Nitrile hydration by thiolate- and alkoxide-ligated co-NHase analogues. Isolation of Co(III)-amidate and Co(III)-iminol intermediates

Journal of the American Chemical Society

Volumn 133, Issue 11, 2011, Pages 3954-3963

  Swartz, Rodney D ^a   Coggins, Michael K ^a   Kaminsky, Werner ^a   Kovacs, Julie A ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY E; ALKOXIDES; AMIDATE; BOND ACTIVATION; C-O BOND FORMATION; COORDINATION SPHERE; ENZYMATIC REACTION; H-BONDING NETWORKS; HYDROGEN BONDINGS; INTERMEDIATE STRUCTURES; KINETIC DATA; NITRILE HYDRATASES; ORDERS OF MAGNITUDE; REACTION COORDINATES; SERINE RESIDUES; THIOLATES;

ACTIVATION ENERGY; AMIDES; AMINO ACIDS; BIOMIMETICS; COORDINATION REACTIONS; CYANIDES; ENZYMES; HYDRATES; HYDRATION; IRON COMPOUNDS; REACTION INTERMEDIATES; REACTION KINETICS; SPHERES;

COBALT COMPOUNDS;

ALKOXIDE; ALKYL GROUP; CARBON; COBALT COMPLEX; HYDROGEN; HYDROXIDE; METHANOL; NITRILE; NITRILE HYDRATASE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CRYSTALLOGRAPHY; HYDRATION; HYDROGEN BOND; SYNTHESIS;

COBALT; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NITRILES; THERMODYNAMICS; WATER;

EID: 79952753594     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja108749f     Document Type: Article

References (43)

