Reduction of fluorinated cyclopropene by nitrogenase

Journal of the American Chemical Society

Volumn 135, Issue 28, 2013, Pages 10346-10352

  Ni, Feng ^a   Lee, Chi Chung ^b   Hwang, Candy S ^a   Hu, Yilin ^b   Ribbe, Markus W ^b   Mckenna, Charles E ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALTERNATIVE SUBSTRATES; BOND CLEAVAGES; C-C BOND CLEAVAGES; CIS AND TRANS ISOMERS; CYCLOPROPENES; FE-PROTEINS; HYDRIDE TRANSFERS; REDUCTION MECHANISMS;

CARBON; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROPYLENE; PROTEINS; SUBSTRATES;

REDUCTION;

2 FLUOROPROPENE; 3,3 DIFLUOROCYCLOPROPENE; ADENOSINE TRIPHOSPHATE; CARBON; CYCLOPROPENE; DEUTERIUM; DITHIONITE; NITROGENASE; PROPYLENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CIS ISOMER; DEUTERON NUCLEAR MAGNETIC RESONANCE; ENZYME SUBSTRATE; MASS FRAGMENTOGRAPHY; PROTEIN CLEAVAGE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; TRANS ISOMER;

CYCLOPROPANES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITROGENASE; OXIDATION-REDUCTION;

EID: 84880337544     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3121058     Document Type: Article

References (43)

