Are free radicals involved in IspH catalysis? An EPR and crystallographic investigation

Journal of the American Chemical Society

Volumn 134, Issue 27, 2012, Pages 11225-11234

  Wang, Weixue ^a   Wang, Ke ^a   Span, Ingrid ^b   Jauch, Johann ^c   Bacher, Adelbert ^b   Groll, Michael ^b   Oldfield, Eric ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPLEXES; DEHYDROXYLATIONS; DRUG TARGETS; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; EPR SPECTROSCOPY; HIGH POTENTIAL; IRON-SULFUR CLUSTERS; IRON-SULFUR PROTEINS; ISOPRENOID BIOSYNTHESIS; ISOTOPIC LABELING; MECHANISM OF ACTION; OH GROUP; PARAMAGNETIC INTERMEDIATES; REACTION MECHANISM; THIOREDOXIN REDUCTASE; TWO-ELECTRON REDUCTION;

BIOCHEMISTRY; CATALYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; IRON COMPOUNDS; PARAMAGNETIC RESONANCE; PARAMAGNETISM; REACTION INTERMEDIATES; SULFUR; X RAY CRYSTALLOGRAPHY;

FREE RADICALS;

BACTERIAL PROTEIN; FERRAOXETANE; FERREDOXIN; FREE RADICAL; IRON SULFUR PROTEIN; ISPH PROTEIN; OXETANE DERIVATIVE; THIOREDOXIN REDUCTASE; UNCLASSIFIED DRUG;

AQUIFEX AEOLICUS; ARTICLE; BIRCH REDUCTION; CATALYSIS; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; HYDROXYLATION; ISOTOPE LABELING; MAGNETISM; NONHUMAN; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ELECTRON SPIN RESONANCE SPECTROSCOPY; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; FREE RADICALS; MODELS, MOLECULAR; MUTATION; OXIDOREDUCTASES;

EID: 84863814421     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja303445z     Document Type: Article

References (47)

