Moving Protons and Electrons in Biomimetic Systems

Biochemistry

Volumn 54, Issue 10, 2015, Pages 1863-1878

  Warren, Jeffrey J ^a   Mayer, James M ^b  

^a SIMON FRASER UNIVERSITY   (Canada)

^b YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; BIOMIMETICS; INTERFACES (MATERIALS); PROTONS;

BIOMIMETIC MODEL; BIOMIMETIC SYSTEMS; ENZYME ACTIVE SITES; HYDROGEN ATOMS; MODEL REACTIONS; PROTEIN INTERFACES; PROTON COUPLED ELECTRON TRANSFER REACTIONS; WAYS OF THINKING;

REDOX REACTIONS;

ANTIOXIDANT; CARBON; CYTOCHROME C OXIDASE; HYDROGEN; HYDROXYLAMINE; IRON; MANGANESE; MANGANESE SUPEROXIDE DISMUTASE; PHENOL DERIVATIVE; PORPHYRIN; PROTOPORPHYRIN; QUINONE DERIVATIVE; RIBONUCLEOTIDE REDUCTASE; TRANSITION ELEMENT; BIOMIMETIC MATERIAL; PROTON;

ARTICLE; DISSOCIATION; ELECTRON TRANSPORT; ENERGY TRANSFER; ENTHALPY; ENZYME ACTIVE SITE; EQUILIBRIUM CONSTANT; HYDROGEN BOND; INORGANIC CHEMISTRY; LIPID BILAYER; MOLECULAR DOCKING; MOLECULAR MODEL; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROTON COUPLED ELECTRON TRANSFER; PROTON TRANSPORT; THERMODYNAMICS; TRANSPORT KINETICS; CHEMISTRY; ELECTRON;

BIOMIMETIC MATERIALS; ELECTRON TRANSPORT; ELECTRONS; PROTONS;

EID: 84925266590     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/acs.biochem.5b00025     Document Type: Article

References (263)

1. Orna, M. V. and Stock, J. (1989) Electrochemistry, past and present, American Chemical Society, Washington, DC.
2. Pourbaix, M. (1974) Atlas of Electrochemical Equilibria in Aqueous Solutions, 2nd English ed., National Association of Corrosion Engineers, Houston.
3. Kochi, J. K., Ed. (1973) Free Radicals, Wiley, New York.
4. Anslyn, E. V. and Dougherty, D. A. (2006) Modern Physical Organic Chemistry, University Science Books, Sausalito, CA.
5. Wiberg, K. B. and Evans, R. J. (1960) Tetrahedron 8, 313
6. Eberson, L. and Wistrand, L.-G. (1980) Acta Chem. Scand. B34, 349-357
7. Eberson, L. (1983) J. Am. Chem. Soc. 105, 3192-3199
8. Binstead, R. A., Moyer, B. A., Samuels, G. J., and Meyer, T. J. (1981) J. Am. Chem. Soc. 103, 2897-2899
9. Proton-Coupled Electron Transfer Themed Issue. Chem. Rev. 2010, 110, 6937-7100.
10. Formosinho, S. and Barroso, M., Eds. (2012) Proton-coupled Electron Transfer: A Carrefour for Chemical Reactivity Traditions, Royal Society of Chemistry, Cambridge, U.K.
11. Dempsey, J. L., Winkler, J. R., and Gray, H. B. (2010) Chem. Rev. 110, 7024-7039
12. Marcus, R. A. and Sutin, N. (1985) Biochim. Biophys. Acta 811, 265-322
13. Jiang, W., Yun, D., Saleh, L., Barr, E. W., Xing, G., Hoffart, L. M., Maslak, M.-A., Krebs, C., and Bollinger, J. M. (2007) Science 316, 1188-1191
14. Jiang, W., Saleh, L., Barr, E. W., Xie, J., Gardner, M. M., Krebs, C., and Bollinger, J. M. (2008) Biochemistry 47, 8477-8484
15. Kwak, Y., Jiang, W., Dassama, L. M. K., Park, K., Bell, C. B., Liu, L. V., Wong, S. D., Saito, M., Kobayashi, Y., Kitao, S., Seto, M., Yoda, Y., Alp, E. E., Zhao, J., Bollinger, J. M., Krebs, C., and Solomon, E. I. (2013) J. Am. Chem. Soc. 135, 17573-17584
16. Uhlin, U. and Eklund, H. (1994) Nature 370, 533-539
17. Yokoyama, K., Uhlin, U., and Stubbe, J. (2010) J. Am. Chem. Soc. 132, 15368-15379
18. Yokoyama, K., Uhlin, U., and Stubbe, J. (2010) J. Am. Chem. Soc. 132, 8385-8397
19. Yokoyama, K., Smith, A. A., Corzilius, B., Griffin, R. G., and Stubbe, J. (2011) J. Am. Chem. Soc. 133, 18420-18432
