High-frequency electron paramagnetic resonance spectroscopy of the apogalactose oxidase radical

Journal of Physical Chemistry

Volumn 100, Issue 41, 1996, Pages 16739-16748

  Gerfen, Gary J ^a   Bellew, Brendan F ^a   Griffin, Robert G ^a   Singel, David J ^b   Ekberg, Christopher A ^c   Whittaker, James W ^c  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b MONTANA STATE UNIVERSITY   (United States)

^c OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748447012     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp960709l     Document Type: Article

References (86)

1. Avigad, G.; Amaral, D.; Asensio, C.; Horecker, B. L. J. Biol. Chem. 1962, 237, 2736-2743.
2. Kosman, D. J. In Copper Proteins and Copper Enzymes; Lontie, R., Ed.; CRC Press: Boca Raton, FL, 1984; Vol. 2, pp 1-26.
3. Whittaker, J. W. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Marcel Dekker: Basel, 1994; pp 315-360.
4. Hamilton, G. A.; Adolf, P. K.; de Jersey, J.; DuBois, G. C.; Dyrkacz, G. R.; Libby, R. D. J. Am. Chem. Soc. 1978, 100, 1899.
5. Whittaker, M. M.; Whittaker, J. W. J. Biol. Chem. 1988, 263, 6074-6080.
6. Clark, K.; Penner-Hahn, J. E.; Whittaker, M. M.; Whittaker, J. W. J. Am. Chem. Soc. 1990, 112, 6433-6434.
7. Clark, K.; Penner-Hahn, J. E.; Whittaker, M. M.; Whittaker, J. W. Biochemistry 1994, 33, 12553-12557.
8. Whittaker, M. M.; Whittaker, J. W. J. Biol. Chem. 1990, 265, 9610-9613.
9. Ito, N.; Phillips, S. E. V.; Yadav, K. D. S.; Knowles, P. F. J. Mol. Biol. 1994, 238, 794-814.
10. Babcock, G. T.; El-Deeb, M. K.; Sandusky, P. O.; Whittaker, M. M.; Whittaker, J. W. J. Am. Chem. Soc. 1992, 114, 3727-3734.
11. Prince, R. C. Trends Biochem. Sci. 1988, 13, 286-288.
12. Ehrenberg, A.; Reichard, P. J. Biol. Chem. 1972, 247, 3485-3488.
13. Sahlin, M.; Petersson, L.; Gräslund, A.; Ehrenberg, A.; Sjöberg, B.-M.; Thelander, L. Biochemistry 1987, 26, 5541.
14. Bender, C. J.; Sahlin, M.; Babcock, G. T.; Barry, B. A.; Chandrashekar, T. K.; Salowe, S. P.; Stubbe, J.; Lindström, B.; Petersson, L.; Ehrenberg, A.; Sjöberg, B.-M. J. Am. Chem. Soc. 1989, 111, 8076-8083.
15. Karthein, R.; Dietz, R.; Nastainczyk, W.; Ruf, H. H. Eur. J. Biochem. 1988, 171, 313-320.
16. Lassmann, G.; Odenwaller, R.; Curtis, J. F.; DeGray, J. A.; Mason, R. P.; Marnett, L. J.; Eling, T. E. J. Biol. Chem. 1991, 266, 20045-20055.
17. Barry, B. A.; El-Deeb, M. K.; Sandusky, P. O.; Babcock, G. T. J. Biol. Chem. 1990, 265, 20139-20143.
18. Barry, B. A.; Babcock, G. T. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 7099.
19. Hoganson, C. W.; Babcock, G. T. Biochemistry 1992, 31, 11874-11880.
20. Lane Gilchrist, M., Jr.; Ball, J. A.; Randall, D. W.; Britt, R. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9545-9549.
21. Koulougliotis, D.; Tang, X.-S.; Diner, B. A.; Brudvig, G. W. Biochemistry 1995, 34, 2850-2856.
22. Hori, H.; Yonetani, T. J. Biol. Chem. 1985, 260, 349.
23. Wagner, A. F. V.; Frey, M.; Neugebauer, F. A.; Schäfer, W.; Knappe, J. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 996-1000.
24. Sivaraja, M.; Goodin, D. B.; Smith, M.; Hoffman, B. M. Science 1989, 245, 738-240.
25. Licht, S.; Gerfen, G. J.; Stubbe, J. Science 1996, 271, 477-481.
26. Parast, C. V.; Wong, K. K.; Kozarich, J. W.; Peisach, J.; Magliozzo, R. S. Biochemistry 1995, 34, 5712-5717.
27. Stubbe, J. Annu. Rev. Biochem. 1989, 58, 257-285.
