Modulating the pH-dependent redox potential of a flavin analog via incorporation into a self-assembled monolayer on gold

Chemical Communications

Volumn , Issue 1, 1999, Pages 65-66

  Tam Chang, Suk Wah ^a   Mason, James ^a   Iverson, Isaac ^a   Hwang, Ki Oh ^a   Leonard, Christa ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GOLD; NITROGEN; PROTON; QUERCETIN;

ARTICLE; ELECTROCHEMISTRY; OXIDATION REDUCTION POTENTIAL; PH;

EID: 0033531129     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806315j     Document Type: Article

References (28)

1. C. Walsh, Enzymatic Reaction Mechanisms, W. H. Freeman and Company, New York, 1979; P. Hemmerich, C. Veeger and H. C. S. Wood, Angew. Chem., Int. Ed. Engl., 1965, 4, 671.
2. C. Walsh, Enzymatic Reaction Mechanisms, W. H. Freeman and Company, New York, 1979; P. Hemmerich, C. Veeger and H. C. S. Wood, Angew. Chem., Int. Ed. Engl., 1965, 4, 671.
3. Elegant models have been designed to quantify the effects of π-stacking on flavin redox chemistry in aprotic solvents: A. Niemz, J. Imbriglio and V. M. Rotello, J. Am. Chem. Soc., 1997, 119, 887; E. C. Breinlinger, A. Niemz and V. M. Rotello, J. Am. Chem. Soc., 1995, 117, 5379; E. C. Breinlinger and V. M. Rotello, J. Am. Chem. Soc., 1997, 119, 1165.
4. Elegant models have been designed to quantify the effects of π-stacking on flavin redox chemistry in aprotic solvents: A. Niemz, J. Imbriglio and V. M. Rotello, J. Am. Chem. Soc., 1997, 119, 887; E. C. Breinlinger, A. Niemz and V. M. Rotello, J. Am. Chem. Soc., 1995, 117, 5379; E. C. Breinlinger and V. M. Rotello, J. Am. Chem. Soc., 1997, 119, 1165.
5. Elegant models have been designed to quantify the effects of π-stacking on flavin redox chemistry in aprotic solvents: A. Niemz, J. Imbriglio and V. M. Rotello, J. Am. Chem. Soc., 1997, 119, 887; E. C. Breinlinger, A. Niemz and V. M. Rotello, J. Am. Chem. Soc., 1995, 117, 5379; E. C. Breinlinger and V. M. Rotello, J. Am. Chem. Soc., 1997, 119, 1165.
6. B. J. Stockman, T. E. Richardson and R. P. Swenson, Biochemistry, 1994, 33, 15 298; R. P. Swenson and G. D. Krey, Biochemistry, 1994, 33, 8505; F. C. Chang and R. P. Swenson, Biochemistry, 1997, 36, 9013; M. Inoue, Y. Okudo, I. Ishida and M. Nakagaki, Arch. Biochem. Biophys., 1983, 227, 52.
7. B. J. Stockman, T. E. Richardson and R. P. Swenson, Biochemistry, 1994, 33, 15 298; R. P. Swenson and G. D. Krey, Biochemistry, 1994, 33, 8505; F. C. Chang and R. P. Swenson, Biochemistry, 1997, 36, 9013; M. Inoue, Y. Okudo, I. Ishida and M. Nakagaki, Arch. Biochem. Biophys., 1983, 227, 52.
8. B. J. Stockman, T. E. Richardson and R. P. Swenson, Biochemistry, 1994, 33, 15 298; R. P. Swenson and G. D. Krey, Biochemistry, 1994, 33, 8505; F. C. Chang and R. P. Swenson, Biochemistry, 1997, 36, 9013; M. Inoue, Y. Okudo, I. Ishida and M. Nakagaki, Arch. Biochem. Biophys., 1983, 227, 52.
9. B. J. Stockman, T. E. Richardson and R. P. Swenson, Biochemistry, 1994, 33, 15 298; R. P. Swenson and G. D. Krey, Biochemistry, 1994, 33, 8505; F. C. Chang and R. P. Swenson, Biochemistry, 1997, 36, 9013; M. Inoue, Y. Okudo, I. Ishida and M. Nakagaki, Arch. Biochem. Biophys., 1983, 227, 52.
10. S. Fukuzumi, K. Tanii and T. Tanaka, Chem. Commun., 1989, 816; S. W. Tam, L. Jimenez and F. Diederich, J. Am. Chem. Soc., 1992, 114, 1503; M. Ishikawa, H. Okimoto, M. Masayuki and Y. Matsuda, Chem. Lett., 1996, 953.