20. Minnihan, E. C., Seyedsayamdost, M. R., Uhlin, U., and Stubbe, J. (2011) J. Am. Chem. Soc. 133, 9430-9440
21. Stubbe, J. (2003) Curr. Opin. Chem. Biol. 7, 183-188
22. Hosler, J. P., Ferguson-Miller, S., and Mills, D. A. (2006) Annu. Rev. Biochem. 75, 165-187
23. von Ballmoos, C., Ädelroth, P., Gennis, R. B., and Brzezinski, P. (2012) Biochim. Biophys. Acta 1817, 650-657
24. Kaila, V. R. I., Verkhovsky, M. I., and Wikström, M. (2010) Chem. Rev. 110, 7062-7081
25. Ishigami, I., Hikita, M., Egawa, T., Yeh, S.-R., and Rousseau, D. L. (2015) Biochim. Biophys. Acta 1847, 98-108
26. Muresanu, L., Pristovsek, P., Löhr, F., Maneg, O., Mukrasch, M. D., Rüterjans, H., Ludwig, B., and Lücke, C. (2006) J. Biol. Chem. 281, 14503-14513
27. Muramoto, K., Hirata, K., Shinzawa-Itoh, K., Yoko-o, S., Yamashita, E., Aoyama, H., Tsukihara, T., and Yoshikawa, S. (2007) Proc. Natl. Acad. Sci. U.S.A. 104, 7881-7886
28. Warren, J. J., Tronic, T. A., and Mayer, J. M. (2010) Chem. Rev. 110, 6961-7001
29. Weinberg, D. R., Gagliardi, C. J., Hull, J. F., Murphy, C. F., Kent, C. A., Westlake, B. C., Paul, A., Ess, D. H., McCafferty, D. G., and Meyer, T. J. (2012) Chem. Rev. 112, 4016-4093
30. Njus, D., Jalukar, V., Zu, J., and Kelley, P. M. (1991) Am. J. Clin. Nutr. 54, 1179S-1183S
31. Jalukar, V., Kelley, P. M., and Njus, D. (1991) J. Biol. Chem. 11, 6878-6882
32. Njus, D. and Kelley, P. M. (1993) Biochim. Biophys. Acta 1144, 235-248
33. Njus, D., Wigle, M., Kelley, P. M., Kipp, B. H., and Schlegel, H. B. (2001) Biochemistry 40, 11905-11911
34. Sjödin, M., Styring, S., Wolpher, H., Xu, Y., Sun, L., and Hammarström, L. (2005) J. Am. Chem. Soc. 127, 3855-3863
35. Mayer, J. M., Hrovat, D. A., Thomas, J. L., and Borden, W. T. (2002) J. Am. Chem. Soc. 124, 11142-11147
36. Isborn, C., Hrovat, D. A., Borden, W. T., Mayer, J. M., and Carpenter, B. K. (2005) J. Am. Chem. Soc. 127, 5794-5795
37. Lingwood, M., Hammond, J. R., Hrovat, D. A., Mayer, J. M., and Borden, W. T. (2006) J. Chem. Theory Comput. 2, 740-745
38. Tishchenko, O., Truhlar, D. G., Ceulemans, A., and Nguyen, M. T. (2008) J. Am. Chem. Soc. 130, 7000-7010
39. Cembran, A., Provorse, M. R., Wang, C., Wu, W., and Gao, J. (2012) J. Chem. Theory Comput. 8, 4347-4358
40. Hammes-Schiffer, S. (2011) J. Phys. Chem. Lett. 2, 1410-1416
41. Reece, S. Y. and Nocera, D. G. (2009) Annu. Rev. Biochem. 78, 673-699
42. Umena, Y., Kawakami, K., Shen, J.-R., and Kamiya, N. (2011) Nature 473, 55-60
43. Waidmann, C. R., Miller, A. J. M., Ng, C.-W. A., Scheuermann, M. L., Porter, T. R., Tronic, T. A., and Mayer, J. M. (2012) Energy Environ. Sci. 5, 7771-7780
44. Bordwell, F. G. and Bausch, M. J. (1986) J. Am. Chem. Soc. 108, 1979-1985
45. Mader, E. A., Manner, V. W., Markle, T. F., Wu, A., Franz, J. A., and Mayer, J. M. (2009) J. Am. Chem. Soc. 131, 4335-4345
46. Mader, E. A., Davidson, E. R., and Mayer, J. M. (2007) J. Am. Chem. Soc. 129, 5153-5166
47. Tilset, M. (2001) in Electron Transfer in Chemistry (Balzani, V., Ed.) pp 677-713, Wiley-VCH, Weinheim, Germany.
48. Waidmann, C. R., Miller, A. J. M., Ng, C.-W. A., Scheuermann, M. L., Porter, T. R., Tronic, T. A., and Mayer, J. M. (2012) Energy Environ. Sci. 5, 7771-7780
49. • and can be evaluated given the same equation 2.
50. An intermediate is typically defined as a species that is a minimum on the free energy surface and that lives for multiple vibrational periods.
