Electrochemical behavior and characterization of semiquinone radical anion species of coenzyme PQQ in aprotic organic media

Journal of the American Chemical Society

Volumn 120, Issue 29, 1998, Pages 7271-7277

  Itoh, Shinobu ^a   Kawakami, Hirokatsu ^a   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SEMIQUINONE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; ELECTRON SPIN RESONANCE; OXIDATION; OXIDATION REDUCTION REACTION; STOICHIOMETRY;

EID: 0032578160     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9813663     Document Type: Article

References (55)

1. Anthony, C. In Principles and Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993; pp 17-45.
2. Matsushita, K.; Adachi, O. In Principles and Applications of Quinoproteins: Davidson, V. L., Ed.: Marcel Dekker: New York, 1993; pp 47-71.
3. (a) Ameyama, M.; Shinagawa, E.; Matsushita, K.; Adachi, O. Agric. Biol. Chem. 1984, 48, 2909.
4. (b) Shimao, M.; Yamamoto, H.; Ninomiya, K.; Kato, N.; Adachi, O.; Ameyama, M.; Sakazawa, C. Agric. Biol. Chem. 1984, 48, 2873.
5. (c) Ameyama, M.; Shinagawa, E.; Matsushita, K.; Adachi, O. Agric. Biol. Chem. 1984, 48, 3099.
6. (d) Ameyama, M.; Shinagawa, E.; Matsushita, K.; Adachi, O. Agric. Biol. Chem. 1985, 49, 699.
7. (e) Ameyama, M.; Matsushita, K.; Shinagawa, E.; Hayashi, M.; Adachi, O. BioFactors 1988, 1, 51.
8. (f) Adachi, O.; Okamoto, K.; Matsushita, K.; Shinagawa, E.; Ameyama, M. Agric. Biol. Chem. 1990, 54, 2751.
9. (a) Watanabe, A.; Hobara, N.; Tsuji, T. Curr. Ther. Res. 1988, 44, 896.
10. (b) Watanabe, A.; Hobara, N.; Ohsawa, T.; Higashi, T.; Tsuji, T. Hiroshima J. Med. Sci. 1989, 38, 49.
11. (c) Nishigori, H.; Yasunaga, M.; Mizumura M.; Lee, J. W.; Iwatsuru, M. Life Sci. 1989, 45, 593.
12. (d) Hamagishi, Y.; Murata, S.; Kamei, H.; Oki, T.; Adachi, O.; Ameyama, M. J. Pharmacol. Exp. Ther. 1990, 255, 980.
13. (a) Killgore, J.; Smidt, C.; Duich, L.; Romero-Chapman, N.; Tinker, D.; Reiser, K.; Melko, M.; Hyde. D.; Rucker, R. B. Science 1989, 245, 850.
14. (b) Smidt, C. R.; Steinberg, F. M.; Rucker, R. B. Proc. Soc. Exp. Biol. Med. 1991, 197, 19.
15. (a) Lion-Dagan, M.; Katz, E.; Willner, I. J. Am. Chem. Soc. 1994, 116, 7913.
16. (b) Katz, E.; Lötzbeyer, T.; Schlereth, D. D.; Schuhmann, W.; Schmidt, H.-L. J. Electroanal. Chem. 1994, 373, 189.
17. (c) Katz, E.; Lion-Dagan, M.; Willner, I. J. Electroanal. Chem. 1995, 382, 25.
18. (d) Bardea, A.; Katz, E.; Bückmann, A. F.; Willner, I. J. Am. Chem. Soc. 1997, 119, 9114.
19. (e) Esaka, Y.; Kano, K.; Sukeguchi, M.; Goto, M. Anal. Sci. 1993, 9, 207.
20. (f) Kuwabata, S.; Tsuda, R.; Yoneyama, H. J. Am. Chem. Soc. 1994, 116, 5437.
21. (a) Hirao, T.; Murakami, T.; Ohno, M.; Ohshiro, Y. Chem. Lett. 1989, 785.
22. (b) Hirao, T.; Ohno, M.; Ohshiro, Y. Tetrahedron Lett. 1990, 31, 6039.
23. Hirao, T.; Murakami, T.; Ohno, M.; Ohshiro, Y. Chem. Lett. 1991, 299.
24. (a) Itoh, S.; Mure, M.; Ogino, M.; Ohshiro, Y. J. Org. Chem. 1991, 56, 6857.