1. Kukukshkin, V. Y.; Pombeiro, A. J. L. Inorg. Chim. Acta 2005, 358, 1-21
2. Breslow, R.; Fairweather, R.; Keana, J. J. Am. Chem. Soc. 1967, 89, 2135-2138
3. Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723-729
4. Chin, J.; Kim, J. H. Angew. Chem., Int. Ed. 1990, 29, 523-525
5. Kim, J. H.; Britten, J.; Chin, J. J. Am. Chem. Soc. 1993, 115, 3618-3622
6. Gonzalez, G.; Moullet, B.; Martinez, M.; Merbach, A. E. Inorg. Chem. 1994, 33, 2330
7. Miyanaga, A.; Fushinobu, S.; Ito, K.; Wakagi, T. Biochem. Biophys. Res. Commun. 2001, 288, 1169-1174
8. Payne, M. S.; Wu, S.; Fallon, R. D.; Tudor, G.; Stieglitz, B.; Turner, I. M. J.; Nelson, M. J. Biochemistry 1997, 36, 5447-5454
9. Brennan, B. A.; Alms, G.; Scarrow, R. C. J. Am. Chem. Soc. 1996, 118, 9194-9195
10. Kobayashi, M.; Nishiyama, M.; Nagasawa, T.; Horinouchi, S.; Beppu, T.; Yamada, H. Biochim. Biophys. Acta 1991, 1129, 23-33
11. Mitra, S.; Holz, R. C. J. Biol. Chem. 2007, 282, 7397-7404
12. Nojiri, M.; Nakayama, H.; Odaka, M.; Yohda, M.; Takio, K.; Endo, I. FEBS Lett. 2000, 465, 173-177
13. Nagashima, S.; Nakasako, M.; Naoshi, D.; Tsujimura, M.; Takio, K.; Odaka, M.; Yohda, M.; Kamiya, N.; Endo, I. Nat. Struct. Biol. 1998, 5, 347-351
14. Huang, W.; Jia, J.; Cummings, J.; Nelson, M.; Schneider, G.; Lindqvist, Y. Structure 1997, 5, 691-699
15. Lugo-Mas, P.; Dey, A.; Xu, L.; Davin, S. D.; Benedict, J.; Kaminsky, W.; Hodgson, K. O.; Hedman, B.; Solomon, E. I.; Kovacs, J. A. J. Am. Chem. Soc. 2006, 128, 11211-11221
16. Shearer, J.; Kung, I. Y.; Lovell, S.; Kaminsky, W.; Kovacs, J. A. J. Am. Chem. Soc. 2001, 123, 463-468
17. Brines, L. M.; Villar-Acevedo, G.; Kitagawa, T.; Swartz, R. D.; Lugo-Mas, P.; Kaminsky, W.; Benedict, J. B.; Kovacs, J. A. Inorg. Chim. Acta 2008, 361, 1070-1078
18. Rabinovitch, B. S.; Winkler, C. A. Can. J. Research 1949, 20B, 185-188
19. Buckingham, D. A.; Keene, F. R.; Sargeson, A. M. J. Am. Chem. Soc. 1973, 17, 5649-5652
20. Kovacs, J. A. Chem. Rev. 2004, 104, 825-848
21. Kobayashi, M.; Shimizu, S. Nat. Biotechnol. 1998, 16, 733-736
22. Rao, S.; Holz, R. C. Biochemistry 2008, 47, 12057-12064
23. Kobayashi, M.; Nagasawa, T.; Yamada, H. Tibtech 1992, 10, 402-408
24. Yamanaka, Y.; Hashimoto, K.; Ohtaki, A.; Noguchi, K.; Yohda, M.; Odaka, M. J. Biol. Inorg. Chem. 2010, 15, 655-665
25. Sugiura, Y.; Kuwahara, J.; Nagasawa, T.; Yamada, H. J. Am. Chem. Soc. 1987, 109, 5848-5850
26. Kukushkin, V. Y.; Pombeiro, A. J. L. Chem. Rev. 2002, 102, 1771-1802
27. Balahura, R. J.; Cock, P.; Purcell, W. L. J. Am. Chem. Soc. 1974, 96, 2739-2742
28. Zanella, A. W.; Ford, P. C. Inorg. Chem. 1975, 14, 42-47
29. Noveron, J. C.; Olmstead, M. M.; Mascharak, P. K. J. Am. Chem. Soc. 1999, 121, 3553-3554
30. Heinrich, L.; Mary-Verla, A.; Li, Y.; Vaissermann, J.; Chottard, J. C. Eur. J. Inorg. Chem. 2001, 2203-2206
31. Brines, L. M.; Shearer, J.; Fender, J. K.; Schweitzer, D.; Shoner, S. C.; Barnhart, D.; Kaminsky, W.; Lovell, S.; Kovacs, J. A. Inorg. Chem. 2007, 46, 9267-9277
32. Based on a survey of the Cambridge Crystallographic Database.
33. Schneider, M.; Ferguson, G.; Balahura, R. Can. J. Chem. 1973, 51, 2180
34. Noveron, J. C.; Olmstead, M. M.; Mascharak, P. K. J. Am. Chem. Soc. 2001, 123, 3247-3259
35. Drago, R. S. Physical Methods for Chemists; 2 nd ed.; Saunders: Orlando, FL, 1992.
36. Fairlie, D. P.; Woon, T. C.; Wickramasinghe, W. A.; Willis, A. C. Inorg. Chem. 1994, 33, 6425-6428
37. Sigel, H.; Martin, R. B. Chem. Rev. 1982, 82, 385
38. Nagao, H.; Hirano, T.; Tsuboya, N.; Shiota, S.; Mukaida, M.; Oi, T.; Yamasaki, M. Inorg. Chem. 2002, 41, 6267-6273
39. Cini, R.; Fanizzi, F. P.; Intini, F. P.; Maresca, L.; Natile, G. J. Am. Chem. Soc. 1993, 115, 5123-5131
40. Suh, M. P.; Oh, K. Y.; Lee, J. W.; Bae, Y. Y. J. Am. Chem. Soc. 1996, 118, 777-783
41. Cini, R.; Fanizzi, F. P.; Intini, F. P.; Natile, G. J. Am. Chem. Soc. 1991, 113, 7805-7806
42. Zobel, D., Luger, P., Dreissig, W., and Koritsanszky, T. Acta Crystallogr., Sect. B 1992, 48, 837
43. March, J. Advanced Organic Chemistry; John Wiley and Sons: New York, 1985.