51. Roth, J. P., Lovell, S., and Mayer, J. M. (2000) J. Am. Chem. Soc. 122, 5486-5498
52. Yoder, J. C., Roth, J. P., Gussenhoven, E. M., Larsen, A. S., and Mayer, J. M. (2003) J. Am. Chem. Soc. 125, 2629-2640
53. Song, J. S., Bullock, R. M., and Creutz, C. (1991) J. Am. Chem. Soc. 113, 9862-9864
54. Protasiewicz, J. D. and Theopold, K. H. (1993) J. Am. Chem. Soc. 115, 5559-5569
55. Bullock, R. M. (1991) Comments Inorg. Chem. 12, 1-33
56. Newton, M. D. and Sutin, N. (1984) Annu. Rev. Phys. Chem. 35, 437-480
57. Beratan, D. N., Skourtis, S. S., Balabin, I. A., Balaeff, A., Keinan, S., Venkatramani, R., and Xiao, D. (2009) Acc. Chem. Res. 42, 1669-1678
58. Litwinienko, G. and Ingold, K. U. (2003) J. Org. Chem. 68, 3433-3438
59. Litwinienko, G. and Ingold, K. U. (2004) J. Org. Chem. 69, 5888-5896
60. Litwinienko, G. and Ingold, K. U. (2005) J. Org. Chem. 70, 8982-8990
61. Litwinienko, G. and Ingold, K. U. (2007) Acc. Chem. Res. 40, 222-230
62. Warren, J. J. and Mayer, J. M. (2010) Proc. Natl. Acad. Sci. U.S.A. 107, 5282-5287
63. Nakanishi, N., Takeuchi, F., and Tsubaki, M. (2007) J. Biochem. 142, 553-560
64. Warren, J. J. and Mayer, J. M. (2010) J. Am. Chem. Soc. 132, 7784-7793
65. Rhile, I. J., Markle, T. F., Nagao, H., DiPasquale, A. G., Lam, O. P., Lockwood, M. A., Rotter, K., and Mayer, J. M. (2006) J. Am. Chem. Soc. 128, 6075-6088
66. Markle, T. F., Rhile, I. J., DiPasquale, A. G., and Mayer, J. M. (2008) Proc. Natl. Acad. Sci. U.S.A. 105, 8185-8190
67. Markle, T. F., Tronic, T. A., DiPasquale, A. G., Kaminsky, W., and Mayer, J. M. (2012) J. Phys. Chem. A 116, 12249-12259
68. Sjödin, M., Irebo, T., Utas, J. E., Lind, J., Merényi, G., Åkermark, B., and Hammarström, L. (2006) J. Am. Chem. Soc. 128, 13076-13083
69. Zhang, M.-T., Irebo, T., Johansson, O., and Hammarström, L. (2011) J. Am. Chem. Soc. 133, 13224-13227
70. Costentin, C., Robert, M., and Savéant, J.-M. (2007) J. Am. Chem. Soc. 129, 9953-9963
71. Costentin, C., Hajj, V., Robert, M., Savéant, J.-M., and Tard, C. (2011) Proc. Natl. Acad. Sci. U.S.A. 108, 8559-8564
72. Borovik, A. S. (2005) Acc. Chem. Res. 38, 54-61
73. Collman, J. P. and Fu, L. (1999) Acc. Chem. Res. 32, 455-463
74. Siegbahn, P. E. M., Margareta, R. A., and Blomberg, M. R. A. (2010) Chem. Rev. 110, 7040-7061
75. Hammes-Schiffer, S. and Soudackov, A. V. (2008) J. Phys. Chem. B 112, 14108-14123
76. Hammes-Schiffer, S. and Stuchebrukhov, A. A. (2010) Chem. Rev. 110, 6939-6960
77. Tishchenko, O., Truhlar, D. G., Ceulemans, A., and Nguyen, M. T. (2008) J. Am. Chem. Soc. 130, 7000-7010
78. Cukier, R. I. and Nocera, D. G. (1998) Annu. Rev. Phys. Chem. 49, 337-369
79. Jackson, R. A. and O'Neill, D. W. (1969) J. Chem. Soc., Chem. Commun. 1210-1211
80. Foti, M., Ingold, K. U., and Lusztyk, J. (1994) J. Am. Chem. Soc. 116, 9440-9447
81. Kochi, J. K. (1991) Electron-Transfer Oxidation. In Comprehensive Organic Synthesis (Trost, B. M., Ed.) Pergamon, New York.
