N-Substituted Derivatives of the Azadithiolate Cofactor from the [FeFe] Hydrogenases: Stability and Complexation

Inorganic Chemistry

Volumn 54, Issue 12, 2015, Pages 5717-5724

  Angamuthu, Raja ^a,b   Chen, Chi Shian ^a   Cochrane, Tyler R ^a   Gray, Danielle L ^a   Schilter, David ^a   Ulloa, Olbelina A ^a   Rauchfuss, Thomas B ^a  

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

^b INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

COENZYME; HYDROGENASE; IRON HYDROGENASE; IRON SULFUR PROTEIN; NICKEL; ORGANOMETALLIC COMPOUND; THIOL DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COENZYME; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; COENZYMES; CRYSTALLOGRAPHY, X-RAY; HYDROGENASE; HYDROLYSIS; IRON-SULFUR PROTEINS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; SULFHYDRYL COMPOUNDS;

EID: 84935910585     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/acs.inorgchem.5b00290     Document Type: Article

References (50)

1. Nicolet, Y.; Lemon, B. J.; Fontecilla-Camps, J. C.; Peters, J. W. Trends Biochem. Sci. 2000, 25, 138-143
2. Barton, B. E.; Olsen, M. T.; Rauchfuss, T. B. J. Am. Chem. Soc. 2008, 130, 16834-16835
3. Carroll, M. E.; Barton, B. E.; Rauchfuss, T. B.; Carroll, P. J. J. Am. Chem. Soc. 2012, 134, 18843-18852
4. Camara, J. M.; Rauchfuss, T. B. J. Am. Chem. Soc. 2011, 133, 8098-8101
5. Camara, J. M.; Rauchfuss, T. B. Nat. Chem. 2012, 4, 26-30
6. Nicolet, Y.; de Lacey, A. L.; Vernede, X.; Fernandez, V. M.; Hatchikian, E. C.; Fontecilla-Camps, J. C. J. Am. Chem. Soc. 2001, 123, 1596-1601
7. Bullock, R. M.; Appel, A. M.; Helm, M. L. Chem. Commun. 2014, 50, 3125-3143
8. DuBois, D. L. Inorg. Chem. 2014, 53, 3935-3960
9. Shook, R. L.; Borovik, A. S. Inorg. Chem. 2010, 49, 3646-3660
10. Silakov, A.; Wenk, B.; Reijerse, E.; Lubitz, W. Phys. Chem. Chem. Phys. 2009, 11, 6592-6599
11. Lubitz, W.; Ogata, H.; Rüdiger, O.; Reijerse, E. Chem. Rev. 2014, 114, 4081-4148
12. Stich, T. A.; Myers, W. K.; Britt, R. D. Acc. Chem. Res. 2014, 47, 2235-2243
13. Myers, W. K.; Stich, T. A.; Suess, D. L. M.; Kuchenreuther, J. M.; Swartz, J. R.; Britt, R. D. J. Am. Chem. Soc. 2014, 136, 12237-12240
14. Berggren, G.; Adamska, A.; Lambertz, C.; Simmons, T. R.; Esselborn, J.; Atta, M.; Gambarelli, S.; Mouesca, J.-M.; Reijerse, E.; Lubitz, W.; Happe, T.; Artero, V.; Fontecave, M. Nature 2013, 499, 66-69
15. 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.; Happe, T. Nat. Chem. Biol. 2013, 9, 607-609
16. Siebel, J. F.; Adamska-Venkatesh, A.; Weber, K.; Rumpel, S.; Reijerse, E.; Lubitz, W. Biochem. 2015, 54, 1474-1483
17. Lawrence, J. D.; Li, H.; Rauchfuss, T. B.; Bénard, M.; Rohmer, M.-M. Angew. Chem., Int. Ed. 2001, 40, 1768-1771
18. Li, H.; Rauchfuss, T. B. J. Am. Chem. Soc. 2002, 124, 726-727
19. Angamuthu, R.; Carroll, M. E.; Ramesh, M.; Rauchfuss, T. B. Eur. J. Inorg. Chem. 2011, 2011, 1029-1032
20. Wang, Z.; Liu, J.-H.; He, C.-J.; Jiang, S.; Åkermark, B.; Sun, L.-C. J. Organomet. Chem. 2007, 692, 5501-5507
21. Das, P.; Capon, J.-F.; Gloaguen, F.; Pétillon, F. Y.; Schollhammer, P.; Talarmin, J.; Muir, K. W. Inorg. Chem. 2004, 43, 8203-8205
