Nitrogen Oxide Atom-Transfer Redox Chemistry; Mechanism of NO(g) to Nitrite Conversion Utilizing μ-oxo Heme-FeIII-O-CuII(L) Constructs

Journal of the American Chemical Society

Volumn 137, Issue 20, 2015, Pages 6602-6615

  Hematian, Shabnam ^a   Kenkel, Isabell ^b   Shubina, Tatyana E ^b   Dürr, Maximilian ^b   Liu, Jeffrey J ^a   Siegler, Maxime A ^a   Ivanovic Burmazovic, Ivana ^b   Karlin, Kenneth D ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATION REACTIONS; ELECTRON SPIN RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MIXTURES; NITRIC OXIDE; NITROGEN OXIDES; REACTION INTERMEDIATES; TEMPERATURE;

CHEMICAL EQUATIONS; CYTOCHROME C OXIDASE; INTERMEDIATE SPECIE; KINETIC INVESTIGATIONS; KINETIC THERMODYNAMIC PARAMETERS; OXIDATIVE CONVERSION; SEQUENTIAL ADDITION; STOPPED-FLOW MEASUREMENTS;

PORPHYRINS;

ALIPHATIC AMINE; CUPRIC ION; FERRIC ION; HEME; NITRIC OXIDE; NITRITE; NITROGEN OXIDE; PYRIDINE DERIVATIVE; COPPER; ORGANOMETALLIC COMPOUND; OXYGEN;

ARTICLE; ATOM; CHEMICAL REACTION; COOLING; CRYOSPRAY IONIZATION MASS SPECTROMETRY; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTRON SPIN RESONANCE; KINETICS; LOW TEMPERATURE; MASS SPECTROMETRY; OXIDATION REDUCTION REACTION; THERMODYNAMICS; CHEMISTRY; CONFORMATION; MOLECULAR MODEL; SYNTHESIS;

COPPER; FERRIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITRITES; NITROGEN OXIDES; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN;

EID: 84930221966     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02174     Document Type: Article

References (78)