82. Matsuo, T. and Mayer, J. M. (2005) Inorg. Chem. 44, 2150-2158
83. Hirst, J. (2013) Annu. Rev. Biochem. 82, 551-575
84. DuBois, D. L. and Berning, D. E. (2000) Appl. Organometal. Chem. 14, 860-862
85. Ellis, W. W., Raebiger, J. W., Curtis, C. J., Bruno, J. W., and DuBois, D. L. (2004) J. Am. Chem. Soc. 126, 2738-2743
86. Cheng, J.-P. and Lu, Y. (1997) J. Phys. Org. Chem. 10, 577-584
87. Cheng, J.-P., Lu, Y., Zhu, X., and Mu, L. (1998) J. Org. Chem. 63, 6108-6114
88. Farrington, J. A., Land, E. J., and Swallow, A. J. (1980) Biochim. Biophys. Acta 590, 273
89. Carlson, B. W., Miller, L. L., Neta, P., and Grodkowski, J. (1984) J. Am. Chem. Soc. 106, 7233
90. Zhu, X.-C., Yang, Y., Zhang, M., and Cheng, J.-P. (2003) J. Am. Chem. Soc. 125, 15298
91. Matsuo, T. and Mayer, J. M. (2005) Inorg. Chem. 44, 2150-2158 and references therein
92. Minnihan, E. C., Nocera, D. G., and Stubbe, J. (2013) Acc. Chem. Res. 46, 2524-2535
93. McEvoy, J. P. and Brudvig, G. W. (2006) Chem. Rev. 106, 4455-4483
94. Siegbahn, P. E. M. (2009) Dalton Trans. 45, 10063-10068
95. Smith, W. L., Urade, Y., and Jakobsson, P.-J. (2011) Chem. Rev. 111, 5821-5865
96. Giulivi, C., Traaseth, N. J., and Davies, K. J. A. (2003) Amino Acids 25, 227-232
97. Heinecke, J. W. (2002) Free Radical Biol. Med. 32, 1090-1101
98. Bordwell, F. G. and Cheng, J. (1991) J. Am. Chem. Soc. 113, 1736-1743
99. Lind, J., Shen, X., Eriksen, T. E., and Merenyi, G. (1990) J. Am. Chem. Soc. 112, 479-482
100. Steenken, S. and Neta, P. (1982) J. Phys. Chem. 86, 3661-3667
101. Neta, P. and Grodkowski, J. (2005) J. Phys. Chem. Ref. Data 34, 109-199
102. Bronner, C. and Wenger, O. S. (2014) Phys. Chem. Chem. Phys. 16, 3617-3622
103. Irebo, T., Zhang, M.-T., Markle, T. F., Scott, A. M., and Hammarström, L. (2012) J. Am. Chem. Soc. 134, 16247-16254
104. Song, N. and Stanbury, D. M. (2008) Inorg. Chem. 47, 11458-11460
105. Song, N. and Stanbury, D. M. (2012) Inorg. Chem. 51, 4909-4911
106. Osako, T., Ohkubo, K., Taki, M., Tachi, Y., Fukuzumi, S., and Itoh, S. (2003) J. Am. Chem. Soc. 125, 11027-11033
107. Costentin, C., Louault, C., Robert, M., and Savéant, J.-M. (2009) Proc. Natl. Acad. Sci. U.S.A. 106, 18143-18148
108. Fecenko, C. J., Thorp, H. H., and Meyer, T. J. (2007) J. Am. Chem. Soc. 129, 15098-15099
109. Fecenko, C. J., Meyer, T. J., and Thorp, H. H. (2006) J. Am. Chem. Soc. 128, 11020-11021
110. Bonin, J., Costentin, C., Louault, C., Robert, M., Routier, M., and Savéant, J.-M. (2010) Proc. Natl. Acad. Sci. U.S.A. 107, 3367-3372
111. Glover, S. D., Jorge, C., Liang, L., Valentine, K. G., Hammarström, L., and Tommos, C. (2014) J. Am. Chem. Soc. 136, 14039-14051
112. Reece, S. Y. and Nocera, D. G. (2005) J. Am. Chem. Soc. 127, 9448-9458
113. Sjödin, M., Styring, S., Kermark, B., Sun, L., and Hammarström, L. (2000) J. Am. Chem. Soc. 122, 3932-3936
114. Irebo, T., Reece, S. Y., Sjoedin, M., Nocera, D. G., and Hammarström, L. (2007) J. Am. Chem. Soc. 129, 15462-15464
115. Cape, J. L., Bowman, M. K., and Kramer, D. M. (2005) J. Am. Chem. Soc. 127, 4208-4215
116. Westlake, B. C., Brennaman, M. K., Concepcion, J. J., Paul, J. J., Bettis, S. E., Hampton, S. D., Miller, S. A., Lebedeva, N. V., Forbes, M. D. E., Moran, A. M., Meyer, T. J., and Papanikolas, J. M. (2011) Proc. Natl. Acad. Sci. U.S.A. 108, 8554-8558
117. Eisenhart, T. T. and Dempsey, J. L. (2014) J. Am. Chem. Soc. 136, 12221-12224
118. Wenger, O. S. (2015) Coord. Chem. Rev. 282-283, 150-158
119. Chen, J., Kuss-Petermann, M., and Wenger, O. S. (2015) J. Phys. Chem. B 119, 2263-2273
120. Gagliardi, C. J., Westlake, B. C., Kent, C. A., Paul, J. J., Papanikolas, J. M., and Meyer, T. J. (2010) Coord. Chem. Rev. 254, 2459-2471
121. Lebedeva, N. V., Schmidt, R. D., Concepcion, J. J., Brennaman, M. K., Stanton, I. N., Therien, M. J., Meyer, T. J., and Forbes, M. D. E. (2011) J. Phys. Chem. A 115, 3346-3356
122. Gupta, N., Linschitz, H., and Biczok, L. (1997) Fullerene Sci. Technol. 5, 343-353
