Photochemical reactions of coenzyme PQQ (pyrroloquinolinequinone) and analogues with benzyl alcohol derivatives via photoinduced electron transfer

Journal of the American Chemical Society

Volumn 122, Issue 35, 2000, Pages 8435-8443

  Fukuzumi, Shunichi ^a   Itoh, Shinobu ^b   Komori, Takashi ^a   Suenobu, Tomoyoshi ^a   Ishida, Akito ^a   Fujitsuka, Mamoru ^c   Ito, Osamu ^c  

^a OSAKA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; BENZENE; BENZYL ALCOHOL DERIVATIVE; CYANIDE; FURAN; OXYGEN; PHANQUINONE; PYRROLOQUINOLINEQUINONE; QUINOLINE DERIVATIVE; QUINONE DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; ELECTRON TRANSPORT; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; PHOTOLYSIS; PHOTOREACTIVITY; PROTON TRANSPORT; QUANTUM CHEMISTRY;

EID: 0033824823     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001351g     Document Type: Article

References (99)

1. Salisbury, S. A.; Forrest, H. S.; Cruse. W. B. T.; Kennard, O. Nature 1979, 280, 843.
2. The presence of PQQ itself in certain enzymes has been disproved, but instead amino acid derived coenzymes such as 6-hydroxydopa (TOPA), tryptophan tryptophylquinone (TTQ), and 2-alkylthiophenol derivative (Tyr-Cys) were found from bovine serum amine oxidase, methylamine dehydrogenase, and galactose oxidase, respectively. See: Principles and Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993.
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. Nishigori, H.; Yasunaga, M.; Mizumura, M.; Lee, J. W.; Iwatsuru, M. Life Sci. 1989, 45, 593.
12. 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) Itoh, S.; Kawakami, H.; Fukuzumi, S. J. Am. Chem. Soc. 1997, 119, 439.
16. (b) Itoh, S.; Kawakami, H.; Fukuzumi, S. Biochemistry 1998, 37, 6562.
17. (a) Ohshiro, Y.; Itoh, S.; Kurokawa, K.; Kato, J.; Hirao, T.; Agawa, T. Tetrahedron Lett. 1983, 24, 3465.
18. (b) Itoh, S.; Kitamura, Y.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1986, 59, 1907.
19. (c) Sleath, P. R.; Noar, J. B.; Eberlein, G. A.; Bruice, T. C. J. Am. Chem. Soc. 1985, 107, 3328.
20. (d) Rodriguez, E. J.; Bruice, T. C. J. Am. Chem. Soc. 1989, 111, 7947.
21. (e) Mure, M.; Itoh, S.; Ohshiro, Y. Chem. Lett. 1989, 1491.
22. (f) Mure, M.; Itoh, S.; Ohshiro, Y. Tetrahedron Lett. 1989, 30, 6875.
23. (g) Itoh, S.; Mure, M.; Ogino, M.; Ohshiro, Y. J. Org. Chem. 1991, 56, 6857.
24. (h) Ohshiro, Y.; Itoh, S. Bioorg. Chem. 1991, 19, 169.
25. (a) Itoh, S.; Kato, N.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1984, 25, 4753.
26. (b) Mure, M.; Suzuki, A.; Itoh, S.; Ohshiro, Y. J. Chem. Soc., Chem. Commun. 1990, 1608.
27. (c) Itoh, S.; Mure, M.; Suzuki, A.; Murao, H.; Ohshiro, Y. J. Chem. Soc., Perkin Trans. 2 1992, 1245.
28. (a) Itoh, S.; Kato, N.; Ohshiro, Y.; Agawa, T. Chem. Lett. 1985, 135.
29. (b) Itoh, S.; Kato, N.; Mure, M.; Ohshiro, Y. Bull. Chem. Soc. Jpn. 1987, 60, 420.
30. Itoh, S.; Mure, M.; Ohshiro, Y. J. Chem. Soc., Chem. Commun. 1987, 1580.
31. (a) Itoh, S.; Kato, J.; Inoue, T.; Kitamura, Y.; Komatsu, M.; Ohshiro, Y. Synthesis 1987, 1067.
32. (b) Itoh, S.; Inoue, T.; Fukui, Y.; Huang, X.; Komatsu, M.; Ohshiro, Y. Chem. Lett. 1990, 1675.
33. (c) Itoh, S.; Fukui, Y.; Ogino, M.; Haranou, S.; Komatsu, M.; Ohshiro, Y. J. Org. Chem. 1992, 57, 2788.
34. (d) Itoh, S.; Fukui, Y.; Haranou, S.; Ogino, M.; Komatsu, M.; Ohshiro, Y. J. Org. Chem. 1992, 57, 4452.
35. (a) Noar, J. B.; Rodriguez, E. J.; Bruice, T. C. J. Am. Chem. Soc. 1985, 107, 7198.
