Ultrafast dynamics of flavins in five redox states

Journal of the American Chemical Society

Volumn 130, Issue 39, 2008, Pages 13132-13139

  Kao, Ya Ting ^a   Saxena, Chaitanya ^a   He, Ting Fang ^a   Guo, Lijun ^a   Wang, Lijuan ^a   Sancar, Aziz ^b   Zhong, Dongping ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENDING MOTION; CHARGE RECOMBINATIONS; CONICAL INTERSECTION; CRYPTOCHROME; DNA REPAIR; EMISSION SPECTRUMS; EXCITED-STATE DYNAMICS; FEMTO-SECOND RESOLUTION; FLAVOENZYME; FUNCTIONAL CHANNELS; INTRA-MOLECULAR ELECTRON TRANSFER; LONG LIFETIME; PHOTOLYASE; PICOSECONDS; PLANAR CONFIGURATIONS; PLANAR STRUCTURE; PLANARITY; REDOX STATE; RING STRUCTURES; SEMIQUINONE RADICALS; SEMIQUINONES; STRONG CORRELATION; SYSTEMATIC STUDY; ULTRA-FAST DYNAMICS; WAVELENGTH DEPENDENCE;

COENZYMES; DYNAMICS; EXCITED STATES; FLEXIBLE STRUCTURES; FREE RADICAL REACTIONS; KETONES; NUCLEIC ACIDS; PHENOLS;

EMISSION SPECTROSCOPY;

ADENINE; DEOXYRIBODIPYRIMIDINE PHOTOLYASE; HYDROQUINONE DERIVATIVE; RIBOFLAVIN DERIVATIVE; FLAVINE ADENINE NUCLEOTIDE; FLAVINE MONONUCLEOTIDE; FLAVOPROTEIN; FREE RADICAL;

ARTICLE; CHEMICAL STRUCTURE; DNA REPAIR; ELECTRON TRANSPORT; FLAME PHOTOMETRY; MOLECULAR DYNAMICS; OXIDATION REDUCTION REACTION; ANIMAL; CHEMISTRY; INSECT; KINETICS; METABOLISM; PHOTOCHEMISTRY; SPECTROFLUOROMETRY;

ANIMALS; FLAVIN MONONUCLEOTIDE; FLAVIN-ADENINE DINUCLEOTIDE; FLAVOPROTEINS; FREE RADICALS; INSECTS; KINETICS; OXIDATION-REDUCTION; PHOTOCHEMISTRY; SPECTROMETRY, FLUORESCENCE;

EID: 58149159934     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8045469     Document Type: Article

References (93)