123. Biczok, L., Gupta, N., and Linschitz, H. (1997) J. Am. Chem. Soc. 119, 12601-12609
124. Maki, T., Araki, Y., Ishida, Y., Onomura, O., and Matsumura, Y. (2001) J. Am. Chem. Soc. 123, 3371-3372
125. Benisvy, L., Blake, A. J., Collison, D., Davies, E. S., Garner, C. D., McInnes, E. J. L., McMaster, J., Whittaker, G., and Wilson, C. (2003) J. Chem. Soc., Dalton Trans. 1975-1985
126. Benisvy, L., Bill, E., Blake, A. J., Collison, D., Davies, E. S., Garner, C. D., Guindy, C. I., McInnes, E. J. L., McArdle, G., McMaster, J., Wilson, C., and Wolowska, J. (2004) Dalton Trans. 3647-3653
127. Stubbe, J., Nocera, D. G., Yee, C. S., and Chang, M. C. Y. (2003) Chem. Rev. 103, 2167-2201
128. Rhile, I. J., Markle, T. F., Nagao, H., DiPasquale, A. G., Lam, O. P., Lockwood, M. A., Rotter, K., and Mayer, J. M. (2006) J. Am. Chem. Soc. 128, 6075-6088
129. Schrauben, J. N., Cattaneo, M., Day, T. C., Tenderholt, A. L., and Mayer, J. M. (2012) J. Am. Chem. Soc. 134, 16635-16645
130. Markle, T. F., Tronic, T. A., DiPasquale, A. G., Kaminsky, W., and Mayer, J. M. (2012) J. Phys. Chem. A 116, 12249-12259
131. Bonin, J., Costentin, C., Robert, M., and Savéant, J.-M. (2011) Org. Biomol. Chem. 9, 4064-4069
132. Markle, T. F., Rhile, I. J., DiPasquale, A. G., and Mayer, J. M. (2008) Proc. Natl. Acad. Sci. U.S.A. 105, 8185-8190
133. Markle, T. F. and Mayer, J. M. (2008) Angew. Chem., Int. Ed. 47, 738-740
134. Markle, T. F., Rhile, I. J., and Mayer, J. M. (2011) J. Am. Chem. Soc. 133, 17341-17352
135. Zhang, M.-T., Irebo, T., Johansson, O., and Hammarström, L. (2011) J. Am. Chem. Soc. 133, 13224-13227
136. Johannissen, L. O., Irebo, T., Sjödin, M., Johansson, O., and Hammarström, L. (2009) J. Phys. Chem. B 113, 16214-16225
137. Markle, T. F., Tenderholt, A. L., and Mayer, J. M. (2012) J. Phys. Chem. B 116, 571-584
138. Rappaport, F. and Diner, B. A. (2008) Coord. Chem. Rev. 252, 259-272
139. Costentin, C. (2008) Chem. Rev. 108, 2145-2179
140. Costentin, C., Robert, M., and Savéant, J.-M. (2010) Chem. Rev. 110, PR1-PR40
141. Wardman, P. (1989) J. Phys. Chem. Ref. Data 18, 1637-1755
142. Song, N., Gagliardi, C. J., Binstead, R. A., Zhang, M.-T., Thorp, H., and Meyer, T. J. (2012) J. Am. Chem. Soc. 134, 18538-18541
143. Cheng, J.-P., Lu, Y., Zhu, X., and Mu, L. (1998) J. Org. Chem. 63, 6108-6114
144. Creutz, C. (1981) Inorg. Chem. 20, 4449-4452
145. Macartney, D. H. and Sutin, N. (1983) Inorg. Chim. Acta 74, 221-228
146. Warren, J. J. and Mayer, J. M. (2008) J. Am. Chem. Soc. 130, 7546-7547
147. Warren, J. J. and Mayer, J. M. (2008) J. Am. Chem. Soc. 130, 2774-2776
148. Warren, J. J. and Mayer, J. M. (2011) J. Am. Chem. Soc. 133, 8544-8551
149. Warren, J. J., Menzeleev, A. R., Kretchmer, J. S., Miller, T. F., Gray, H. B., and Mayer, J. M. (2013) J. Phys. Chem. Lett. 4, 519-523
150. Brigelius-Flohé, R. and Traber, M. G. (1999) FASEB J. 13, 1145-1155
151. Traber, M. G. and Atkinson, J. (2007) Free Radical Biol. Med. 43, 4-15
152. Burton, G. W. and Ingold, K. U. (1986) Acc. Chem. Res. 19, 194-201
153. Bisby, R. H. and Parker, A. W. (1995) Arch. Biochem. Biophys. 317, 170-178
154. Fitzpatrick, P. F. (1999) Annu. Rev. Biochem. 68, 355-381
155. Massey, V. (1994) J. Biol. Chem. 269, 22459-22462
156. Mayhew, S. G. (1999) Eur. J. Biochem. 265, 698-702
157. Anderson, R. F. (1983) Biochim. Biophys. Acta 722, 158-162
158. Toogood, H. S., Gardiner, J. M., and Scrutton, N. S. (2010) ChemCatChem 2, 892-914
159. Massey, V. (1994) J. Biol. Chem. 269, 22459-22462
160. Fitzpatrick, P. F. (1999) Annu. Rev. Biochem. 68, 355-381
161. Roth, J. P. and Klinman, J. P. (2003) Proc. Natl. Acad. Sci. U.S.A. 100, 62-67
162. Roth, J. P., Wincek, R., Nodet, G., Edmondson, D. E., McIntire, W. S., and Klinman, J. P. (2004) J. Am. Chem. Soc. 126, 15120-15131
163. Brinkley, D. W. and Roth, J. P. (2005) J. Am. Chem. Soc. 127, 15720-15721
164. (http://webbook.nist.gov/chemistry/).
