Detection and kinetic characterization of a highly reactive heme-thiolate peroxygenase compound i

Journal of the American Chemical Society

Volumn 134, Issue 31, 2012, Pages 12897-12900

  Wang, Xiaoshi ^a   Peter, Sebastian ^b   Kinne, Matthias ^b   Hofrichter, Martin ^b   Groves, John T ^a  

^a PRINCETON UNIVERSITY   (United States)

^b International Graduate School Zittau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE OXYGEN SPECIES; BOND DISSOCIATION ENTHALPIES; C-H BOND; COMPOUND I; CYTOCHROME P450; DECOMPOSITION RATE; EXTRACELLULAR; KINETIC CHARACTERIZATION; ORDERS OF MAGNITUDE; OXOIRON; RADICAL CATIONS; SECOND-ORDER RATE CONSTANTS; SPECTRAL FEATURE; SYMMETRICAL TRANSITION; TERMINAL OXIDANTS; TRANSITION STATE;

CHEMICAL BONDS; HYDROGEN PEROXIDE; HYDROXYLATION; IONIZATION OF GASES; PARAFFINS; PORPHYRINS; REACTION KINETICS;

RATE CONSTANTS;

ALKANE DERIVATIVE; CHLORIDE PEROXIDASE; CHLOROPEROXIDASE I; CYTOCHROME P450; HEME THIOLATE PEROXYGENASE COMPOUND I; HEME THIOLATE PEROXYGENASE COMPOUND II; HYDROGEN PEROXIDE; OXIDIZING AGENT; OXYGENASE; PORPHYRIN DERIVATIVE; RADICAL; REACTIVE OXYGEN METABOLITE; TERT BUTOXY RADICAL; UNCLASSIFIED DRUG;

AGROCYBE AEGERITA; ARTICLE; DECOMPOSITION; DISSOCIATION; ENTHALPY; ENTROPY; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME SUBSTRATE; HYDROGEN BOND; HYDROXYLATION; PH; REACTION ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

AGROCYBE; CHLOROBENZOATES; FERRIC COMPOUNDS; HYDROXYLATION; KINETICS; MIXED FUNCTION OXYGENASES;

EID: 84864668830     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3049223     Document Type: Article

References (38)

