Linear free energy substitutent effect on flavin redox chemistry

Journal of the American Chemical Society

Volumn 120, Issue 10, 1998, Pages 2251-2255

  Hasford, Justin J ^a   Rizzo, Carmelo J ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

QUERCETIN; RIBOFLAVIN DERIVATIVE;

ARTICLE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; ENERGY TRANSFER; ENZYME ACTIVE SITE; NONHUMAN; OXIDATION REDUCTION POTENTIAL; STRUCTURE ACTIVITY RELATION;

EID: 0032542722     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972992n     Document Type: Article

References (45)

1. (a) Muller, F. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton, FL, 1991; Vol. 1, pp 1-71.
2. (b) Stankovich, M. T. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton, FL, 1991; Vol. 1, pp 401-425
3. (a) Edmondson, D. E.; De Francesco, R. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton, FL, 1991; Vol. 1, pp 73-103.
4. (b) Matsui, K.; Kasai, S. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton, FL, 1991; Vol. 1, pp 105-120.
5. (c) Decker, K. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton, FL, 1991; Vol. 2, pp 343-375.
6. (d) Decker, K. F. Annu. Rev. Nutr. 1993, 13, 17.
7. (e) Decker, K.; Brandsch, R. Methods Enzymol. 1997, 280, 413.
8. (a) Kita, A.; Kasai, S.; Miki, K. J. Biochem. 1995, 117, 575.
9. (b) Moore, S. A.; James, M. N. G.; O'Kane, D. J. O.; Lee, J. EMBO J. 1993, 12, 1767.
10. (a) Barber, M. J.; Neame, P. J.; Lim, L. W.; White, S.; Mathews, F. S. J. Biol. Chem. 1992, 267, 6611.
11. (b) Lim, L. W.; Shamala, N.; Mathews, F. S.; Steenkamp, D. J.; Hamlin, R.; Xuong, N. J. Mol. Biol. 1986, 261, 15140.
12. (c) Steenkamp, D. J.; Mathews, F. S. In Chemistry and Biochemistry of Flavoenzymes; Muller, F., Ed.; CRC Press: Boca Raton, FL. 1991; Vol. 2, pp 395-424.
13. (a) Breinlinger, E.; Niemz, A.; Rotello, V. M. J. Am. Chem. Soc. 1995, 117, 5379.
14. (b) Shinkai, S.; Honda, N.; Ishikawa, Y.; Manabe, O. J. Am. Chem. Soc. 1985, 107, 6286.
15. (c) Akiyama, T.; Simeno, F.; Murakami, M.; Yoneda, F. J. Am. Chem. Soc. 1992, 114, 6613.
16. (a) Hasford, J. J.; Kemnitzer, W.; Rizzo, C. J. J. Org. Chem. 1997, 62, 5244.
17. (b) Hasford, J. J.; Rizzo, C. J. Tetrahedron Lett. 1998, 39, in press.
18. (c) Shokat, K. M.; Leumann, C. J.; Sugasawara, R.; Schultz, P. G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1172.
19. (d) Seward, E. M.; Hopkins, R. B.; Sauerer, W.; Tam, S.-W.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 1783.
20. (e) Shinkai, S.; Kawase, A.; Yamaguchi, T.; Manabe, O.; Wada, Y.; Yoneda, F.; Ohta, T.; Nishimoto, K. J. Am. Chem. Soc. 1989, 111, 4928.
21. (a) Breinlinger, E. C.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 1165.
22. (b) Zipplies, M. F.; Staab, H. A. Tetrahedron Lett. 1985, 25, 1035.
23. (c) Zipplies, M. F.; Krieger, C.; Staab, H. A. Tetrahedron Lett. 1983, 24, 1925.
24. Walsh, C.; Fisher, J.; Spencer, R.; Graham, D. W.; Ashton, W. T.; Brown, J.; Brown, R. D.; Rogers, E. F. Biochemistry 1978, 17, 1942.
25. (a) Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien E. J. J. Med. Chem. 1973, 16, 1207.
26. (b) Hine, J. Structural Effects on Equilibria in Organic Chemistry; R. E. Krieger Publishing Co.: Huntington, NY, 1981.
27. (c) Murav, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker, Inc.: New York, 1993; pp 345-348.
28. (a) Lambooy, J. P. Heterocycl. Compd. 1967, 9, 118.
29. (b) Brown, S. A.; Rizzo, C. J. Synth. Commun. 1996, 26, 4065.
30. Bellamy, F. D.; Ou, K. Tetrahedron Lett. 1984, 25, 839.
31. (a) Brockman, R. W.; Pearson, D. E. J. Am. Chem. Soc. 1952, 74, 4128.
32. (b) Zuman, P. Substituent Effects in Organic Polarography; Plenum Press: New York, 1967; pp 43-130.
33. Bard, A. J.; Faulkner, L. R. Electrochemical Methods. Fundamentals and Applications; J. Wiley & Sons: New York, 1980.
34. Bruice, T. C.; Chan, T. W.; Taulane, J. P.; Yokoe, I.; Elliot, D. L.; Williams, R. F.; Novak, M. J. Am. Chem. Soc. 1977, 99, 6713.
35. Zheng, Y.-J.; Ornstein, R. L. J. Am. Chem. Soc. 1996, 118, 9402.
36. (a) Muller, F.; Massey, V. J. Biol. Chem. 1969, 244, 4007.
37. (b) Bruice, T. C.; Main, L.; Smith, S.; Bruice, P. Y. J. Am. Chem. Soc. 1971, 93, 7327.
38. (c) Gumbley, S. J.; Main, L. Tetrahedron Lett. 1976, 3209.
39. (d) Gascoigne, I. M.; Radda, G. K. Biochim. Biophys. Acta 1967, 131, 498.
40. (e) Loechler, E. L.; Hollocher, T. C. J. Am. Chem. Soc. 1975, 97, 3235.
41. Kumar, V.; Woode, K. A.; Bryan, R. F.; Averill, B. A. J. Am. Chem. Soc. 1986, 108, 490.
42. Hall, D. M.; Turner, E. E. J. Chem. Soc. 1945, 699.
43. King, F. E.; Clark-Lewis, J. W. J. Chem. Soc. 1953, 172.
44. (a) Yoneda, F.; Shinozuka, K.; Hiromatsu, K.; Matsushita, R.; Sakuma, Y.; Hamana, M. Chem. Pharm. Bull. 1980, 28, 3576.
45. (b) King, F. E.; Acheson, R. M.; Yorke-Long, A. B. J. Chem. Soc. 1948, 1926.