1. Ignarro, L. J. Nitric Oxide as a Communication Signal in Vascular and Neuronal Cells. In Nitric Oxide: Principles and Actions; Lancaster, J., Ed.; Academic Press, Inc.: New York, 1996; pp 111.
2. Pfeiffer, S.; Mayer, B.; Hemmens, B. Angew. Chem., Int. Ed. 1999, 38, 1715 - 1731
3. Nitric Oxide, Biology and Pathobiology; Ignarro, L. J., Ed.; Academic Press: San Diego, 2000.
4. Miranda, K. M.; Espey, M. G.; Jourd'heuil, D.; Grisham, M. B.; Fukuto, J. M.; Feelisch, M.; Wink, D. A. Nitric Oxide 2000, 41 - 55
5. Feelisch, M.; Olson, K. R. Nitric Oxide 2013, 35, 2 - 4
6. Lehnert, N.; Berto, T. C.; Galinato, M. G. I.; Goodrich, L. E. The Role of Heme-Nitrosyls in the Biosynthesis, Transport, Sensing, and Detoxification of Nitric Oxide (NO) in Biological Systems: Enzymes and Model Complexes. In The Handbook of Porphyrin Science; Kadish, K. M.; Smith, K.; Guilard, R., Eds.; World Scientific: Singapore, 2011; Vol. 14; pp 1 - 247.
7. Maia, L. B.; Moura, J. J. G. Chem. Rev. 2014, 114, 5273 - 5357
8. Marletta, M. A. J. Biol. Chem. 1993, 268, 12231 - 12234
9. Stuehr, D. J. Biochim. Biophys. Acta 1999, 1411, 217 - 230
10. Alderton, W. K.; Cooper, C. E.; Knowles, R. G. Biochem. J. 2001, 357, 593 - 615
11. Zhu, Y.; Silverman, R. B. Biochemistry 2008, 47, 2231 - 2243
12. Crane, B. R. Biochem. Soc. Trans. 2008, 036, 1149 - 1154
13. Dezfulian, C.; Raat, N.; Shiva, S.; Gladwin, M. T. Cardiovasc. Res. 2007, 75, 327 - 338
14. Samouilov, A.; Kuppusamy, P.; Zweier, J. L. Arch. Biochem. Biophys. 1998, 357, 1 - 7
15. Gladwin, M. T.; Grubina, R.; Doyle, M. P. Acc. Chem. Res. 2009, 42, 157 - 167
16. van Faassen, E. E.; Bahrami, S.; Feelisch, M.; Hogg, N.; Kelm, M.; Kim-Shapiro, D. B.; Kozlov, A. V.; Li, H.; Lundberg, J. O.; Mason, R.; Nohl, H.; Rassaf, T.; Samouilov, A.; Slama-Schwok, A.; Shiva, S.; Vanin, A. F.; Weitzberg, E.; Zweier, J.; Gladwin, M. T. Med. Res. Rev. 2009, 29, 683 - 741
17. Kim-Shapiro, D. B.; Gladwin, M. T. Nitric Oxide 2014, 38, 58 - 68
18. Castello, P. R.; David, P. S.; McClure, T.; Crook, Z.; Poyton, R. O. Cell Metab. 2006, 3, 277 - 287
19. Feelisch, M.; Fernandez, B. O.; Bryan, N. S.; Garcia-Saura, M. F.; Bauer, S.; Whitlock, D. R.; Ford, P. C.; Janero, D. R.; Rodriguez, J.; Ashrafian, H. J. Biol. Chem. 2008, 283, 33927 - 33934
20. Poyton, R. O.; Castello, P. R.; Ball, K. A.; Woo, D. K.; Pan, N. Ann. N.Y. Acad. Sci. 2009, 1177, 48 - 56
21. Gupta, K. J.; Igamberdiev, A. U. Mitochondrion 2011, 11, 537 - 543
22. Kim, E.; Chufán, E. E.; Kamaraj, K.; Karlin, K. D. Chem. Rev. 2004, 104, 1077 - 1133
23. Yoshikawa, S.; Shinzawa-Itoh, K.; Nakashima, R.; Yaono, R.; Yamashita, E.; Inoue, N.; Yao, M.; Jei-Fei, M.; Libeu, C. P.; Mizushima, T.; Yamaguchi, H.; Tomizaki, T.; Tsukihara, T. Science 1998, 280, 1723 - 1729
24. Torres, J.; Cooper, C. E.; Wilson, M. T. J. Biol. Chem. 1998, 273, 8756 - 8766
25. Sarti, P.; Giuffre, A.; Barone, M. C.; Forte, E.; Mastronicola, D.; Brunori, M. Free Radic. Biol. Med. 2003, 34, 509 - 520