28. Stubbe, J. Biochemistry 1988, 27, 3893-3900.
29. Whittaker, M. M.; Whittaker, J. W. Biophys. J. 1993, 64, 762-772.
30. Branchaud, B. P.; Montague-Smith, M. P.; Kosman, D. J.; McLaren, F. R. J. Am. Chem. Soc. 1993, 115, 798-800.
31. Hoff, A. J., Ed. Advanced EPR: Applications in Biology and Biochemistry; Elsevier: Amsterdam, 1989.
32. Kevan, L., Bowman, M. K., Eds. Modern Pulsed and Continuous Wave Electron Spin Resonance; John Wiley & Sons: New York, 1990.
33. Abragam, A.; Bleaney, B. Electron Paramagnetic Resonance of Transition Ions; Dover: New York, 1970.
34. Evelo, R. G.; Hoff, A. J.; Dikanov, S. A.; Tyrshkin, A. M. Chem. Phys. Lett. 1989, 161, 479-484.
35. Fishel, L. A.; Farnum, M. F.; Mauro, J. M.; Miller, M. A.; Kraut, J.; Liu, Y.; Tan, X.-I.; Scholes, C. P. Biochemistry 1991, 30, 1986-1996.
36. Force, D. A.; Randall, D. W.; Britt, R. D.; Tang, X.-S.; Diner, B. A. J. Am. Chem. Soc. 1995, 117, 12643-12644.
37. Tsvetkov, Y. D. In Proceedings of the International Workshop on Electron Magnetic Resonance of Disordered Systems; Yordanov, N. D., Ed.; World Scientific: Singapore, 1989; pp 15-57.
38. Lebedev, Y. S. In Modern Pulsed and Continuous-Wave Electron Spin Resonance; Kevan, L., Bowman, M. K., Eds.; John Wiley & Sons: New York, 1990; pp 365-404.
39. Gerfen, G. J.; Bellew, B. F.; Un, S.; Joseph, J.; Bollinger, M.; Stubbe, J.; Griffin, R. G.; Singel, D. J. J. Am. Chem. Soc. 1993, 115, 6420-6421.
40. Belford, R. L.; Clarkson, R. B. In Advances in Chemistry Series; Botto, R. E., Sanada, Y., Eds.; American Chemical Society: Washington, DC, 1993; Vol. 229, pp 107-138.
41. Un, S.; Brunel, L.-C.; Brill, T. M.; Zimmermann, J.-L.; Rutherford, A. W. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 5262-5266.
42. Krinichnyi, V. I. 2-mm Wave Band EPR Spectroscopy of Condensed Systems; CRC Press: Boca Raton, FL, 1995.
43. Prisner, T. F.; Est, A. v. d.; Bittl, R.; Lubitz, W.; Stehlik, D.; Möbius, K. Chem. Phys. 1995, 194, 361-370.
44. Disselhorst, J. A. J. M.; Meer, H. v. d.; Poluektov, O. G.; Schmidt, J. J. Magn. Reson. A 1995, 115, 183-188.
45. Gulin, V. I.; Dikanov, S. A.; Tsvetkov, Y. D.; Evelo, R. G.; Hoff, A. J. Pure Appl. Chem. 1992, 64, 903-906.
46. Fasanella, E. L.; Gordy, W. Proc. Natl. Acad. Sci. U.S.A. 1969, 62, 299-304.
47. Itoh, S.; Hirano, K.; Furuta, A.; Komatsu, M.; Ohshiro, Y.; Ishida, A.; Takamuku, S.; Kohzuma, T.; Nakamura, N.; Suzuki, S. Chem. Lett. 1993, 2099-2102.
48. Whittaker, M. M.; DeVito, V. L.; Asher, S. A.; Whittaker, J. W. J. Biol. Chem. 1989, 264, 7104-7106.
49. Whittaker, M. M.; Chuang, Y.-Y.; Whittaker, J. W. J. Am. Chem. Soc. 1993, 115, 10029-10035.
50. Barigelletti, F.; Juris, A.; Balzani, V.; Belser, P.; Zewlewsky, A. v. Inorg. Chem. 1983, 22, 3335-3339.
51. Pilgram, K. H.; Medina, D.; Soloway, S. B.; Gaertner, G. U. Method of Production of Hydroxyaryl Thioehters from Sulfonium Compounds. U.S. Patent 3772391, 1973.
52. Salowe, S. P.; Stubbe, J. J. Bacteriol. 1986, 165, 363-366.
53. Becerra, L.; Gerfen, G.; Bellew, B.; Bryant, J.; Hall, D.; Inati, S.; Weber, R. Un, S.; Prisner, T.; McDermott, A.; Fishbein, K.; Kreischer, K.; Temkin, R.; Singel, D.; Griffin, R. J. Magn. Reson., Ser. A 1995, 117, 28-40.
54. Prisner, T. F.; Un, S.; Griffin, R. G. Isr. J. Chem. 1992, 32, 357-363.
55. van der Donk, W. A.; Stubbe, J.; Gerfen, G. J.; Bellew, B. F.; Griffin, R. G. J. Am. Chem. Soc. 1995, 117, 8908-8916.
