Model studies of methyl CoM reductase: Methane formation via CH 3-S bond cleavage of Ni(I) tetraazacyclic complexes having intramolecular methyl sulfide pendants

Inorganic Chemistry

Volumn 51, Issue 9, 2012, Pages 5173-5187

  Nishigaki, Jun Ichi ^a   Matsumoto, Tsuyoshi ^a   Tatsumi, Kazuyuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETIC MATERIAL; CYCLAM; HETEROCYCLIC COMPOUND; METHANE; METHYL COENZYME M REDUCTASE; NICKEL; ORGANOMETALLIC COMPOUND; OXIDOREDUCTASE; SULFIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON SPIN RESONANCE; ENZYME ACTIVE SITE; SYNTHESIS;

AZA COMPOUNDS; BIOMIMETIC MATERIALS; CATALYTIC DOMAIN; ELECTRON SPIN RESONANCE SPECTROSCOPY; HETEROCYCLIC COMPOUNDS; METHANE; MODELS, MOLECULAR; NICKEL; ORGANOMETALLIC COMPOUNDS; OXIDOREDUCTASES; SULFIDES;

EID: 84860698747     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic300017k     Document Type: Article

References (56)

1. Grabarse, W.; Shima, S.; Mahlert, F.; Duin, E. C.; Thauer, R. K.; Ermler, U. In Handbook of Metalloproteins; Messershmidt, A., Huber, R., Poulos, T., Wieghardt, K., Eds.; John Wiley & Sons: New York, 2001; Vol. 2, pp 897-914.
2. DiMarco, A. A.; Bobik, T. A.; Wolfe, R. S. Annu. Rev. Biochem. 1990, 59, 355-394
3. Gunsalus, R. P.; Wolfe, R. S. FEMS Microbiol. Lett. 1978, 3, 191-193
4. Ellefson, W. L.; Whitman, W. B.; Wolfe, R. S. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 3707-3710
5. Pfaltz, A.; Livingston, D. A.; Juan, B.; Diekert, G.; Thauer, R. K.; Eschenmoser, A. Helv. Chim. Acta 1985, 68, 1338-1358
6. Halcrow, M. A.; Christou, G. Chem. Rev. 1994, 94, 2421-2481
7. Thauer, R. K. Microbiology 1998, 144, 2377-2406
8. Grabarse, W.; Mahlert, F.; Shima, S.; Thauer, R. K.; Ermler, U. J. Mol. Biol. 2000, 303, 329-344
9. Grabarse, W.; Shima, S.; Goubeaud, M.; Thauer, R. K. Science 1997, 278, 1457-1462
10. Grabarse, W.; Mahlert, F.; Duin, E. C.; Goubeaud, M.; Shima, S.; Thauer, R. K.; Lamzin, V.; Ermler, U. J. Mol. Biol. 2001, 309, 315-330
11. Jaun, B. In Metal Ions in Life Science; Sigel, A.; Sigel, H.; Sigel, R. K. O., Eds.; John Wiley & Sons: Chichester, UK, 2007; Vol. 2, pp 323-356.
12. Albracht, S. P. J.; Ankel-Fuchs, D.; Bocher, R.; Ellennann, J.; Moll, J.; van der Zwaan, J. W.; Thauer, R. K. Biochim. Biophys. Acta 1988, 955, 86-102
13. Albracht, S. P. J.; Ankel-Fuchs, D.; van der Zwaan, J. W.; Fontjin, R. D.; Thauer, R. K. Biochim. Biophys. Acta 1986, 870, 50-57
14. Ermler, U. Dalton Trans. 2005, 3451-3458
15. Färber, G.; Keller, W.; Kratky, C.; Jaun, B.; Pfaltz, A.; Spinner, C.; Kobelt, A.; Eschenmoser, A. Helv. Chim. Acta 1991, 74, 697-716
16. Pfaltz, A.; Jaun, B.; Fässler, A.; Eschenmoser, A.; Jaenchen, R.; Gilles, H. H.; Diekert, G.; Thauer, R. K. Helv. Chim. Acta 1982, 65, 828-865
17. Rospert, S.; Böcher, R.; Albracht, S. P. J.; Thauer, R. K. FEBS Lett. 1991, 291, 371-375
18. Goubeaud, M.; Schreiner, G.; Thauer, R. K. Eur. J. Biochem. 1997, 243, 110-114
19. Telser, J.; Davydov, R.; Horng, Y.-C.; Ragsdale, S. W.; Hoffman, B. M. J. Am. Chem. Soc. 2001, 123, 5853-5860
20. Duin, E. C.; Piskorski, R.; Mahlert, F.; Clay, M. D.; Goenrich, M.; Thauer, R. K.; Jaun, B. J. Biol. Inorg. Chem. 2004, 9, 563-574
21. Mahlert, F.; Bauer, C.; Jaun, B.; Thauer, R. K.; Duin, E. C. J. Biol. Inorg. Chem. 2002, 7, 500-513
22. Zilbermann, I.; Golub, G.; Cohen, H.; Meyerstein, D. Inorg. Chim. Acta 1994, 227, 1-3