26. Mason, M. G.; Nicholls, P.; Wilson, M. T.; Cooper, C. E. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 708 - 713
27. Sarti, P.; Forte, E.; Mastronicola, D.; Giuffrè, A.; Arese, M. Biochim. Biophys. Acta 2012, 1817, 610 - 619
28. Castello, P. R.; Woo, D. K.; Ball, K.; Wojcik, J.; Liu, L.; Poyton, R. O. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 8203 - 8208
29. Benamar, A.; Rolletschek, H.; Borisjuk, L.; Avelange-Macherel, M.-H.; Curien, G.; Mostefai, H. A.; Andriantsitohaina, R.; Macherel, D. Biochim. Biophys. Acta 2008, 1777, 1268 - 1275
30. Gladwin, M. T.; Shiva, S. Circ. Res. 2009, 104, 1136 - 1138
31. Nicholls, P.; Sharpe, M.; Torres, J.; Wilson, M. T.; Cooper, C. E. Biochem. Soc. Trans. 1998, 26, S323
32. Torres, J.; Sharpe, M. A.; Rosquist, A.; Cooper, C. E.; Wilson, M. T. FEBS Lett. 2000, 475, 263 - 266
33. Igamberdiev, A. U.; Ratcliffe, R. G.; Gupta, K. J. Mitochondrion 2014, 19, 329 - 333
34. Hematian, S.; Siegler, M. A.; Karlin, K. D. J. Am. Chem. Soc. 2012, 134, 18912 - 18915
35. Hematian, S.; Siegler, M. A.; Karlin, K. D. J. Biol. Inorg. Chem. 2014, 19, 515 - 528
36. Fox, S.; Nanthakumar, A.; Wikström, M.; Karlin, K. D.; Blackburn, N. J. J. Am. Chem. Soc. 1996, 118, 24 - 34
37. Kopf, M.-A.; Neuhold, Y.-M.; Zuberbühler, A. D.; Karlin, K. D. Inorg. Chem. 1999, 38, 3093 - 3102
38. Karlin, K. D.; Nanthakumar, A.; Fox, S.; Murthy, N. N.; Ravi, N.; Huynh, B. H.; Orosz, R. D.; Day, E. P. J. Am. Chem. Soc. 1994, 116, 4753 - 4763
39. Nanthakumar, A.; Fox, S.; Murthy, N. N.; Karlin, K. D.; Ravi, N.; Huynh, B. H.; Orosz, R. D.; Day, E. P.; Hagen, K. S.; Blackburn, N. J. J. Am. Chem. Soc. 1993, 115, 8513 - 8514
40. Halime, Z.; Kieber-Emmons, M. T.; Qayyum, M. F.; Mondal, B.; Gandhi, T.; Puiu, S. C.; Chufán, E. E.; Sarjeant, A. A. N.; Hodgson, K. O.; Hedman, B.; Solomon, E. I.; Karlin, K. D. Inorg. Chem. 2010, 49, 3629 - 3645
41. Kim, E.; Helton, M. E.; Wasser, I. M.; Karlin, K. D.; Lu, S.; Huang, H.-w.; Moënne-Loccoz, P.; Incarvito, C. D.; Rheingold, A. L.; Honecker, M.; Kaderli, S.; Zuberbühler, A. D. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 3623 - 3628
42. Lee, S. C.; Holm, R. H. J. Am. Chem. Soc. 1993, 115, 5833 - 5834
43. Ju, T. D.; Ghiladi, R. A.; Lee, D.-H.; van Strijdonck, G. P. F.; Woods, A. S.; Cotter, R. J.; Young, V. G., J.; Karlin, K. D. Inorg. Chem. 1999, 38, 2244 - 2245
44. Chishiro, T.; Shimazaki, Y.; Tani, F.; Naruta, Y. Chem. Comm 2005, 1079 - 1081
45. +, which is described later in the text in detail.
46. 2)] (Figure S7). However, a detailed examination of the spectra revealed differences in relative extinction coefficients of the Soret and Q-bands.
47. Yoshimura, T. Bull. Chem. Soc. Jpn. 1991, 64, 2819 - 2828
48. Morse, R. H.; Chan, S. I. J. Biol. Chem. 1980, 255, 7876 - 7882
49. Cheng, L.; Richter-Addo, G. B. Binding and Activation of Nitric Oxide by Metalloporphyrins and Heme. In Porphyrin Handbook; Kadish, K. M.; Simith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 4, Chapter 33, pp 219 - 291.