1. Walsh, C. Acc. Chem. Res. 1980, 13, 148-155.
2. Massey, V.; Hemmerich, P. Biochem. Soc. Trans. 1980, 8, 246-257.
3. Müller, F. The Flavin Redox-System and Its Biological Function. In Topics in Current Chemistry 108; Boschke, F. L., Ed.; Springer-Verlag: Berlin, 1983; pp 71-107.
4. Müller, F., Ed. Chemistry and Biochemistry of Flavoenzymes; CRC Press: Boca Raton, FL, 1990-1991; Vols. I-III.
5. Fraaije, M. W.; Mattevi, A. Trends Biochem. Sci. 2000, 25, 126-132.
6. Massey, V. Biochem. Soc. Trans. 2000, 28, 283-296.
7. Bornemann, S. Nat. Prod. Rep. 2002, 19, 761-772.
8. Joosten, V.; van Berkel, W. J. H. Curr. Opin. Chem. Biol. 2007, 11, 195-202.
9. Susin, S. A.; Lorenzo, H. K.; Zamzami, N.; Marzo, I.; Snow, B. E.; Brothers, G. M.; Mangion, J.; Jacotot, E.; Costantini, P.; Loeffler, M.; Larochette, N.; Goodlett, D. R.; Aebersold, R.; Siderovski, D. P.; Penninger, J. M.; Kroemer, G. Nature 1999, 397, 441-446.
10. Chen, Y.-C.; Lin-Shiau, S.-Y.; Lin, J.-K. J. Cell. Physiol. 1998, 177, 324-333.
11. Dagley, S. Annu. Rev. Microbiol. 1987, 41, 1-23.
12. Chen, H. Z.; Hopper, S. L.; Cerniglia, C. E. Microbiology 2005, 151, 1433-1441.
13. Fitzpatrick, P. F. Acc. Chem. Res. 2001, 34, 299-307.
14. Massey, V. J. Biol. Chem. 1994, 269, 22459-22462.
15. van Pée, K.-H.; Patallo, E. P. Appl. Microbiol. Biotechnol. 2006, 70, 631-641.
16. Dong, C.; Flecks, S.; Unversucht, S.; Haupt, C.; van Pée, K.-H.; Naismith, J. H. Science 2005, 309, 2216-2219.
17. Sancar, A. Chem. Rev. 2003, 103, 2203-2237.
18. Kao, Y.-T.; Saxena, C.; Wang, L.; Sancar, A.; Zhong, D. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 16128-16132.
19. Partch, C. L.; Sancar, A. Photochem. Photobiol. 2005, 81, 1291-1304.
20. Lin, C.; Shalitin, D. Annu. Rev. Plant Biol. 2003, 54, 469-496.
21. Lin, C.; Todo, T. Genome Biol. 2005, 6, 220.1220.9.
22. Kennis, J. T. M.; Groot, M.-L. Curr. Opin. Struct. Biol. 2007, 17, 623-630.
23. Christie, J. M. Annu. Rev. Plant Biol. 2007, 58, 21-45.
24. Heelis, P. F. Chem. Soc. Rev. 1982, 11, 15-39.
25. Ghisla, S.; Massey, V.; Lhoste, J.-M.; Mayhew, S. G. Biochemistry 1974, 13, 589-597.
26. Land, E. J.; Swallow, A. J. Biochemistry 1969, 8, 2117-2125.
27. Sakai, M.; Takahashi, H. J. Mol. Struct. 1996, 379, 9-18.
28. Massey, V.; Palmer, G. Biochemistry 1966, 5, 3181-3189.
29. Li, Y. F.; Sancar, A. Biochemistry 1990, 29, 5698-5706.
30. Kao, Y.-T.; Tan, C.; Song, S.-H.; Öztürk, N.; Li, J.; Wang, L.; Sancar, A.; Zhong, D. J. Am. Chem. Soc. 2008, 130, 7695-7701.
31. Zhong, D.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 11867-11872.
32. Mataga, N.; Chosrowjan, H.; Taniguchi, S.; Tanaka, F.; Kido, N.; Kitamura, M. J. Phys. Chem. B 2002, 106, 8917-8920.
33. Park, H.-W.; Kim, S.-T.; Sancar, A.; Deisenhofer, J. Science 1995, 268, 1866-1872.
34. Li, Y. F.; Heelis, P. F.; Sancar, A. Biochemistry 1991, 30, 6322-6329.