11. S. Fukuzumi, K. Tanii and T. Tanaka, Chem. Commun., 1989, 816; S. W. Tam, L. Jimenez and F. Diederich, J. Am. Chem. Soc., 1992, 114, 1503; M. Ishikawa, H. Okimoto, M. Masayuki and Y. Matsuda, Chem. Lett., 1996, 953.
12. S. Fukuzumi, K. Tanii and T. Tanaka, Chem. Commun., 1989, 816; S. W. Tam, L. Jimenez and F. Diederich, J. Am. Chem. Soc., 1992, 114, 1503; M. Ishikawa, H. Okimoto, M. Masayuki and Y. Matsuda, Chem. Lett., 1996, 953.
13. C. E. D. Chidsey, C. R. Bertozzi, T. M. Putvinski and A. M. Mujsce, J. Am. Chem. Soc., 1990, 112, 4301; N. L. Abbott and G. M. Whitesides, Langmuir, 1994, 10, 1493; D. M. Collard and M. A. Fox, Langmuir, 1991, 71, 1192.
14. C. E. D. Chidsey, C. R. Bertozzi, T. M. Putvinski and A. M. Mujsce, J. Am. Chem. Soc., 1990, 112, 4301; N. L. Abbott and G. M. Whitesides, Langmuir, 1994, 10, 1493; D. M. Collard and M. A. Fox, Langmuir, 1991, 71, 1192.
15. C. E. D. Chidsey, C. R. Bertozzi, T. M. Putvinski and A. M. Mujsce, J. Am. Chem. Soc., 1990, 112, 4301; N. L. Abbott and G. M. Whitesides, Langmuir, 1994, 10, 1493; D. M. Collard and M. A. Fox, Langmuir, 1991, 71, 1192.
16. H. C. D. Long and D. A. Buttry, Langmuir, 1992, 8, 2491; S. E. Creager and G. K. Rowe, Anal. Chim. Acta, 1991, 246, 233; H. O. Finklea and D. D. Hanshew, J. Am. Chem. Soc., 1992, 114, 3173.
17. H. C. D. Long and D. A. Buttry, Langmuir, 1992, 8, 2491; S. E. Creager and G. K. Rowe, Anal. Chim. Acta, 1991, 246, 233; H. O. Finklea and D. D. Hanshew, J. Am. Chem. Soc., 1992, 114, 3173.
18. H. C. D. Long and D. A. Buttry, Langmuir, 1992, 8, 2491; S. E. Creager and G. K. Rowe, Anal. Chim. Acta, 1991, 246, 233; H. O. Finklea and D. D. Hanshew, J. Am. Chem. Soc., 1992, 114, 3173.
19. For flavin analogs immobilized on gold via other linkers, see: S. Sakamoto, H. Aoyagi, N. Nakashima and H. Mihara, J. Chem. Soc., Perkin Trans. 2, 1996, 2319; B. Mallik and D. Gani, J. Electroanal. Chem., 1992, 326, 37.
20. For flavin analogs immobilized on gold via other linkers, see: S. Sakamoto, H. Aoyagi, N. Nakashima and H. Mihara, J. Chem. Soc., Perkin Trans. 2, 1996, 2319; B. Mallik and D. Gani, J. Electroanal. Chem., 1992, 326, 37.
21. Disulfide is used instead of the analogous thiol due to the thiol's vulnerability to oxidation by the flavin moiety.
22. B. Janik and P. J. Elving, Chem. Rev., 1968, 68, 295.
23. 0-pH curve is 0.059 p/n at 25 °C (where p and n are the numbers of protons and electrons involved respectively) P. J. Elving, Pure Appl. Chem., 1963, 7, 423.
24. 0-pH plots, see: W. M. Clark, Oxidation-Reduction Potentials of Organic Systems, Williams and Wilkin Co., Baltimore, 1960, pp. 118.
25. W. M. Clark, Oxidation-Reduction Potentials of Organic Systems, Williams and Wilkin Co., Baltimore, 1960, p. 439.
26. C. D. Bain, G. M. Whitesides, Langmuir, 1989, 5, 1370; T. R. Lee, R. I. Carey, H. A. Biebuyck and G. M. Whitesides, Langmuir, 1994, 10, 741.
27. C. D. Bain, G. M. Whitesides, Langmuir, 1989, 5, 1370; T. R. Lee, R. I. Carey, H. A. Biebuyck and G. M. Whitesides, Langmuir, 1994, 10, 741.
28. In addition to the decrease in peak areas, the full-widths at half maxima and the separation between the anodic and cathodic peaks (ca. 70 mV) in the mixed SAMs are smaller than those of the SAM from I.