165. Costentin, C., Robert, M., and Savéant, J.-M. (2013) Chem. Soc. Rev. 42, 2423-2436
166. Grice, K. A. and Kubiak, C. P. (2014) Adv. Inorg. Chem. 66, 163-188
167. Schrock, R. R. (2005) Acc. Chem. Res. 38, 955-962
168. Anderson, J. S., Rittle, J., and Peters, J. C. (2013) Nature 501, 84-87
169. Hoffman, B. M., Lukoyanov, D., Dean, D. R., and Seefeldt, L. C. (2013) Acc. Chem. Res. 46, 587-595
170. Collman, J. P., Boulatov, R., Sunderland, C. J., and Fu, L. (2004) Chem. Rev. 104, 561-588
171. Vasudevan, P., Santosh Mann, N., and Tyagi, S. (1990) Transition Met. Chem. 15, 81-90
172. Dogutan, D. K., Stoian, S. A., McGuire, R., Schwalbe, M., Teets, T. S., and Nocera, D. G. (2011) J. Am. Chem. Soc. 133, 131-140
173. Carver, C. T., Matson, B. D., and Mayer, J. M. (2012) J. Am. Chem. Soc. 134, 5444-5447
174. Matson, B. D., Carver, C. T., Von Ruden, A., Yang, J. Y., Raugei, S., and Mayer, J. M. (2012) Chem. Commun. 48, 11100-11102
175. Groves, J. T., Haushalter, R. C., Nakamura, M., Nemo, T. E., and Evans, B. J. (1981) J. Am. Chem. Soc. 103, 2884-2886
176. Groves, J. T. (2006) J. Inorg. Biochem. 100, 434-447
177. Rittle, J. and Green, M. T. (2010) Science 330, 933-937
178. Yosca, T. H., Rittle, J., Krest, C. M., Onderko, E. L., Silakov, A., Calixto, J. C., Behan, R. K., and Green, M. T. (2013) Science 342, 825-829
179. Guengerich, F. P. (2001) Chem. Res. Toxicol. 14, 611-650
180. Sono, M., Roach, M. P., Coulter, E. D., and Dawson, J. H. (1996) Chem. Rev. 96, 2841-2887
181. Kirby, J. P., van, D., Niels, A., Chang, C. K., and Nocera, D. G. (1995) Tetrahedron Lett. 36, 3477-3480
182. Young, E. R., Rosenthal, J., Hodgkiss, J. M., and Nocera, D. G. (2009) J. Am. Chem. Soc. 131, 7678-7684
183. Warren, J. J. and Mayer, J. M. (2008) J. Am. Chem. Soc. 130, 2774-2776
184. Warren, J. J. (2010) Concerted Proton-Electron Transfer Reactions of Small Molecule Iron-Porphyrin Complexes and Organic Substrates Relevant to Biological Processes. Ph.D. Dissertation, University of Washington, Seattle.
185. Reid, L. S., Mauk, M. R., and Mauk, A. G. (1984) J. Am. Chem. Soc. 106, 2182-2185
186. Costentin, C., Drouet, S., Robert, M., and Savéant, J.-M. (2012) Science 338, 90-94
187. McDonald, A. R. and Que, L., Jr. (2013) Coord. Chem. Rev. 257, 414-428
188. Collins, T. J. (2002) Acc. Chem. Res. 35, 782-790
189. Decker, A., Clay, M. D., and Solomon, E. I. (2006) J. Inorg. Biochem. 100, 697-706
190. Nam, W. (2007) Acc. Chem. Res. 40, 522-531
191. Jonas, R. T. and Stack, T. D. P. (1997) J. Am. Chem. Soc. 119, 8566-8567
192. Roth, J. P. and Mayer, J. M. (1999) Inorg. Chem. 38, 2760-2761
193. Roth, J. P., Lovell, S., and Mayer, J. M. (2000) J. Am. Chem. Soc. 122, 5486-5498
194. Yoder, J. C., Roth, J. P., Gussenhoven, E. M., Larsen, A. S., and Mayer, J. M. (2003) J. Am. Chem. Soc. 125, 2629-2640
195. Manner, V. W., Markle, T. F., Freudenthal, J. H., Roth, J. P., and Mayer, J. M. (2008) Chem. Commun. 256-258
196. Roth, J. P., Yoder, J. C., Won, T.-J., and Mayer, J. M. (2001) Science 294, 2524-2526
197. Mader, E. A., Larsen, A. S., and Mayer, J. M. (2004) J. Am. Chem. Soc. 126, 8066-8067
198. Warren, J. J., and Mayer, J. M. (2012) Application of the Marcus Cross Relation to Hydrogen Atom Transfer/Proton-Coupled Electron Transfer Reactions, In Proton-Coupled Electron Transfer: A Carrefour of Chemical Reactivity Traditions, Formosinho, S.; Barroso, M., Eds.; RSC Publishing: Cambridge; pp 1-31.