25. (b) Itoh, S.; Mure, M.; Suzuki, A.; Murao, H.; Ohshiro, Y. J. Chem. Soc., Perkin Trans. 2 1992, 1245.
26. (a) Itoh, S.; Kato, J.; Inoue, T.; Kitamura, Y.; Komatsu, M.; Ohshiro, Y. Synthesis 1987, 1067-1071.
27. (b) Itoh, S.; Fukui, Y.; Ogino, M.; Haranou, S.; Komatsu, M.; Ohshiro, Y. J. Org. Chem. 1992, 57, 2788.
28. Itoh, S.; Fukui, Y.; Haranou, S.; Ogino, M.; Komatsu, M.; Ohshiro, Y. J. Org. Chem. 1992, 57, 4452.
29. (a) Itoh, S.; Ogino, M.; Fukui, Y.; Murao, H.; Komatsu, M.; Ohshiro, Y.; Inoue, T.; Kai, Y.; Kasai, N. J. Am. Chem. Soc. 1993, 115, 9960.
30. (b) Itoh, S.; Kawakami, H.; Fukuzumi, S. J. Am. Chem. Soc. 1997, 119, 439.
31. (c) Itoh, S.; Kawakami, H.; Fukuzumi, S. Biochemistry 1998, 37, 6562.
32. (a) Kano, K.; Mori, K.; Uno, B.; Kubota, T.; Ikeda, T.; Senda, M. Bioelectrochem. Bioenerg. 1990, 24, 193.
33. (b) Kano, K.; Mori, K.; Uno, B.; Kubota, T.; Ikeda, T.; Senda, M. Bioelectrochem. Bioenerg. 1990, 23, 227.
34. Duine et al. determined the redox potential of the quinone/quinol couple as 90 mV vs NHE at pH 7.0 by a potentiometric titration: Duine, J. A.; Frank, J.; Verwiel, P. E. J. Eur. J. Biochem. 1981, 118, 395.
35. Eckert, T. S.; Bruice, T. C.; Gainor, J. A.; Weinreb, S. M. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 2533.
36. (a) White, S.; Boyd, G.; Mathews, F. S.; Xia, Z.-x.; Dai, W.-w.; Zhang, Y.-f.; Davidson, V. L. Biochemistry 1993, 32, 12955.
37. (b) Xia, Z.-x.; Dai, W.-w.; Zhang, Y.-f.; White, S. A.; Boyd, G. D.; Mathews, F. S. J. Mol. Biol. 1996, 259, 480.
38. (a) Blake, C. C. F.; Ghosh, M.; Harlos, K.; Avezoux, A.; Anthony, C. Nat. Struct. Biol. 1994, 1, 102.
39. (b) Cozier, G. E.; Giles, I. G.; Anthony, C. Biochem. J. 1995, 308, 375.
40. (c) Ghosh, M.; Anthony, C.; Harlos, K.; Goodwin, M. G.; Blake, C. Structure 1995, 3, 177.
41. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press: Elmsford, NY, 1966.
42. Ohya-Hishiguchi, H. Bull. Chem. Soc. Jpn. 1979, 52, 2064.
43. 9a an easier way for the preparation of the synthetic intermediate 3 has been developed in this study.
44. The starting material 2 was synthesized by the reported procedures; Corey, E. J.; Tramontano. A. J. Am. Chem. Soc. 1981, 103, 5599.
45. 2.
46. 8a
47. 2.
48. oxH, respectively; Itoh, S.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1986, 59, 1911.
49. Niemz, A.; Imbriglio, J.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 887.
50. Staples, T. L.; Szwarc, M. J. Am. Chem. Soc. 1970, 92, 5022.
51. Rodriguez, E. J.; Bruice, T. C.; Edmondson, D. E. J. Am. Chem. Soc. 1987, 109, 532.
52. (a) Swarz, H. M.; Bolton, J. R.; Borg, D. C. Biological Applicaton of Electron Spin Resonance; John Wiley & Sons: New York, 1972; p 24.
53. (b) Fukuzumi, S.; Nishizawa, N.; Tanaka, T. J. Org. Chem. 1984, 49, 3571.
54. H(8) can also be assigned based on the significantly larger spin density on C(3) than C(8) (see Supporting Information, Figures S3-S5).
55. The redox potentials measured vs ferrocene/ferrocenium are converted to those vs SCE by adding 0.37 V.