35. Aubert, C.; Vos, M. H.; Mathis, P.; Eker, A. P. M.; Brettel, K. Nature 2000, 405, 586-590.
36. Byrdin, M.; Eker, A. P. M.; Vos, M. H.; Brettel, K. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 8676-8681.
37. Saxena, C.; Sancar, A.; Zhong, D. J. Phys. Chem. B 2004, 108, 18026-18033.
38. Wang, H.; Saxena, C.; Quan, D.; Sancar, A.; Zhong, D. J. Phys. Chem. B 2005, 109, 1329-1333.
39. Gauden, M.; Yeremenko, S.; Laan, W.; van Stokkum, I. H. M.; Ihalainen, J. A.; van Grondelle, R.; Hellingwerf, K. J.; Kennis, J. T. M. Biochemistry 2005, 44, 3653-3662.
40. Kennis, J. T. M.; Crosson, S.; Gauden, M.; van Stokkum, I. H. M.; Moffat, K.; van Grondelle, R. Biochemistry 2003, 42, 3385-3392.
41. Holzer, W.; Penzkofer, A.; Fuhrmann, M.; Hegemann, P. Photochem. Photobiol. 2002, 75, 479-487.
42. Chosrowjan, H.; Taniguchi, S.; Mataga, N.; Tanaka, F.; Visser, A. J. W. G. Chem. Phys. Lett. 2003, 378, 354-358.
43. Stanley, R. J.; MacFarlane, A. W. J. Phys. Chem. A 2000, 104, 6899-6906.
44. Weber, G. Biochem. J. 1950, 47, 114-121.
45. Barrio, J. R.; Tolman, G. L.; Leonard, N. J.; Spencer, R. D.; Weber, G. Proc. Natl. Acad. Sci. U.S.A. 1973, 70, 941-943.
46. van den Berg, P. A. W.; Feenstra, K. A.; Mark, A. E.; Berendsen, H. J. C.; Visser, A. J. W. G. J. Phys. Chem. B 2002, 106, 8858-8869.
47. Li, G.; Glusac, K. D. J. Phys. Chem. A 2008, 112, 4573-4583.
48. Visser, A. J. W. G. Photochem. Photobiol. 1984, 40, 703-706.
49. Visser, A. J. W. G.; Ghisla, S.; Lee, J. Picosecond Fluorescence Dynamics of Reduced Flavins. In Flavins and Flavoproteins 1990; Curti, B., Ronchi, S., Zanetti, G., Eds.; Walter de Gruyter & Co.: Berlin, 1991; pp 49-54.
50. Leenders, R.; Kooijman, M.; van Hoek, A.; Veeger, C.; Visser, A. J. W. G. Eur. J. Biochem. 1993, 211, 37-45.
51. Bruggeman, Y. E.; Schoenmakers, R. G.; Schots, A.; Pap, E. H. W.; van Hoek, A.; Visser, A. J. W. G.; Hilhorst, R. Eur. J. Biochem. 1995, 234, 245-250.
52. Heelis, P. F.; Hartman, R. F.; Rose, S. D. Photochem. Photobiol. 1993, 57, 1053-1055.
53. Enescu, M.; Lindqvist, L.; Soep, B. Photochem. Photobiol. 1998, 68, 150-156.
54. Kim, S.-T.; Heelis, P. F.; Okamura, T.; Hirata, Y.; Mataga, N.; Sancar, A. Biochemistry 1991, 30, 11262-11270.
55. Visser, A. J. W. G.; Ghisla, S.; Massey, V.; Müller, F.; Veeger, C. Eur. J. Biochem. 1979, 101, 13-21.
56. Fox, J. L. FEBS Lett. 1974, 39, 53-55.
57. Müller, F.; Massey, V.; Heizmann, C.; Hemmerich, P.; Lhoste, J.-M.; Gould, D. C. Eur. J. Biochem. 1969, 9, 392-401.
58. Ghisla, S.; Massey, V. J. Biol. Chem. 1975, 250, 577-584.
59. Massey, V.; Stankovich, M.; Hemmerich, P. Biochemistry 1978, 17, 1-8.
60. Swenson, R. P.; Krey, G. D. Biochemistry 1994, 33, 8505-8514.
61. Traber, R.; Kramer, H. E. A.; Hemmerich, P. Biochemistry 1982, 21, 1687-1693.
62. Song, S.-H.; Öztürk, N.; Denaro, T. R.; Arat, N. Ö.; Kao, Y.-T.; Zhu, H.; Zhong, D.; Reppert, S. M.; Sancar, A. J. Biol. Chem. 2007, 282, 17608-17612.