1. Eisenreich, W.; Bacher, A.; Arigoni, D.; Rohdich, F. Cell. Mol. Life Sci. 2004, 61, 1401
2. Wolff, M; Seemann, M.; Tse Sum Bui, B.; Frapart, Y.; Tritsch, D.; Garcia Estrabot, A.; Rodriguez-Concepcion, M.; Boronat, A.; Marquet, A.; Rohmer, M. FEBS Lett. 2003, 541, 115
3. Xiao, Y.; Chu, L.; Sanakis, Y.; Liu, P. J. Am. Chem. Soc. 2009, 131, 9931
4. Seemann, M.; Janthawornpong, K.; Schweizer, J.; Bottger, L. H.; Janoschka, A.; Ahrens-Botzong, A.; Tambou, E. N.; Rotthaus, O.; Trautwein, A. X.; Rohmer, M.; Schunemann, V. J. Am. Chem. Soc. 2009, 131, 13184
5. Grawert, T.; Span, I.; Eisenreich, W.; Rohdich, F.; Eppinger, J.; Bacher, A.; Groll, M. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 1077
6. Altincicek, B.; Duin, E. C.; Reichenberg, A.; Hedderich, R.; Kollas, A. K.; Hintz, M.; Wagner, S.; Wiesner, J.; Beck, E.; Jomaa, H. FEBS Lett. 2002, 532, 437
7. Rohdich, F.; Zepeck, F.; Adam, P.; Hecht, S.; Kaiser, J.; Laupitz, R.; Grawert, T.; Amslinger, S.; Eisenreich, W.; Bacher, A.; Arigoni, D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 1586
8. Van Hoof, S.; Lacey, C. J.; Rohrich, R. C.; Wiesner, J.; Jomaa, H.; Van Calenbergh, S. J. Org. Chem. 2008, 73, 1365
9. Wang, W.; Wang, K.; Liu, Y.-L.; No, J. H.; Nilges, M. J.; Oldfield, E. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 4522
10. Wang, K.; Wang, W.; No, J. H.; Zhang, Y.; Zhang, Y.; Oldfield, E. J. Am. Chem. Soc. 2010, 132, 6719
11. Wang, W.; Li, J.; Wang, K.; Smirnova, T. I.; Oldfield, E. J. Am. Chem. Soc. 2011, 133, 6525
12. Ahrens-Botzong, A.; Janthawornpong, K.; Wolny, J. A.; Tambou, E. N.; Rohmer, M.; Krasutsky, S.; Poulter, C. D.; Schunemann, V.; Seemann, M. Angew. Chem., Int. Ed. 2011, 50, 11976
13. Xiao, Y.; Zhao, Z. K.; Liu, P. J. Am. Chem. Soc. 2008, 130, 2164
14. Grawert, T.; Rohdich, F.; Span, I.; Bacher, A.; Eisenreich, W.; Eppinger, J.; Groll, M. Angew. Chem., Int. Ed. 2009, 48, 5756
15. Rekittke, I.; Wiesner, J.; Rohrich, R.; Demmer, U.; Warkentin, E.; Xu, W.; Troschke, K.; Hintz, M.; No, J. H.; Duin, E. C.; Oldfield, E.; Jomaa, H.; Ermler, U. J. Am. Chem. Soc. 2008, 130, 17206
16. Xiao, Y.; Chang, W. C.; Liu, H. W.; Liu, P. Org. Lett. 2011, 13, 5912
17. Chang, W. C.; Xiao, Y.; Liu, H. W.; Liu, P. Angew. Chem., Int. Ed. 2011, 50, 12304
18. Citron, C. A.; Brock, N. L.; Rabe, P.; Dickschat, J. S. Angew. Chem., Int. Ed. 2012, 51, 4053
19. Lee, H. I.; Sorlie, M.; Christiansen, J.; Yang, T. C.; Shao, J.; Dean, D. R.; Hales, B. J.; Hoffman, B. M. J. Am. Chem. Soc. 2005, 127, 15880
20. Lee, H. I.; Igarashi, R. Y.; Laryukhin, M.; Doan, P. E.; Dos Santos, P. C.; Dean, D. R.; Seefeldt, L. C.; Hoffman, B. M. J. Am. Chem. Soc. 2004, 126, 9563
21. Kennedy, M. C.; Werst, M.; Telser, J.; Emptage, M. H.; Beinert, H.; Hoffman, B. M. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8854
22. Werst, M. M.; Kennedy, M. C.; Beinert, H.; Hoffman, B. M. Biochemistry 1990, 29, 10526
23. Telser, J.; Emptage, M. H.; Merkle, H.; Kennedy, M. C.; Beinert, H.; Hoffman, B. M. J. Biol. Chem. 1986, 261, 4840
24. Span, I.; Grawert, T.; Bacher, A.; Eisenreich, W.; Groll, M. J. Mol. Biol. 2011, 416, 1
25. Belinskii, M. Chem. Phys. 1993, 172, 189
26. Mcmanus, H. J.; Fessenden, R. W.; Chipman, D. M. J. Phys. Chem. 1988, 92, 3778
27. Adedeji, D.; Hernandez, H.; Wiesner, J.; Kohler, U.; Jomaa, H.; Duin, E. C. FEBS Lett. 2007, 581, 279
28. Xu, W.; Lees, N. S.; Adedeji, D.; Wiesner, J.; Jomaa, H.; Hoffman, B. M.; Duin, E. C. J. Am. Chem. Soc. 2010, 132, 14509
29. Staples, C. R.; Ameyibor, E.; Fu, W.; Gardet-Salvi, L.; Stritt-Etter, A. L.; Schurmann, P.; Knaff, D. B.; Johnson, M. K. Biochemistry 1996, 35, 11425
30. Staples, C. R.; Gaymard, E.; Stritt-Etter, A. L.; Telser, J.; Hoffman, B. M.; Schurmann, P.; Knaff, D. B.; Johnson, M. K. Biochemistry 1998, 37, 4612
31. Walters, E. M.; Garcia-Serres, R.; Jameson, G. N.; Glauser, D. A.; Bourquin, F.; Manieri, W.; Schurmann, P.; Johnson, M. K.; Huynh, B. H. J. Am. Chem. Soc. 2005, 127, 9612
32. Wang, W.; Li, J.; Wang, K.; Huang, C.; Zhang, Y.; Oldfield, E. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 11189
33. Wang, W.; Wang, K.; Li, J.; Nellutla, S.; Smirnova, T. I.; Oldfield, E. J. Am. Chem. Soc. 2011, 133, 8400
34. Xu, W.; Lees, N. S.; Hall, D.; Welideniya, D.; Hoffman, B. M.; Duin, E. C. Biochemistry 2012, 51, 4835
35. Liu, Y. L.; Guerra, F.; Wang, K.; Wang, W.; Li, J.; Huang, C.; Zhu, W.; Houlihan, K.; Li, Z.; Zhang, Y.; Nair, S. K.; Oldfield, E. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 8558
36. Schmidt, T. G.; Skerra, A. Nat. Protoc. 2007, 2, 1528
37. Stoll, S.; Schweiger, A. J. Magn. Reson. 2006, 178, 42
38. Bernstein, F. C.; Koetzle, T. F.; Williams, G. J.; Meyer, E. F., Jr; Brice, M. D.; Rodgers, J. R.; Kennard, O.; Shimanouchi, T.; Tasumi, M. Eur. J. Biochem. 1977, 80, 319
39. Kabsch, W. J. Appl. Crystallogr. 1993, 26, 795
40. Brunger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Acta Crystallogr., Sect. D 1998, 54, 905
41. Emsley, P.; Cowtan, K. Acta Crystallogr., Sect. D 2004, 60, 2126
42. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr., Sect. D 1997, 53, 240
43. Perrakis, A.; Harkiolaki, M.; Wilson, K. S.; Lamzin, V. S. Acta Crystallogr., Sect. D 2001, 57, 1445
44. PyMOL, v1.5.0.1; Schrödinger, LLC, 2012, http://www.pymol.org.
45. Laskowski, R. A.; Rullmann, J. A.; MacArthur, M. W.; Kaptein, R.; Thornton, J. M. J. Biomol. NMR 1996, 8, 477
46. Hecht, S.; Amslinger, S.; Jauch, J.; Kis, K.; Trentinaglia, V.; Adam, P.; Eisenreich, W.; Bacher, A.; Rohdich, F. Tetrahedron Lett. 2002, 43, 8929
47. Fox, D. T.; Poulter, C. D. J. Org. Chem. 2002, 67, 5009