. Chem., 1989, 93, 6350 CrossRef CAS.
  6. H. Tachibani, T. Nakamura, M. Matsumoto, H. Komizu, E. Manda, H. Niino, A. Yabe and Y. Kawabata, J. Am. Chem. Soc., 1989, 111, 3080 CrossRef CAS.
  7. C. Joachim and J. P. Launay, J. Mol. Electronics, 1990, 6, 37 Search PubMed.
  8. M. D. Ward, Chem. Soc. Rev., 1995, 24, 121 RSC.
  9. M. Mutter and R. Hersperberger, Angew. Chem., Int. Ed. Engl., 1990, 29, 185 CrossRef.
  10. G. Hungerford, M. Martinez-Insua, D. J. S. Birch and B. D. Moore, Angew. Chem., Int. Ed. Engl., 1996, 35, 326 CrossRef CAS.
  11. R. A. Bissell, E. Cordova, A. E. Kaifer and J. F. Stoddart, Nature, 1994, 369, 133 CrossRef.
  12. L. Zelikovich, J. Libman and A. Shanzer, Nature, 1995, 374, 790 CrossRef CAS.
  13. M. P. Debreczeny, W. A. Svec, E. M. Marsh and R. Wasielewski, J. Am. Chem. Soc., 1996, 118, 8174 CrossRef CAS.
  14. R. R. Birge, Sci. Am., 1995, March, p. 66 Search PubMed.
  15. U. P. Wild, S. Bernet, B. Kohler and A. Renn, Pure Appl. Chem., 1992, 64, 1335 CAS.
  16. C. D. Bain and G. M. Whitesides, Angew. Chem., Int. Ed. Engl., 1989, 28, 506 CrossRef.
  17. N. L. Abbott and G. M. Whitesides, Langmuir, 1994, 10, 1493 CrossRef CAS.
  18. K. L. Prime and G. M. Whitesides, Science, 1991, 252, 1164 CrossRef CAS.
  19. G. M. Whitesides and P. E. Laibinis, Langmuir, 1990, 6, 87 CrossRef CAS.
  20. L.-H. Guo, J. S. Facci and G. McLendon, J. Phys. Chem., 1995, 99, 8458 CrossRef CAS.
  21. L. A. Hockett and S. E. Creager, Langmuir, 1995, 11, 2318 CrossRef CAS.
  22. J. N. Richardson, G. K. Rowe, M. T. Carter, L. M. Tender, L. S. Curtin, S. R. Peck and R. W. Murray, Electrochim. Acta, 1995, 40, 1331 CrossRef CAS.
  23. L. H. Dubois and R. G. Nuzzo, Annu. Rev. Phys. Chem., 1992, 43, 437 CrossRef CAS.
  24. A. Ulman, Ultrathin Organic Films; From Langmuir-Blodgett to Self-Assembly, Academic Press, Boston, 1991 Search PubMed.
  25. W. B. Caldwell, K. Chen, B. R. Herr, C. A. Mirkin, J. C. Hulteen and R. P. Van Duyne, Langmuir, 1994, 10, 4109 CrossRef CAS.
  26. C. M. Yip and M. D. Ward, Langmuir, 1994, 10, 549 CrossRef CAS.
  27. X. Tang, T. Schneider and D. A. Buttry, Langmuir, 1994, 10, 2235 CrossRef CAS.
  28. L. Haussling, H. Ringsdorf, F.-J. Schmitt and W. Knoll, Langmuir, 1991, 7, 1837 CrossRef.
  29. W. S. V. Kwan, L. Atanasoska and L. L. Miller, Langmuir, 1991, 7, 1419 CrossRef.
  30. J. M. Tour, L. Jones II, D. L. Pearson, J. J. S. Lamba, T. P. Burgin, G. M. Whitesides, D. L. Allara, A. N. Parikh and S. V. Atre, J. Am. Chem. Soc., 1995, 117, 9529 CrossRef CAS.
  31. E. U. Thoden van Velzen, J. F. J. Engbersen, P. J. de Lange, J. W. G. Mahy and D. N. Reinhoudt, J. Am. Chem. Soc., 1995, 117, 6853 CrossRef CAS.
  32. H. Adams, F. Davis and C. J. M. Stirling, J. Chem. Soc., Chem. Commun., 1994, 2527 RSC.
  33. R. P. H. Kooyman, D. J. van den Heuvel, J. W. Drijfhout and G. W. Welling, Thin Solid Films, 1994, 244, 913 CrossRef CAS.