36. (b) Noar, J. B.; Bruice, T. C. J. Org. Chem. 1987, 52, 1942.
37. (a) Heelis, P. F. Chem. Soc. Rev. 1982, 11, 15.
38. (b) Fukuzumi, S.; Tanaka, T. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part C, pp 578-687.
39. (c) Fukuzumi, S. In Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, CT, 1992; pp 67-175.
40. (d) Fukuzumi, S.; Itoh, S. In Advances in Photochemistry; Neckers, D. C., Volman, D. H., von Bünau, G., Eds.; Wiley: New York, 1998; Vol. 25, pp 107-172.
41. Galland, P.; Senger, H. J. Photochem. Photobiol. B 1988, 1, 277.
42. (a) Galland, P.; Senger, H. Photochem. Photobiol. 1988, 48, 811.
43. (b) Galland, P.; Keiner, P.; Dörnemann, D.; Senger, H.; Brodhun, B.; Häder, D.-P. Photochem. Photobiol. 1990, 51, 675.
44. (c) Galland, P.; Eslava, A. P.; Alvarez, M. I. Photochem. Photobiol. 1997, 66, 879.
45. Lenci, F. In Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: Boca Raton, FL, 1995; pp 1445-1449.
46. Tao, N.; Orlando, M.; Hyon, J.-S.; Gross, M.; Song, P.-S. J. Am. Chem. Soc. 1993, 115, 2526.
47. (a) Checcucci, G.; Shoemaker, R. S.; Bini, E.; Cerny, R.; Tao, N.; Hyon, J.-S.; Gioffre, D.; Ghetti, F.; Lenci, F.; Song, P.-S. J. Am. Chem. Soc. 1997, 119, 5762, 9588.
48. (b) Maeda, M.; Naoki, H.; Matsuoka, T.; Kato, Y.; Kotsuki, H.; Utsumi, K.; Tanaka, T. Tetrahedron Lett. 1997, 38, 7411.
49. Spitzner, D.; Höfle, G.; Klein, I.; Pohlan, S.; Ammermann, D.; Jaenicke, L. Tetrahedron Lett. 1998, 39, 4003.
50. (a) Song, P.-S.; Kim, I.-H.; Florell, S.; Tamai, N.; Yamazaki, T.; Yamazaki, I. Biochim. Biophys. Acta 1990, 1040, 58.
51. (b) Cubeddu, R.; Ghetti, F.; Lenci, F.; Ramponi, R.; Taroni, P. Photochem. Photobiol. 1990, 52, 567.
52. (c) Yamazaki, T.; Yamazaki, I.; Nishimura, Y.; Dai, R.; Song, P.-S. Biochim. Biophys. Acta 1993, 1143, 319.
53. (d) Ghetti, F.; Checcucci, G.; Lenci, F.; Heelis, P. F. J. Photochem. Photobiol. B Biol. 1992, 13, 315.
54. (a) Angelini, N.; Quaranta, A.; Checcucci, G.; Song, P.-S.; Lenci, F. Photochem. Photobiol. 1998, 68, 864.
55. (b) Xia, G.; He, X.; Zhou, Y.; Zhang, M.; Shen, T. J. Photochem. Photobiol. A Chem. 1998, 114, 31.
56. (c) Wells, T. A.; Losi, A.; Dai, R.; Scott, P.; Park. S.-M.; Golbeck, J.; Song, P.-S. J. Phys. Chem. 1997, 101, 366, 7460.
57. A preliminary report on the photochemical reaction of PQQ has appeared: Itoh, S.; Komori, T.; Chiba, Y.; Fukuzumi, S.; Ishida, A.; Takamuku, S. J. Chem. Soc., Chem. Commun. 1996, 465.
58. Itoh, S.; Maruta, J.; Fukuzumi, S. J. Chem. Soc., Perkin Trans. 2 1996, 1429.
59. DeSimone, R. E.; Drago, R. S. J. Am. Chem. Soc. 1970, 92, 2343.
60. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Butterworth-Heinemann: Oxford, 1988.
61. Itoh, S.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1986, 59, 1911.
62. For the mechanism of methylhydrazine reduction of PQQ, see: Mure, M.; Nii, K.; Inoue, T.; Itoh, S.; Ohshiro, Y. J. Chem. Soc., Perkin Trans. 2 1990, 315.
63. Hatchard, C. G.; Parker, C. A. Proc. R. Soc. London. Ser. A 1956, 235, 518.
64. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Non-aqueous Systems, Marcel Dekker: New York, 1990.
65. For the catalytic thermal oxidation of THF by oxygen, see: (a) Sen, A.; Lin, M.; Kao, L.-C.; Hutson, A. C. J. Am. Chem. Soc. 1992, 114, 6385. (b) Fazlur-Rahman, A. K.; Tsai, J.-C.; Nicholas, K. M. J. Chem. Soc., Chem. Commun. 1992, 1334. (c) Aresta, M.; Fragale, C.; Quaranta, E.; Tommasi, I. J. Chem. Soc., Chem. Commun. 1992, 315. (d) Hata, E.; Takai, T.; Mukaiyama, T. Chem. Lett. 1993, 1513.