199. Mader, E. A., Davidson, E. R., and Mayer, J. M. (2007) J. Am. Chem. Soc. 129, 5153-5166
200. Mader, E. A., Manner, V. W., Markle, T. F., Wu, A., Franz, J. A., and Mayer, J. M. (2009) J. Am. Chem. Soc. 131, 4335-4345
201. Abu-Omar, M. M., Loaiza, A., and Hontzeas, N. (2005) Chem. Rev. 105, 2227-2252
202. Burger, R. M. (1998) Chem. Rev. 98, 1153-1170
203. Solomon, E. I., Decker, A., and Lehnert, N. (2003) Proc. Natl. Acad. Sci. U.S.A. 100, 3589-3594
204. Costas, M., Mehn, M. P., Jensen, M. P., and Que, L., Jr. (2004) Chem. Rev. 104, 939-986
205. de Oliveira, F. T., Chanda, A., Banerjee, D., Shan, X., Mondal, S., Que, L., Bominaar, E. L., Münck, E., and Collins, T. J. (2007) Science 315, 835-838
206. Park, J., Morimoto, Y., Lee, Y.-M., Nam, W., and Fukuzumi, S. (2014) Inorg. Chem. 53, 3618-3628
207. Wang, D., Ray, K., Collins, M. J., Farquhar, E. R., Frisch, J. R., Gomez, L., Jackson, T. A., Kerscher, M., Waleska, A., Comba, P., Costas, M., and Que, L. (2013) Chem. Sci. 4, 282-291
208. Que, L., Jr. (2007) Acc. Chem. Res. 40, 493-500
209. Venkateswara, R. P. and Holm, R. H. (2004) Chem. Rev. 104, 527-560
210. Gloaguen, F. and Rauchfuss, T. B. (2009) Chem. Soc. Rev. 38, 100-108
211. DuBois, D. L. and Bullock, R. M. (2011) Eur. J. Inorg. Chem. 2011, 1017-1027
212. Ginovska-Pangovska, B., Dutta, A., Reback, M. L., Linehan, J. C., and Shaw, W. J. (2014) Acc. Chem. Res. 47, 2621-2630
213. Helm, M. L., Stewart, M. P., Bullock, R. M., DuBois, M. R., and DuBois, D. L. (2011) Science 333, 863-866
214. Liu, T., DuBois, D. L., and Bullock, R. M. (2013) Nat. Chem. 5, 228-233
215. Chen, S., Ho, M.-H., Bullock, R. M., DuBois, D. L., Dupuis, M., Rousseau, R., and Raugei, S. (2014) ACS Catal. 4, 229-242
216. Wiese, S., Kilgore, U. J., Ho, M.-H., Raugei, S. R., DuBois, D. L., Bullock, R. M., and Helm, M. L. (2013) ACS Catal. 3, 2527-2535
217. Amélie Kochem, A., Neese, F., and van Gastel, M. (2014) J. Phys. Chem. C 118, 2350-2360
218. Solomon, E. I., Augustine, A. J., and Yoon, J. (2008) Dalton Trans. 3921-3932
219. Bento, I., Silva, C., Chen, Z., Martins, L., Lindley, P., and Soares, C. (2010) BMC Struct. Biol. 10, 28-42
220. Saouma, C. T., Kaminsky, W., and Mayer, J. M. (2012) J. Am. Chem. Soc. 134, 7293-7296
221. Saouma, C. T., Pinney, M. M., and Mayer, J. M. (2014) Inorg. Chem. 53, 3153-3161
222. Ballmann, J., Albers, A., Demeshko, S., Dechert, S., Bill, E., Bothe, E., Ryde, U., and Meyer, F. (2008) Angew. Chem., Int. Ed. 47, 9537-9541
223. Albers, A., Bayer, T., Demeshko, S., Dechert, S., and Meyer, F. (2013) Chem.-Eur. J. 19, 10101-10106
224. Albers, A., Demeshko, S., Dechert, S., Saouma, C. T., Mayer, J. M., and Meyer, F. (2014) J. Am. Chem. Soc. 136, 3946-3954
225. Zu, Y., Fee, J. A., and Hirst, J. (2001) J. Am. Chem. Soc. 123, 9906-9907
226. Zu, Y., Couture, M. M.-J., Kolling, D. R. J., Crofts, A. R., Eltis, L. D., Fee, J. A., and Hirst, J. (2003) Biochemistry 42, 12400-12408
227. Umena, Y., Kawakami, K., Shen, J.-R., and Kamiya, N. (2011) Nature 473, 55-60
228. Kern, J., Alonso-Mori, R., Tran, R., Hattne, J., Gildea, R. J., Echols, N., Glöckner, C., Hellmich, J., Laksmono, H., Sierra, R. G., Lassalle-Kaiser, B., Koroidov, S., Lampe, A., Han, G., Gul, S., DiFiore, D., Milathianaki, D., Fry, A. R., Miahnahri, A., Schafer, D. W., Messerschmidt, M., Seibert, M. M., Koglin, J. E., Sokaras, D., Weng, T.-C., Sellberg, J., Latimer, M. J., Grosse-Kunstleve, R. W., Zwart, P. H., White, W. E., Glatzel, P., Adams, P. D., Bogan, M. J., Williams, G. J., Boutet, S., Messinger, J., Zouni, A., Sauter, N. K., Yachandra, V. K., Bergmann, U., and Yano, J. (2013) Science 340, 491-495