  34. C. Duschl, M. Liley, G. Corradin and H. Vogel, Biophys. J., 1994, 67, 1229 CrossRef CAS.
  35. C. D. Bain, J. Evall and G. M. Whitesides, J. Am. Chem. Soc., 1989, 111, 7155 CrossRef CAS.
  36. M. Knichel, P. Heiduschka, W. Beck, G. Jung and W. Gopel, Sens. Actuators B, 1995, 28, 85 CrossRef.
  37. C. Duschl, A. F. Sevinlandais and H. Vogel, Biophys. J., 1996, 70, 1985 CAS.
  38. M. Boncheva and H. Vogel, Biophys. J., 1997, 73, 1056 CrossRef CAS.
  39. J. K. Whitesell and H. K. Chang, Science, 1993, 261, 73 CrossRef CAS.
  40. S. Sakamoto, H. Aoyagi, N. Nakashima and H. Mihara, J. Chem. Soc., Perkin Trans. 2, 1996, 2319 RSC.
  41. R. Naumann, A. Jonczyk, R. Kopp, J. van Esch, H. Ringsdorf, W. Knoll and P. Graber, Angew. Chem., Int. Ed. Engl., 1995, 34, 2056 CrossRef CAS.
  42. L. Scheibler, P. Dumy, D. Stamou, C. Duschl, H. Vogel and M. Mutter, Tetrahedron, 1998, 54, 3725 CrossRef CAS.
  43. A. E. Strong and B. D. Moore, Chem. Commun., 1998, 473 RSC.
  44. I. L. Karle and P. Balaram, Biochemistry, 1990, 29, 6747 CrossRef CAS.
  45. C. Toniolo and E. Benedetti, Trends Biochem. Sci., 1991, 16, 350 CrossRef CAS.
  46. F. Donald, G. Hungerford, D. J. S. Birch and B. D. Moore, J. Chem. Soc., Chem. Commun., 1995, 313 RSC.
  47. G. P. Dado and S. H. Gellman, J. Am. Chem. Soc., 1993, 115, 12609 CrossRef CAS.
  48. S. Marqusee, V. H. Robbins and R. L. Baldwin, Proc. Natl. Acad. Sci. USA, 1989, 86, 5286 CAS.
  49. S. P. Ho and W. F. DeGrado, J. Am. Chem. Soc., 1987, 109, 6751 CrossRef CAS.
  50. R. W. Woody, in The Peptides: Analysis, synthesis, biology, 1985, Vol. 7, p. 15 Search PubMed.
  51. P. I. Haris and D. Chapman, Biopolymers, 1995, 37, 251 CrossRef CAS.
  52. R. J. Greenler, J. Chem. Phys., 1966, 44, 310 CrossRef CAS.
  53. S. Krimm and J. Bandekar, Adv. Protein Chem., 1986, 38, 181 CAS.
  54. M. D. Porter, T. B. Bright, D. L. Allara and C. E. D. Chidsey, J. Am. Chem. Soc., 1987, 109, 3559 CrossRef CAS.
  55. E. B. Troughton, C. D. Bain, G. M. Whitesides, R. G. Nuzzo, D. L. Allara and M. D. Porter, Langmuir, 1988, 4, 365 CrossRef CAS.
  56. A. E. Strong, Ph. D. Thesis, University of Strathclyde, 1997 Search PubMed.
  57. G. B. Fields and R. L. Noble, Int. J. Pept. Protein Res., 1990, 35, 161 CAS.
  58. D. A. Pearson, M. Blanchette, M. L. Baker and C. A. Guindon, Tetrahedron Lett., 1989, 30, 2739 CrossRef.
  59. F. Albericio, R. P. Hammer, C. García-Echeverría, M. A. Molins, J. L. Chang, M. Pons, E. Giralt and G. Barany, Int. J. Pept. Protein Res., 1991, 37, 402 CAS.
  60. S. M. Miick, K. Casteel and G. L. Millhauser, Biochemistry, 1993, 32, 8014 CrossRef CAS.
  61. T. Iwata, S. Lee, O. Oishi, H. Aoyagi, M. Ohno, K. Anzai, Y. Kirino and G. Sugihara, J. Biol. Chem., 1994, 269, 4928 CAS.
  62. W. L. Fiori, S. M. Miick and G. L. Millhauser, Biochemistry, 1993, 32, 11957 CrossRef CAS.
  63. C. G. Pierpont, H. H. Downs and T. G. Rukavina, J. Am. Chem. Soc., 1974, 96, 5573 CrossRef CAS.
  64. J. F. Rodriguez, T. Mebrahtu and M. P. Soriaga, J. Electroanal. Chem., 1987, 233, 283 CrossRef CAS.
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