1. Hofrichter, M.; Ullrich, R.; Pecyna, M. J.; Liers, C.; Lundell, T. Appl. Microbiol. Biotechnol. 2010, 87, 871
2. Kinne, M.; Poraj-Kobielska, M.; Ralph, S. A.; Ullrich, R.; Hofrichter, M.; Hammel, K. E. J. Biol. Chem. 2009, 284, 29343
3. Peter, S.; Kinne, M.; Wang, X.; Ullrich, R.; Kayser, G.; Groves, J. T.; Hofrichter, M. FEBS J. 2011, 278, 3667
4. Poraj-Kobielska, M.; Kinne, M.; Ullrich, R.; Scheibner, K.; Kayser, G.; Hammel, K. E.; Hofrichter, M. Biochem. Pharmacol. 2011, 82, 789
5. Pecyna, M. J.; Ullrich, R.; Bittner, B.; Clemens, A.; Scheibner, K.; Schubert, R.; Hofrichter, M. Appl. Microbiol. Biotechnol. 2009, 84, 885
6. Piontek, K.; Ullrich, R.; Liers, C.; Diederichs, K.; Plattner, D. A.; Hofrichter, M. Acta Crystallogr., Sect. F 2010, 66, 693
7. Kinne, M., PhD Thesis, International Graduate School, Zittau, Germany, 2010, p 71.
8. Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A. M.; Maves, S. A.; Benson, D. E.; Sweet, B. M.; Ringe, D.; Petsko, G. A.; Sligar, S. G. Science 2000, 287, 1615
9. Sundaramoorthy, M.; Terner, J.; Poulos, T. L. Structure 1995, 3, 1367
10. Sundaramoorthy, M.; Terner, J.; Poulos, T. L. Chem. Biol. 1998, 5, 461
11. Lee, D. S.; Yamada, A.; Sugimoto, H.; Matsunaga, I.; Ogura, H.; Ichihara, K.; Adachi, S.; Park, S. Y.; Shiro, Y. J. Biol. Chem. 2003, 278, 9761
12. Shoji, O.; Fujishiro, T.; Nakajima, H.; Kim, M.; Nagano, S.; Shiro, Y.; Watanabe, Y. Angew. Chem., Int. Ed. 2007, 46, 3656
13. Fang, Z.; Breslow, R. Bioorg. Med. Chem. Lett. 2005, 15, 5463
14. Rittle, J.; Green, M. T. Science 2010, 330, 933
15. Rittle, J.; Younker, J. M.; Green, M. T. Inorg. Chem. 2010, 49, 3610
16. Bell, S. R.; Groves, J. T. J. Am. Chem. Soc. 2009, 131, 9640
17. Isin, E. M.; Guengerich, F. P. Anal. Bioanal. Chem. 2008, 392, 1019
18. Egawa, T.; Shimada, H.; Ishimura, Y. Biochem. Biophys. Res. Commun. 1994, 201, 1464
19. Kellner, D. G.; Hung, S. C.; Weiss, K. E.; Sligar, S. G. J. Biol. Chem. 2002, 277, 9641
20. Spolitak, T.; Dawson, J. H.; Ballou, D. P. J. Biol. Chem. 2005, 280, 20300
21. Egawa, T.; Proshlyakov, D. A.; Miki, H.; Makino, R.; Ogura, T.; Kitagawa, T.; Ishimura, Y. J. Biol. Inorg. Chem. 2001, 6, 46
22. Palcic, M. M.; Rutter, R.; Araiso, T.; Hager, L. P.; Dunford, H. B. Biochem. Biophys. Res. Commun. 1980, 94, 1123
23. Fujishiro, T.; Shoji, O.; Nagano, S.; Sugimoto, H.; Shiro, Y.; Watanabe, Y. J. Biol. Chem. 2011, 286, 29941
24. Araiso, T.; Rutter, R.; Palcic, M. M.; Hager, L. P.; Dunford, H. B. Can. J. Biochem. 1981, 59, 233
25. Kluge, M.; Ullrich, R.; Scheibner, K.; Hofrichter, M. Green Chem. 2012, 14, 440
26. Zaks, A.; Dodds, D. R. J. Am. Chem. Soc. 1995, 117, 10419
27. Zhang, R.; Nagraj, N.; Lansakara, D. S. P.; Hager, L. P.; Newcomb, M. Org. Lett. 2006, 8, 2731
28. Lai, W.; Li, C.; Chen, H.; Shaik, S. Angew. Chem., Int. Ed. 2012, 51, 5556
29. Shaik, S.; Cohen, S.; Wang, Y.; Chen, H.; Kumar, D.; Thiel, W. Chem. Rev. 2010, 110, 949
30. Klinker, E. J.; Shaik, S.; Hirao, H.; Que, L., Jr. Angew. Chem., Int. Ed. 2009, 48, 1291
31. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441
32. Finn, M.; Friedline, R.; Suleman, N. K.; Wohl, C. J.; Tanko, J. M. J. Am. Chem. Soc. 2004, 126, 7578
33. Green, M. T.; Dawson, J. H.; Gray, H. B. Science 2004, 304, 1653
34. Shaik, S.; Kumar, D.; de Visser, S. P. J. Am. Chem. Soc. 2008, 130, 14016
35. Shaik, S.; Lai, W. Z.; Chen, H.; Wang, Y. Acc. Chem. Res. 2010, 43, 1154
36. Liu, W.; Groves, J. T. J. Am. Chem. Soc. 2010, 132, 12847
37. Chen, K.; Eschenmoser, A.; Baran, P. S. Angew. Chem., Int. Ed. 2009, 48, 9705
38. Tanko, J. M.; Friedline, R.; Suleman, N. K.; Castagnoli, N. J. Am. Chem. Soc. 2001, 123, 5808