Synthetic and Structural Studies of 2-Acylmethyl-6-R-Difunctionalized Pyridine Ligand-Containing Iron Complexes Related to [Fe]-Hydrogenase

Inorganic Chemistry

Volumn 55, Issue 3, 2016, Pages 1258-1269

  Song, Li Cheng ^a   Xu, Kai Kai ^a   Han, Xiao Feng ^a   Zhang, Ji Wei ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGENASE; IRON DERIVATIVE; IRON HYDROGENASE; IRON SULFUR PROTEIN; LIGAND;

CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; METABOLISM; SYNTHESIS;

HYDROGENASE; IRON COMPOUNDS; IRON-SULFUR PROTEINS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE;

EID: 84956688157     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/acs.inorgchem.5b02490     Document Type: Article

References (51)

1. Adams, M. W. W.; Stiefel, E. I. Science 1998, 282, 1842-1843 10.1126/science.282.5395.1842
2. Cammack, R. Nature 1999, 397, 214-215 10.1038/16601
3. Lubitz, W.; Ogata, H.; Rüdiger, O.; Reijerse, E. Chem. Rev. 2014, 114, 4081-4148 10.1021/cr4005814
4. Simmons, T. R.; Berggren, G.; Bacchi, M.; Fontecave, M.; Artero, V. Coord. Chem. Rev. 2014, 270-271, 127-150 10.1016/j.ccr.2013.12.018
5. Nicolet, Y.; Lemon, B. J.; Fontecilla-Camps, J. C.; Peters, J. W. Trends Biochem. Sci. 2000, 25, 138-143 10.1016/S0968-0004(99)01536-4
6. Evans, D. J.; Pickett, C. J. Chem. Soc. Rev. 2003, 32, 268-275 10.1039/b201317g
7. Lubitz, W.; Reijerse, E.; van Gastel, M. Chem. Rev. 2007, 107, 4331-4365 10.1021/cr050186q
8. Fontecilla-Camps, J. C.; Volbeda, A.; Cavazza, C.; Nicolet, Y. Chem. Rev. 2007, 107, 4273-4303 10.1021/cr050195z
9. Shima, S.; Thauer, R. K. Chem. Rec. 2007, 7, 37-46 10.1002/tcr.20111
10. Dey, S.; Das, P. K.; Dey, A. Coord. Chem. Rev. 2013, 257, 42-63 10.1016/j.ccr.2012.04.021
11. Zirngibl, C.; Hedderich, R.; Thauer, R. K. FEBS Lett. 1990, 261, 112-116 10.1016/0014-5793(90)80649-4
12. Corr, M. J.; Murphy, J. A. Chem. Soc. Rev. 2011, 40, 2279-2292 10.1039/c0cs00150c
13. Schultz, K. M.; Chen, D.; Hu, X. Chem.-Asian J. 2013, 8, 1068-1075 10.1002/asia.201300232
14. Lyon, E. J.; Shima, S.; Boecher, R.; Thauer, R. K.; Grevels, F. W.; Bill, E.; Roseboom, W.; Albracht, S. P. J. J. Am. Chem. Soc. 2004, 126, 14239-14248 10.1021/ja046818s
15. Shima, S.; Lyon, E. J.; Sordel-Klippert, M.; Kauß, M.; Kahnt, J.; Thauer, R. K.; Steinbach, K.; Xie, X. L.; Verdier, L.; Griesinger, C. Angew. Chem., Int. Ed. 2004, 43, 2547-2551 10.1002/anie.200353763
16. Shima, S.; Lyon, E. J.; Thauer, R. K.; Mienert, B.; Bill, E. J. Am. Chem. Soc. 2005, 127, 10430-10435 10.1021/ja051895o
17. Shima, S.; Pilak, O.; Vogt, S.; Schick, M.; Stagni, M. S.; Meyer-Klaucke, W.; Warkentin, E.; Thauer, R. K.; Ermler, U. Science 2008, 321, 572-575 10.1126/science.1158978
18. Shima, S.; Chen, D.; Xu, T.; Wodrich, M. D.; Fujishiro, T.; Schultz, K. M.; Kahnt, J.; Ataka, K.; Hu, X. Nat. Chem. 2015, 7, 995-1002 10.1038/nchem.2382
19. Hiromoto, T.; Ataka, K.; Pilak, O.; Vogt, S.; Stagni, M. S.; Meyer-Klaucke, W.; Warkentin, E.; Thauer, R. K.; Shima, S.; Ermler, U. FEBS Lett. 2009, 583, 585-590 10.1016/j.febslet.2009.01.017
20. Tamura, H.; Salomone-Stagni, M.; Fujishiro, T.; Warkentin, E.; Meyer-Klaucke, W.; Ermler, U.; Shima, S. Angew. Chem., Int. Ed. 2013, 52, 9656-9659 10.1002/anie.201305089
21. Guo, Y.; Wang, H.; Xiao, Y.; Vogt, S.; Thauer, R. K.; Shima, S.; Volkers, P. I.; Rauchfuss, T. B.; Pelmenschikov, V.; Case, D. A.; Alp, E. E.; Sturhahn, W.; Yoda, Y.; Cramer, S. P. Inorg. Chem. 2008, 47, 3969-3977 10.1021/ic701251j