229. Pokhrel, R. and Brudvig, G. W. (2014) Phys. Chem. Chem. Phys. 16, 11812-11821
230. Tsui, E. Y., Tran, R., Yano, J., and Agapie, T. (2013) Nat. Chem. 5, 293-299
231. March, J. (1985) Advanced Organic Chemistry, 3rd ed., Wiley-Interscience, New York.
232. Gardner, K. A., Kuehnert, L. L., and Mayer, J. M. (1997) Inorg. Chem. 36, 2069-2078
233. Yocum, C. F., Blankenship, R. E., and Ferguson-Miller, S. (2005) Adv. Photosynth. Respir. 22, 1-10
234. Batinic-Haberle, I., Reboucas, J. S., and Spasojevic, I. (2010) Antioxid. Redox Signaling 13, 877-918
235. Halliwell, B. and Gutteridge, J. M. C. (2007) Free radicals in biology and medicine, Oxford University Press, Oxford, U.K.
236. Riley, D. P., Lennon, P. J., Neumann, W. L., and Weiss, R. H. (1997) J. Am. Chem. Soc. 119, 6522-6528
237. Yikilmaz, E., Porta, J., Grove, L. E., Vahedi-Faridi, A., Bronshteyn, Y., Brunold, T. C., Borgstahl, G. E. O., and Miller, A.-F. (2007) J. Am. Chem. Soc. 129, 9927-9940
238. Grove, L. E. and Brunold, T. C. (2008) Comments Inorg. Chem. 29, 134-168
239. Cramer, C. J. and Tolman, W. B. (2007) Acc. Chem. Res. 40, 601-608
240. Kim, E., Chufán, E. E., Kamaraj, K., and Karlin, K. D. (2004) Chem. Rev. 104, 1077-1134
241. Liang, H.-C., Dahan, M., and Karlin, K. D. (1999) Curr. Opin. Chem. Biol. 3, 168-175
242. Lyons, C. T. and Stack, T. D. P. (2013) Coord. Chem. Rev. 257, 528-540
243. Waidmann, C. R., Zhou, X., Tsai, E. A., Kaminsky, W., Hrovat, D. A., Borden, W. T., and Mayer, J. M. (2009) J. Am. Chem. Soc. 131, 4729-4743
244. Bakac, A. (2000) J. Am. Chem. Soc. 122, 1092-1097
245. Gray, H. B. and Winkler, J. R. (2003) Q. Rev. Biophys. 36, 341-372
246. Kuss-Petermann, M., Wolf, H., Stalke, D., and Wenger, O. S. (2012) J. Am. Chem. Soc. 134, 12844-12854
247. Kuss-Petermann, M. and Wenger, O. S. (2013) J. Phys. Chem. A 117, 5726-5733
248. Chen, J., Kuss-Petermann, M., and Wenger, O. S. (2014) Chem.-Eur. J. 20, 4098-4104
249. Wenger, O. S. (2011) Chem. Soc. Rev. 40, 3538-3550
250. Warren, J. J., Menzeleev, A. R., Kretchmer, J. S., Miller, T. F., Gray, H. B., and Mayer, J. M. (2013) J. Phys. Chem. Lett. 4, 519-523
251. Manner, V. W., Dipasquale, A. G., and Mayer, J. M. (2008) J. Am. Chem. Soc. 130, 7210-7211
252. Manner, V. W. and Mayer, J. M. (2009) J. Am. Chem. Soc. 131, 9874-9875
253. DuBois, D. L. and Bullock, R. M. (2011) Eur. J. Inorg. Chem. 2011, 1017-1027
254. Costentin, C., Robert, M., Savéant, J.-M., and Tard, C. (2014) Acc. Chem. Res. 47, 271-280
255. Pagba, C. V. and Barry, B. A. (2012) J. Phys. Chem. B 116, 10590-10599
256. Sibert, R. S., Josowicz, M., and Barry, B. A. (2010) ACS Chem. Biol. 5, 1157-1168
257. Sibert, R., Josowicz, M., Porcelli, F., Veglia, G., Range, K., and Barry, B. A. (2007) J. Am. Chem. Soc. 129, 4393-4400
258. Berry, B. W., Martínez-Rivera, M. C., and Tommos, C. (2012) Proc. Natl. Acad. Sci. U.S.A. 109, 9739-9743
259. Martínez-Rivera, M. C., Berry, B. W., Valentine, K. G., Westerlund, K., Hay, S., and Tommos, C. (2011) J. Am. Chem. Soc. 133, 17786-17795
260. Ginovska-Pangovska, B., Dutta, A., Reback, M. L., Linehan, J. C., and Shaw, W. J. (2014) Acc. Chem. Res. 47, 2621-2630
261. Green, M. T., Dawson, J. H., and Gray, H. B. (2004) Science 304, 1653-1656
262. Esselborn, J., Lambertz, C., Adamska-Venkatesh, A., Simmons, T., Berggren, G., Noth, J., Siebel, J., Hemschemeier, A., Artero, V., Reijerse, E., Fontecave, M., Lubitz, W., and Happe, T. (2013) Nat. Chem. Biol. 9, 607-609
263. Layfield, J. P. and Hammes-Schiffer, S. (2014) Chem. Rev. 114, 3466-3494