56. Hyde, J. S.; Jesmanowiscz, A.; Ratke, J. J.; Antholine, W. E. J. Magn. Reson. 1992, 96, 1-13.
57. Burghaus, O.; Rohrer, M.; Götzinger, T.; Plato, M.; Möbius, K. Meas. Sci. Technol. 1992, 3, 765-774.
58. Ammerlaan, C. A. J.; van der Wiel, A. J. Magn. Reson. 1976, 21, 387-396.
59. Delley, B. J. Chem. Phys. 1990, 92, 508-517.
60. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
61. Becke, A. D. J. Chem. Phys. 1988, 88, 2547.
62. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
63. Baker, J.; Sheiner, A.; Andzelm, J. Chem. Phys. Lett. 1993, 216, 380-388.
64. Lamin, G. J.; Handy, N. C.; Amos, R. D. Mol. Phys. 1993, 80, 1121-1134.
65. Qin, Y.; Wheeler, R. A. J. Chem. Phys. 1995, 102, 1689-1698.
66. VanVleck, J. H. The Theory of Electric and Magnetic Susceptibilities; Oxford University Press: New York, 1965.
67. Stone, A. J. Mol. Phys. 1963, 6, 509-515.
68. Stone, A. J. Mol. Phys. 1964, 7, 311-316.
69. McCain, D. C.; Hayden, D. W. J. Magn. Reson. 1973, 12, 312-330.
70. Prabhananda, B. S.; Felix, C. C.; Hyde, J. S.; Walvekar, A. J. Chem. Phys. 1985, 83, 6121-6127.
71. Burghaus, O.; Plato, M.; Rohrer, M.; Möbius, K.; MacMillan, F.; Lubitz, W. J. Phys. Chem. 1993, 97, 7639-7647.
72. Atkins, P. W.; Symonds, M. C. R. The Structure of Inorganic Radicals; Elsevier: New York, 1967.
73. Mukheerjee, A.; McGlashin, M. L.; Spiro, T. G. J. Chem. Phys. 1995, 99, 4912-4917.
74. Box, H. C.; Budzinski, E. E. J. Chem. Soc., Perkins Trans. 2 1976, 553-555.
75. Preston, K. F.; Sutcliffe, L. H. Magn. Reson. Chem. 1990, 28, 189-204.
76. Kou, W. W. H.; Box, H. C. J. Chem. Phys. 1976, 64, 3060-3062.
77. Box, H. C.; Budzinski, E. E.; Freund, H. G. J. Chem. Phys. 1974, 61, 2222-2226.
78. Carrington, A.; McLachlan, A. D. Introduction to Magnetic Resonance; Harper & Row: New York, 1967.
79. Wertz, J. E.; Bolton, J. R. Electron Spin Resonance: Elementary Theory and Practical Applications.; Chapman and Hall: New York, 1986.
80. McLachlan, A. D. Mol. Phys. 1958, 1, 233-240.
81. Heller, C.; McConnell, H. M. J. Chem. Phys. 1960, 32, 1535-1539.
82. 14 the spin density of 0.08 (Figure 6) on C5 determined by the MO calculation leads to an isotropic hyperfine coupling of approximately 0.2 mT. This is in contrast to the isotropic value of approximately 0.9 mT determined experimentally for the smaller of the two resolved hyperfine interactions. Because the difference in these two values is signficantly greater than that which could arise from uncertainties in the calculated spin densities and in the measured hyperfine coupling constant, we do not assign this hyperfine interaction to the α proton H5.
83. The similarity in g values between the MTC radical and the apogalactose oxidase radical suggests a similarity in electronic structure, and thus equal spin density at C5, for the two species. The chemical similarity of the radicals suggests an equality in McConnell Q values. It thus seems reasonable to expect a similarity in ortho hyperfine interactions between the MTC and apogalactose oxidase radicals.
84. Miura, Y.; Asada, H.; Kinoshita, M.; Ohta, K. J. Phys. Chem. 1983, 87, 3450-3455.
85. 2(π/2-2π/3) ∼ 0.75 for the observed proton. Using eq 6 and again scaling the sulfur spin density from 1 to 0.28 yields the estimate of 0.67 mT for the C8 protons of MTC.
86. Avezoux, A.; Goodwin, M. G.; Anthony, C. Biochem. J. 1995, 307, 735-741.