66. For the catalytic thermal oxidation of THF by oxygen, see: (a) Sen, A.; Lin, M.; Kao, L.-C.; Hutson, A. C. J. Am. Chem. Soc. 1992, 114, 6385. (b) Fazlur-Rahman, A. K.; Tsai, J.-C.; Nicholas, K. M. J. Chem. Soc., Chem. Commun. 1992, 1334. (c) Aresta, M.; Fragale, C.; Quaranta, E.; Tommasi, I. J. Chem. Soc., Chem. Commun. 1992, 315. (d) Hata, E.; Takai, T.; Mukaiyama, T. Chem. Lett. 1993, 1513.
67. For the catalytic thermal oxidation of THF by oxygen, see: (a) Sen, A.; Lin, M.; Kao, L.-C.; Hutson, A. C. J. Am. Chem. Soc. 1992, 114, 6385. (b) Fazlur-Rahman, A. K.; Tsai, J.-C.; Nicholas, K. M. J. Chem. Soc., Chem. Commun. 1992, 1334. (c) Aresta, M.; Fragale, C.; Quaranta, E.; Tommasi, I. J. Chem. Soc., Chem. Commun. 1992, 315. (d) Hata, E.; Takai, T.; Mukaiyama, T. Chem. Lett. 1993, 1513.
68. For the catalytic thermal oxidation of THF by oxygen, see: (a) Sen, A.; Lin, M.; Kao, L.-C.; Hutson, A. C. J. Am. Chem. Soc. 1992, 114, 6385. (b) Fazlur-Rahman, A. K.; Tsai, J.-C.; Nicholas, K. M. J. Chem. Soc., Chem. Commun. 1992, 1334. (c) Aresta, M.; Fragale, C.; Quaranta, E.; Tommasi, I. J. Chem. Soc., Chem. Commun. 1992, 315. (d) Hata, E.; Takai, T.; Mukaiyama, T. Chem. Lett. 1993, 1513.
69. Dekker: R. H.; Duine, J. A.; Frank, J.; Verwiel, P. E. J.; Westerling, J. Eur. J. Biochem. 1982, 125, 69.
70. max of PQQTME as compared to the values of other o-quinones may be caused by the lower excitation energy of PQQTME than other o-quinones (see Table 3).
71. Sun, M.; Moore, T. A.; Song, P.-S. J. Am. Chem. Soc. 1972, 94, 1730.
72. Itoh, S.; Kawakami, H.; Fukuzumi, S. J. Am. Chem. Soc. 1998, 120, 7271.
73. Seeley, G. R. Photochem. Photobiol. 1978, 27, 639.
74. Fukuzumi, S.; Kuroda, S. Res. Chem. Intermed. 1999, 25, 789.
75. (a) Rehm, A.; Weller, A. Ber. Bunsen-Ges. Phys. Chem. 1969, 73, 834.
76. (b) Rehm, A.; Weller, A. Isr. J. Chem. 1970, 8, 259.
77. Patz, M.; Mayr, H.; Maruta, J.; Fukuzumi, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1225.
78. Fukuzumi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305.
79. p being sensitive to the steric effects in the radical ion pair.
80. .- in the 250 ns spectrum in Figure 7.
81. max = 430 nm) is red-shifted as compared to that of 2,4-dimethoxybenzyl alcohol radical cation. Bietti, M.; Baciocchi, E.; Steenken, S. J. Phys. Chem. A 1998, 102, 7337.
82. 3PQQTME* at 780 nm.
83. Eckert, T. S.; Bruice, T. C. J. Am. Chem. Soc. 1983, 105, 4431.
84. .-.
85. Evans, D. H.; Griffith, D. A. J. Electroanal. Chem. 1982, 134, 301.
86. .+.
87. (a) Lebeau, E. L.; Meyer, T. J. Inorg. Chem. 1999, 38, 2174.
88. (b) Roecker, L.; Meyer, T. J. J. Am. Chem. Soc. 1987, 709, 746.
89. (a) Lewis, F. D. Acc. Chem. Res. 1986, 19, 401.
90. (b) Wagner, P. J.; Truman, R. J.; Puchalski, A. E.; Wake, R. J. Am. Chem. Soc. 1986, 108, 7727.
91. (c) Wagner, P. J.; Park, B. S. Org. Photochem. 1991, 11, 227.
92. (d) Jones, G., II; Mouli, N. J. Phys. Chem. 1988, 92, 7174.
93. (e) Cermenati, L.; Freccero, M.; Venturello, P.; Albini, A. J. Am. Chem. Soc. 1995, 117, 7869.
94. (a) Okamura, M. Y.; Feher, G. Annu. Rev. Biochem. 1992, 61, 861.
95. (b) Malmström, B. G. Acc. Chem. Res. 1993, 26, 332.
96. (c) Ferguson-Miller, S.; Babcock, G. T. Chem. Rev. 1996, 96, 2889.
97. (d) Hoganson, C. W.; Babcock, G. T. Science 1997, 277, 1953.
98. (e) Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337.
99. Cukier, R. I. J. Phys. Chem. A 1999, 103, 5989.