1. In Catalysts for Nitrogen Fixation: Nitrogenases, Relevant Chemical Models and Commercial Processes; Smith, B., Richards, R. L., Newton, W. E., Eds.; Kluwer Academic Publishers: Dordrecht, 2004; p 1-340.
2. Seefeldt, L. C.; Hoffman, B. M.; Dean, D. R. Annu. Rev. Biochem. 2009, 78, 701-722
3. Hoffman, B. M.; Dean, D. R.; Seefeldt, L. C. Acc. Chem. Res. 2009, 42, 609-619
4. Hoffman, B. M.; Lukoyanov, D.; Dean, D. R.; Seefeldt, L. C. Acc. Chem. Res. 2013, 46, 587-595
5. Thorneley, R. N. F.; Lowe, D. J. In Molybdenum enzymes; Spiro, T. G., Ed.; John Wiley and Sons: Chichester, 1985; pp 221-284.
6. Dance, I. J. Am. Chem. Soc. 2007, 129, 1076-1088
7. Lee, C. C.; Hu, Y.; Ribbe, M. W. Science 2010, 329, 642
8. Hu, Y.; Lee, C. C.; Ribbe, M. W. Science 2011, 333, 753-755
9. Yang, Z. Y.; Dean, D. R.; Seefeldt, L. C. J. Biol. Chem. 2011, 286, 19417-19421
10. Hardy, R. W. F.; Burns, R. C. Annu. Rev. Biochem. 1968, 37, 331-358
11. McKenna, C. E.; McKenna, M. C.; Higa, M. T. J. Am. Chem. Soc. 1976, 98, 4657-4659
12. McKenna, C. E.; Huang, C. W. Nature 1979, 280, 609-611
13. McKenna, C. E.; Jones, J. B.; Eran, H.; Huang, C. W. Nature 1979, 280, 611-612
14. McKenna, C. E.; McKenna, M. C.; Huang, C. W. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 4773-4777
15. McKenna, C. E.; Simeonov, A. M.; Eran, H.; Bravo-Leerabhandh, M. Biochemistry 1996, 35, 4502-4514
16. McKenna, C. E.; Simeonov, A. M. Dimethyldiazenes are Reduced by Nitrogenase: Implications for the Mechanism of Substrate Binding and Reduction at the Active Site. In Nitrogen Fixation: Fundamentals and Applications; Tikhonovich, I. A.; Provorov, N. A.; Romanov, V. I.; Newton, W. E., Eds.; Kluwer Academic Publishers: Dordrecht, 1995.
17. Simeonov, A. M. Ph.D. Dissertation, University of Southern California, 1998; p 242.
18. Barney, B. M.; Yang, T.-C.; Igarashi, R. Y.; Dos Santos, P. C.; Laryukhin, M.; Lee, H.-I.; Hoffman, B. M.; Dean, D. R.; Seefeldt, L. C. J. Am. Chem. Soc. 2005, 127, 14960-14961
19. Barney, B. M.; Lukoyanov, D.; Yang, T.-C.; Dean, D. R.; Hoffman, B. M.; Seefeldt, L. C. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 17113-17118
20. Lukoyanov, D.; Dikanov, S. A.; Yang, Z. Y.; Barney, B. M.; Samoilova, R. I.; Narasimhulu, K. V.; Dean, D. R.; Seefeldt, L. C.; Hoffman, B. M. J. Am. Chem. Soc. 2011, 133, 11655-11664
21. Berkowitz, D. B.; Karukurichi, K. R.; de la Salud-Bea, R.; Nelson, D. L.; McCune, C. D. J. Fluorine Chem. 2008, 129, 731-742
22. Yamazaki, T.; Taguchi, T.; Ojima, I. Unique Properties of Fluorine and their Relevance to Medicinal Chemistry and Chemical Biology. In Fluorine in Medicinal Chemistry and Chemical Biology; Oijima, I., Ed.; John Wiley & Sons: Chichester, 2009; pp 1-46.
23. Murphy, C. D. Biotechnol. Lett. 2010, 32, 351-359
24. Natarajan, R.; Azerad, R.; Badet, B.; Copin, E. J. Fluorine Chem. 2005, 126, 425-436
25. Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373-431
26. Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119-2183
27. Clot, E.; Eisenstein, O.; Jasim, N.; Macgregor, S. A.; McGrady, J. E.; Perutz, R. N. Acc. Chem. Res. 2011, 44, 333-348
28. Lukoyanov, D.; Yang, Z. Y.; Barney, B. M.; Dean, D. R.; Seefeldt, L. C.; Hoffman, B. M. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 5583-5587
29. McKenna, C. E.; Eran, H.; Nakajima, T.; Osumi, A. Curr. Persp. Nitrogen Fixation 1981, 358
30. Wells, A. F. Structural Inorganic Chemistry; Clarendon Press: Oxford, 1984.
31. Baird, M. C. J. Magn. Reson. 1974, 14, 117-120
32. Dolbier, W. R. J.; Battiste, M. A. Chem. Rev. 2003, 103, 1071-1098
33. Wiberg, K. B.; Marquez, M. J. Am. Chem. Soc. 1998, 120, 2932-2938
34. McBee, E. T.; Roberts, C. W.; Judd, G. F.; Chao, T. S. J. Am. Chem. Soc. 1955, 77, 1292-1293
35. Benton, P. M.; Christiansen, J.; Dean, D. R.; Seefeldt, L. C. J. Am. Chem. Soc. 2001, 123, 1822-1827
36. 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, 9563-9569
37. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117-3179
38. Vela, J.; Smith, J. M.; Yu, Y.; Ketterer, N. A.; Flaschenriem, C. J.; Lachicotte, R. J.; Holland, P. L. J. Am. Chem. Soc. 2005, 127, 7857-7870
39. Seefeldt, L. C.; Hoffman, B. M.; Dean, D. R. Curr. Opin. Chem. Biol. 2012, 16, 19-25
40. Lukoyanov, D.; Yang, Z. Y.; Dean, D. R.; Seefeldt, L. C.; Hoffman, B. M. J. Am. Chem. Soc. 2010, 132, 2526-2527
41. Boll, M.; Fuchs, G. Eur. J. Biochem. 1995, 234, 921-933
42. Smoukov, S. K.; Kopp, D. A.; Valentine, A. M.; Davydov, R.; Lippard, S. J.; Hoffman, B. M. J. Am. Chem. Soc. 2002, 124, 2657-2663
43. Wiig, J. A.; Lee, C. C.; Fay, A. W.; Hu, Y. L.; Ribbe, M. W. Methods Mol. Biol. 2011, 766, 93-103-103