23. Signor, L.; Knuppe, C.; Hug, R.; Schweizer, B.; Pfaltz, A.; Jaun, B. Chem.-Eur. J. 2000, 6, 3508-3516
24. Ram, M. S.; Riordan, C. G.; Ostrander, R.; Rheingold, A. L. Inorg. Chem. 1995, 34, 5884-5892
25. Pelmenschikov, V.; Blomberg, M. R. A.; Siegbahn, Per E. M.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 4039-4049
26. Pelmenschikov, V.; Siegbahn, Per E. M. J. Biol. Inorg. Chem. 2003, 8, 653-662
27. Lin, S.-K.; Jaun, B. Helv. Chim. Acta 1992, 75, 1478-1490
28. Jaun, B.; Pfaltz, A. J. Chem. Soc., Chem. Commun. 1986, 293-296
29. A five-coordinated Ni(I) azamacrocyclic complex was reported, see: Suh, M. P.; Oh, K. Y.; Lee, J. W.; Bae, Y. Y. J. Am. Chem. Soc. 1996, 118, 777-783
30. Szalda, D. J.; Fujita, E.; Sanzenbacher, R.; Paulus, H.; Elias, H. Inorg. Chem. 1994, 33, 5855-5863
31. Suh, M. P.; Kim, H. K.; Kim, M. J.; Oh, K. Y. Inorg. Chem. 1992, 3620-3625
32. Furenlid, L. R.; Renner, M. W.; Szalda, D. J.; Fujita, E. J. Am. Chem. Soc. 1991, 113, 883-892
33. Nishigaki, J.; Matsumoto, T.; Tatsumi, K. Eur. J. Inorg. Chem. 2010, 5011-5017
34. Nishigaki, J.; Matsumoto, T.; Tatsumi, K. Inorg. Chem. 2012, 51, 3690-3697.
35. Schmid, C. L.; Kempf, C.; Taubert, A.; Neuburger, M.; Zehnder, M.; Kaden, T. A. Helv. Chim. Acta 1996, 79, 1011-1020
36. Schmid, C.; Neuburger, M.; Zehnder, M.; Kaden, T. A. Helv. Chim. Acta 1997, 80, 241-252
37. Royal, G.; Dahaoui-Gindrey, V.; Dahaoui, S.; Tabart, A.; Guilard, R.; Pullumbi, P.; Lecomte, C. Eur. J. Org. Chem. 1998, 1971-1975
38. The notation of conformation of tetra- or di- N -substituted cyclam takes over that of common cyclam metal complexes, which is determined by the chirality on the nitrogen atoms. See: Bosnich, B.; Poon, C. K.; Tobe, M. L. Inorg. Chem. 1965, 4, 1102-1108
39. Vetrichelvan, M.; Lai, Y.-H.; Mok, K. F. Eur. J. Inorg. Chem. 2004, 10, 2086-2095
40. Ciampolini, M.; Nardi, N.; Dapporto, P.; Zanobini, F. J. Chem. Soc., Dalton Trans. 1984, 995-998
41. Blake, A. J.; Halcrow, M. A.; Schroder, M. J. Chem. Soc., Dalton Trans. 1992, 2803-2808
42. Blake, A. J.; Gould, R. O.; Halcrow, M. A.; Schroder, M. J. Chem. Soc., Dalton Trans. 1993, 2909-2920
43. Piskorski, R.; Jaun, B. J. Am. Chem. Soc. 2003, 125, 13120-13125
44. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910
45. A similar solvent molecule dissociation from Ni(II) cyclam complexes has been reported, see: Boiocchi, M.; Fabbrizzi, L.; Foti, F.; Vázquwz, M. Dalton Trans. 2004, 2616-2620
46. Fox, D. C.; Fiedler, A. T.; Halfen, H. L.; Brunold, T. C.; Halfen, J. A. J. Am. Chem. Soc. 2004, 126, 7627-7636
47. Ram, M. S.; Babac, A.; Espenson, J. H. Inorg. Chem. 1988, 27, 4231-4235
48. Bondi, A. J. Phys. Chem. 1964, 68, 441-451
49. Beley, M.; Collin, J.-P.; Ruppert, R.; Sauvage, J.-P. J. Am. Chem. Soc. 1986, 108, 7461-7467
50. Tada, M.; Masuzawa, Y. Chem. Commun. 1997, 2161-2162
51. Ellison, J. J.; Rhulandt-Senge, K.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1178-1180
52. A related Ni(II) thiolate was reported, see: Halfen, J. A.; Young, V. G., Jr. Chem. Commun. 2003, 2894-2895
53. Ram, R. S.; Bakac, A.; Espenson, J. M. Inorg. Chem. 1986, 25, 3267-3272
54. Bakac, A.; Espenson, J. H. J. Am. Chem. Soc. 1986, 108, 713-719
55. D'Aniello, M. J., Jr.; Barefield, E. K. J. Am. Chem. Soc. 1976, 98, 1610-1612
56. Sunko, D. E.; Branko, J.; Mladen, L. J. Org. Chem. 1987, 52, 2299