22. Gao, S.; Fan, J.; Sun, S.; Peng, X.; Zhao, X.; Hou, J. Dalton Trans. 2008, 2128-2135
23. Lysenko, N. M. Zh. Org. Khim. 1974, 10, 2049
24. Izawa, T.; Terao, Y.; Suzuki, K. Tetrahedron: Asymmetry 1997, 8, 2645-2648
25. Lin, T.; Ulloa, O. A.; Rauchfuss, T. B.; Gray, D. L. Eur. J. Inorg. Chem. 2014, 2014, 4109-4114
26. Zhu, W.; Marr, A. C.; Wang, Q.; Neese, F.; Spencer, D. J. E.; Blake, A. J.; Cooke, P. A.; Wilson, C.; Schröder, M. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 18280-18285
27. Bourrez, M.; Steinmetz, R.; Gloaguen, F. Inorg. Chem. 2014, 53, 10667-10673
28. Fraze, K.; Wilson, A. D.; Appel, A. M.; Rakowski DuBois, M.; DuBois, D. L. Organometallics 2007, 26, 3918-3924
29. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley-Interscience: New York, 1999
30. Hartung, R.; Golz, G.; Schlaf, S.; Silvennoinen, G.; Polborn, K.; Mayer, P.; Pfaendler, H. R. Synthesis 2009, 495-501.
31. Tard, C.; Pickett, C. J. Chem. Rev. 2009, 109, 2245-2274
32. Böhme, H.; Hartke, K. Chem. Ber. 1963, 96, 604-606
33. Böhme, H.; Kietz, K.; Leidreiter, K. D. Arch. Pharm. 1954, 287, 198-209
34. Wellmar, U. J. Heterocycl. Chem. 1998, 35, 1531-1532
35. Miyazawa, S.; Ikeda, K.; Achiwa, K.; Sekiya, M. Chem. Lett. 1984, 785-788
36. Rakhimova, E. B.; Vasil'yeva, I. V.; Khalilov, L. M.; Ibragimov, A. G.; Dzhemilev, U. M. Chem. Heterocycl. Compd. 2012, 48, 1050-1057
37. Murzakova, N. N.; Prokof'ev, K. I.; Tyumkina, T. V.; Ibragimov, A. G. Russ. J. Org. Chem. 2012, 48, 588-593
38. Stanley, J. L.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 2007, 26, 1907-1911
39. Song, L.-C.; Wang, L.-X.; Yin, B.-S.; Li, Y.-L.; Zhang, X.-G.; Zhang, Y.-W.; Luo, X.; Hu, Q. M. Eur. J. Inorg. Chem. 2008, 2008, 291-297
40. Rauchfuss, T. B.; Roundhill, D. M. J. Am. Chem. Soc. 1975, 97, 3386-3392
41. Kochem, A.; Weyhermüller, T.; Neese, F.; van Gastel, M. Organometallics 2015, 34, 995-1000
42. Gan, L.; Groy, T. L.; Tarakeshwar, P.; Mazinani, S. K. S.; Shearer, J.; Mujica, V.; Jones, A. K. J. Am. Chem. Soc. 2015, 137, 1109-1115
43. Swanson, K. D.; Duffus, B. R.; Beard, T. E.; Peters, J. W.; Broderick, J. B. Eur. J. Inorg. Chem. 2011, 2011, 935-947
44. Dinis, P.; Suess, D. L. M.; Fox, S. J.; Harmer, J. E.; Driesener, R. C.; De La Paz, L.; Swartz, J. R.; Essex, J. W.; Britt, R. D.; Roach, P. L. Proc. Nat. Acad. Sci. U.S.A. 2015, 00, 0000
45. Peters, J. W.; Broderick, J. B. Annu. Rev. Biochem. 2012, 81, 429-450
46. Fugate, C. J.; Stich, T. A.; Kim, E. G.; Myers, W. K.; Britt, R. D.; Jarrett, J. T. J. Am. Chem. Soc. 2012, 134, 9042-9045
47. Jarrett, J. T. In Iron-Sulfur Clusters in Chemistry and Biology; Rouault, T. A., Ed.; Walter de Gruyter: Berlin, Germany, 2014; pp 107-131.
48. Mityuk, A. P.; Denisenko, A. V.; Dacenko, O. P.; Grygorenko, O. O.; Mykhailiuk, P. K.; Volochnyuk, D. M.; Shishkin, O. V.; Tolmachev, A. A. Synthesis 2010, 2010, 493-497
49. Cadenas-Pliego, G.; Jésus Rosales-Hoz, M. d.; Contreras, R.; Flores-Parra, A. Tetrahedron: Asym. 1994, 5, 633-640
50. Beermann, C.; Ramloch, H. Ger. Offen. DE1915898, 1970.