63. Öztürk, N.; Song, S.-H.; Selby, C. P.; Sancar, A. J. Biol. Chem. 2008, 283, 3256-3263.
64. Sancar, A.; Smith, F. W.; Sancar, G. B. J. Biol. Chem. 1984, 259, 6028-6032.
65. Heelis, P. F.; Payne, G.; Sancar, A. Biochemistry 1987, 26, 4634-4640.
66. Malicka, J.; Groth, M.; Karolczak, J.; Czaplewski, C.; Liwo, A.; Wiczk, W. Biopolymers 2001, 58, 447-457.
67. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley-VCH: Weinheim, 2003.
68. Kotowycz, G.; Teng, N.; Klein, M. P.; Calvin, M. J. Biol. Chem. 1969, 244, 5656-5662.
69. Kainosho, M.; Kyogoku, Y. Biochemistry 1972, 11, 741-752.
70. Copeland, R. A.; Spiro, T. G. J. Phys. Chem. 1986, 90, 6648-6654.
71. Weber, G.; Tanaka, F.; Okamoto, B. Y.; Drickamer, H. G. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 1264-1266.
72. Hahn, J.; Michel-Beyerle, M.-E.; Rösch, N. J. Mol. Model. 1998, 4, 73-82.
73. Islam, S. D. M.; Susdorf, T.; Penzkofer, A.; Hegemann, P. Chem. Phys. 2003, 295, 137-149.
74. Moser, C. C.; Keske, J. M.; Warncke, K.; Farid, R. S.; Dutton, P. L. Nature 1992, 355, 796-802.
75. Seidel, C. A. M.; Schulz, A.; Sauer, M. H. M. J. Phys. Chem. 1996, 100, 5541-5553.
76. Lowe, H. J.; Clark, W. M. J. Biol. Chem. 1956, 221, 983-992.
77. Qiu, W.; Kao, Y.-T.; Zhang, L.; Yang, Y.; Wang, L.; Stites, W. E.; Zhong, D.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13979-13984.
78. Zhang, L.; Wang, L.; Kao, Y.-T.; Qiu, W.; Yang, Y.; Okobiah, O.; Zhong, D. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 18461-18466.
79. Jovanovic, S. V.; Simic, M. G. J. Phys. Chem. 1986, 90, 974-978.
80. Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1993, 115, 2437-2440.
81. Wan, C.; Xia, T.; Becker, H.-C.; Zewail, A. H. Chem. Phys. Lett. 2005, 412, 158-163.
82. Partch, C. L.; Clarkson, M. W.; Özgür, S.; Lee, A. L.; Sancar, A. Biochemistry 2005, 44, 3795-3805.
83. Sobolewski, A. L.; Domcke, W. Eur. Phys. J. D 2002, 20, 369-374.
84. Levine, B. G.; Martínez, T. J. Annu. Rev. Phys. Chem. 2007, 58, 613-634.
85. Lennon, B. W.; Williams, C. H., Jr.; Ludwig, M. L. Protein Sci. 1999, 8, 2366-2379.
86. Moonen, C. T. W.; Vervoort, J.; Müller, F. Biochemistry 1984, 23, 4859-4867.
87. Moonen, C. T. W.; Vervoort, J.; Müller, F. Biochemistry 1984, 23, 4868-4872.
88. Dixon, D. A.; Lindner, D. L.; Branchaud, B.; Lipscomb, W. N. Biochemistry 1979, 18, 5770-5775.
89. Zheng, Y.-J.; Ornstein, R. L. J. Am. Chem. Soc. 1996, 118, 9402-9408.
90. Hasford, J. J.; Kemnitzer, W.; Rizzo, C. J. J. Org. Chem. 1997, 62, 5244-5245.
91. Rodríguez-Otero, J.; Martínez-Núñez, E.; Peña-Gallego, A.; Vázquez, S. A. J. Org. Chem. 2002, 67, 6347-6352.
92. Climent, T.; González-Luque, R.; Merchán, M.; Serrano-Andrés, L. J. Phys. Chem. A 2006, 110, 13584-13590.
93. Choe, Y.-K.; Nagase, S.; Nishimoto, K. J. Comput. Chem. 2007, 28, 727-739.