22. Wang, X.; Li, Z.; Zeng, X.; Luo, Q.; Evans, D. J.; Pickett, C. J.; Liu, X. Chem. Commun. 2008, 3555-3557 10.1039/b805262j
23. Liu, T.; Li, B.; Popescu, C. V.; Bilko, A.; Pérez, L. M.; Hall, M. B.; Darensbourg, M. Y. Chem.-Eur. J. 2010, 16, 3083-3089 10.1002/chem.200902684
24. Royer, A. M.; Rauchfuss, T. B.; Gray, D. L. Organometallics 2009, 28, 3618-3620 10.1021/om9004059
25. Royer, A. M.; Salomone-Stagni, M.; Rauchfuss, T. B.; Meyer-Klaucke, W. J. Am. Chem. Soc. 2010, 132, 16997-17003 10.1021/ja1072228
26. Turrell, P. J.; Wright, J. A.; Peck, J. N. T.; Oganesyan, V. S.; Pickett, C. J. Angew. Chem., Int. Ed. 2010, 49, 7508-7511 10.1002/anie.201004189
27. Chen, D.; Scopelliti, R.; Hu, X. Angew. Chem., Int. Ed. 2011, 50, 5671-5673 10.1002/anie.201100201
28. Chen, D.; Scopelliti, R.; Hu, X. Angew. Chem., Int. Ed. 2012, 51, 1919-1921 10.1002/anie.201107634
29. Hu, B.; Chen, D.; Hu, X. Chem.-Eur. J. 2013, 19, 6221-6224 10.1002/chem.201300495
30. Song, L.-C.; Xie, Z.-J.; Wang, M.-M.; Zhao, G.-Y.; Song, H.-B. Inorg. Chem. 2012, 51, 7466-7468 10.1021/ic301146u
31. Tanino, S.; Ohki, Y.; Tatsumi, K. Chem.-Asian J. 2010, 5, 1962-1964 10.1002/asia.201000408
32. Song, L.-C.; Zhao, G.-Y.; Xie, Z.-J.; Zhang, J.-W. Organometallics 2013, 32, 2509-2512 10.1021/om400240e
33. Song, L.-C.; Hu, F.-Q.; Wang, M.-M.; Xie, Z.-J.; Xu, K.-K.; Song, H.-B. Dalton Trans. 2014, 43, 8062-8071 10.1039/c4dt00335g
34. Song, L.-C.; Hu, F.-Q.; Zhao, G.-Y.; Zhang, J.-W.; Zhang, W.-W. Organometallics 2014, 33, 6614-6622 10.1021/om5009296
35. Turrell, P. J.; Hill, A. D.; Ibrahim, S. K.; Wright, J. A.; Pickett, C. J. Dalton Trans. 2013, 42, 8140-8146 10.1039/c3dt50642h
36. Hu, B.; Chen, D.; Hu, X. Chem.-Eur. J. 2014, 20, 1677-1682 10.1002/chem.201304290
37. Kalz, K. F.; Brinkmeier, A.; Dechert, S.; Mata, R. A.; Meyer, F. J. Am. Chem. Soc. 2014, 136, 16626-16634 10.1021/ja509186d
38. Chong, D.; Georgakaki, I. P.; Mejia-Rodriguez, R.; Sanabria-Chinchilla, J.; Soriaga, M. P.; Darensbourg, M. Y. Dalton Trans. 2003, 4158-4163 10.1039/b304283a
39. Chen, D.; Scopelliti, R.; Hu, X. Angew. Chem., Int. Ed. 2010, 49, 7512-7515 10.1002/anie.201004579
40. Calderazzo, F. Angew. Chem., Int. Ed. Engl. 1977, 16, 299-311 10.1002/anie.197702991
41. Berke, H.; Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 7224-7235 10.1021/ja00491a018
42. Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books, Mill Valley, CA, 1980.
43. Seyferth, D.; Womack, G. B.; Song, L.-C. Organometallics 1983, 2, 776-779 10.1021/om00078a019
44. Wayland, E. N. Organic Syntheses; Wiley: New York, 1988; Vol. 6, p 807.
45. Zhou, H.-B.; Liu, G.-S.; Yao, Z.-J. Org. Lett. 2007, 9, 2003-2006 10.1021/ol0706307
46. Ramachandran, J.; Ramadas, S. R.; Pillai, C. N. Org. Prep. Proced. Int. 1981, 13, 71-79 10.1080/00304948109356098
47. Lubenets, V. I.; Stadnitskaya, N. E.; Novikov, V. P. Russ. J. Electrochem. 2000, 36, 851-853 10.1007/BF02757443
48. Ozer, H.; Kocakaya, S. O.; Akgun, A.; Hoşgören, H.; Togrul, M. Tetrahedron: Asymmetry 2009, 20, 1541-1546 10.1016/j.tetasy.2009.06.010
49. CrystalClear and Crystalstructure; Rigaku and Rigaku Americas: The Woodlands, TX, 2007.
50. Sheldrick, G. M. SHELXS97, a Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997.
51. Sheldrick, G. M. SHELXL97, a Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.