50. Lymar, S. V.; Schwarz, H. A.; Czapski, G. J. Phys. Chem. A 2002, 106, 7245 - 7250
51. Yamamoto, Y.; Moribe, S.; Ikoma, T.; Akiyama, K.; Zhang, Q.; Saito, F.; Tero-Kubota, S. Mol. Phys. 2006, 104, 1733 - 1737
52. Kudrik, E. V.; Makarov, S. V.; Zahl, A.; van Eldik, R. Inorg. Chem. 2003, 42, 618 - 624
53. 2 moiety that is larger than the O-atom) results in the interaction with fewer solvent molecules. This causes the release of a number of solvent molecules from the solvation sphere escaping to the bulk, which leads to the positive entropy change, the value of which is dependent on solvent polarity.
54. -1 at -74°C.
55. Wanat, A.; Schneppensieper, T.; Stochel, G.; van Eldik, R.; Bill, E.; Wieghardt, K. Inorg. Chem. 2002, 41, 4 - 10
56. Schneppensieper, T.; Wanat, A.; Stochel, G.; van Eldik, R. Inorg. Chem. 2002, 41, 2565 - 2573
57. off via extrapolation of the kinetic data obtained in the stopped-flow experiments.
58. Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements; Pergamon Press: Oxford, 1993.
59. Heinecke, J.; Ford, P. C. Coord. Chem. Rev. 2010, 254, 235 - 247
60. Ellison, M. K.; Schulz, C. E.; Scheidt, W. R. Inorg. Chem. 1999, 38, 100 - 108
61. Scheidt, W. R.; Frisse, M. E. J. Am. Chem. Soc. 1975, 97, 17 - 21
62. Shubina, T. E. Adv. Inorg. Chem. 2010, 62, 261 - 299
63. Loullis, A.; Noor, M. R.; Soulimane, T.; Pinakoulaki, E. Chem. Comm 2015, 51, 286 - 289
64. Hoshino, M.; Maeda, M.; Konishi, R.; Seki, H.; Ford, P. C. J. Am. Chem. Soc. 1996, 118, 5702 - 5707
65. Ford, P. C.; Fernandez, B. O.; Lim, M. D. Chem. Rev. 2005, 105, 2439 - 2455
66. Fernandez, B. O.; Lorkovic, I. M.; Ford, P. C. Inorg. Chem. 2003, 42, 2 - 4
67. Ford, P. C. Inorg. Chem. 2010, 49, 6226 - 6239
68. Sharma, V.; Karlin, K. D.; Wikström, M. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 16844 - 16849
69. Ford, P. C.; Lorkovic, I. M. Chem. Rev. 2002, 102, 993 - 1017
70. Wang, J.; Schopfer, M. P.; Sarjeant, A. A. N.; Karlin, K. D. J. Am. Chem. Soc. 2009, 131, 450 - 451
71. Schopfer, M. P.; Mondal, B.; Lee, D.-H.; Sarjeant, A. A. N.; Karlin, K. D. J. Am. Chem. Soc. 2009, 131, 11304 - 11305
72. Ghiladi, R. A.; Kretzer, R. M.; Guzei, I.; Rheingold, A. L.; Neuhold, Y.-M.; Hatwell, K. R.; Zuberbühler, A. D.; Karlin, K. D. Inorg. Chem. 2001, 40, 5754 - 5767
73. Lucas, H. R.; Meyer, G. J.; Karlin, K. D. J. Am. Chem. Soc. 2010, 132, 12927 - 12940
74. Liang, H.-C.; Zhang, C. X.; Henson, M. J.; Sommer, R. D.; Hatwell, K. R.; Kaderli, S.; Zuberbuehler, A. D.; Rheingold, A. L.; Solomon, E. I.; Karlin, K. D. J. Am. Chem. Soc. 2002, 124, 4170 - 4171
75. Wang, J.; Schopfer, M. P.; Puiu, S. C.; Sarjeant, A. A. N.; Karlin, K. D. Inorg. Chem. 2010, 49, 1404 - 1419
76. Lorkovic, I.; Ford, P. C. J. Am. Chem. Soc. 2000, 122, 6516 - 6517
77. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112 - 122
78. Jee, J. E.; Eigler, S.; Hampel, F.; Jux, N.; Wolak, M.; Zahl, A.; Stochel, G.; van Eldik, R. Inorg. Chem. 2005, 44, 7717 - 7731