A three-coordinate copper(I)-phenoxide complex that models the reduced form of galactose oxidase

Abstract

A novel 3-coordinate Cu(I)-phenoxide complex with N-donor supporting ligation was structurally characterized and shown to be highly reactive towards dioxygen, similar to the reduced form of galactose oxidase.

References

1. J. W. Whittaker, in Metalloenzymes Involving Amino Acid Residue and Related Radicals, ed. H. Sigel and A. Sigel, Marcel Dekker, New York, 1994.
2. (a) M. M. Whittaker and J. W. Whittaker, J. Biol. Chem., 1990, 265, 9610; (b) M. L. McGlashen, D. D. Eads, T. G. Spiro and J. W. Whittaker, J. Phys. Chem., 1995, 99, 4918; (c) A. J. Baron, C. Stevens, C. Wilmot, K. D. Seneviratne, V. Blakeley, D. M. Dooley, S. E. V. Phillips, P. F. Knowles and M. J. McPherson, J. Biol. Chem., 1994, 269, 25095; (d) P. F. Knowles, R. D. Brown III, S. H. Koenig, S. Wang, R. A. Scott, M. A. McGuirl, D. E. Brown and D. M. Dooley, Inorg. Chem., 1995, 34, 3895; (e) N. Ito, S. E. V. Phillips, K. D. S. Yadav and P. F. Knowles, J. Mol. Biol., 1994, 238, 794; (f) M. P. Reynolds, A. J. Baron, C. M. Wilmot, E. Vinecombe, C. Stevens, S. E. V. Philips, P. F. Knowles and M. J. McPherson, J. Biol. Inorg. Chem., 1997, 2, 327; (g) K. Clark, J. E. Penner-Hahn, M. Whittaker and J. W. Whittaker, Biochemistry, 1994, 33, 12553.
3. M. M. Whittaker, P. J. Kersten, N. Nakamura, J. Sanders-Loehr, E. S. Schweizer and J. W. Whittaker, J. Biol. Chem., 1996, 271, 681.
4. J. Stubbe and W. A. van der Donk, Chem. Rev., 1998, 98, 705.
5. (a) M. M. Whittaker, D. P. Ballou and J. W. Whittaker, Biochemistry, 1998, 37, 8426; (b) B. P. Branchaud, M. P. Montague-Smith, D. J. Kosman and F. R. McLaren, J. Am. Chem. Soc., 1993, 115, 798; (c) R. M. Wachter, M. P. Montague-Smith and B. P. Branchaud, J. Am. Chem. Soc., 1997, 119, 7743; (d) C. G. Saysell, T. Barna, C. D. Borman, A. J. Baron, M. J. McPherson and A. G. Sykes, J. Biol. Inorg. Chem., 1997, 2, 702.
6. Selected recent references: (a) J. A. Halfen, V. G. Young, Jr. and W. B. Tolman, Angew. Chem., Int. Ed. Engl., 1996, 35, 1687; (b) Y. Wang and T. D. P. Stack, J. Am. Chem. Soc., 1996, 118, 13097; (c) M. M. Whittaker, W. R. Duncan and J. W. Whittaker, Inorg. Chem., 1996, 35, 382; (d) J. A. Halfen, B. A. Jazdzewski, S. Mahapatra, L. M. Berreau, E. C. Wilkinson, L. Que, Jr. and W. B. Tolman, J. Am. Chem. Soc., 1997, 119, 8217; (e) A. Sokolowski, H. Leutbecher, T. Weyhermüller, R. Schnepf, E. Bothe, E. Bill, P. Hildebrandt and K. Wieghardt, J. Biol. Inorg. Chem., 1997, 2, 444; (f) D. Zurita, I. Gautier-Luneau, S. Ménage, J.-L. Pierre and E. Saint-Aman, J. Biol. Inorg. Chem., 1997, 2, 46; (g) Y. Wang, J. L. DuBois, B. Hedman, K. O. Hodgson and T. D. P. Stack, Science, 1998, 279, 537; (h) S. Itoh, S. Takayama, R. Arakawa, A. Furuta, M. Komatsu, A. Ishida, S. Takamuku and S. Fukuzumi, Inorg. Chem., 1997, 36, 1407; (i) J. Müller, T. Weyhermüller, E. Bill, P. Hildebrandt, L. Ould-Moussa, T. Glaser and K. Wieghardt, Angew. Chem., Int. Ed. Engl., 1998, 37, 616.
7. A search of the Cambridge Crystallographic Database (vol. 5.15 April 1998) revealed only two reports of X-ray structures of monomeric Cu(I) phenolates: (a) P. Fiaschi, C. Floriani, M. Pasquali, A. Chiesi-Villa and C. Guastini, J. Chem. Soc., Chem. Commun., 1984, 888; (b) T. N. Sorrell, A. S. Borovik and C. C. Shen, Inorg. Chem., 1986, 25, 589.
8. Selected examples: (a) R. R. Gagné, R. P. Kreh and J. A. Dodge, J. Am. Chem. Soc., 1979, 101, 6917; (b) T. N. Sorrell and A. S. Borovik, J. Chem. Soc., Chem. Commun., 1984, 1489; (c) T. N. Sorrell, C. C. Shen and C. J. O'Connor, Inorg. Chem., 1987, 26, 1755; (d) K. D. Karlin, R. W. Cruse, Y. Gultneh, A. Farooq, J. C. Hayes and J. Zubieta, J. Am. Chem. Soc., 1987, 109, 2668.
9. Synthesized via a modification of the procedure reported in: R. P. Houser, V. G. Young, Jr. and W. B. Tolman, J. Am. Chem. Soc., 1996, 118, 11555.
10. A. Sokolowski, J. Müller, T. Weyhermüller, R. Schnepf, P. Hildebrandt, K. Hildenbrand, E. Bothe and K. Wieghardt, J. Am. Chem. Soc., 1997, 119, 8889.
11. E. M. Meyer, S. Gambarotta, C. Floriani, A. Chiesi-Villa and C. Guastini, Organometallics, 1989, 8, 1067.
12. A similar pattern of divergent bond distances has been seen in another T-shaped Cu(I) complex: J. V. Dagdigian, V. McKee and C. A. Reed, Inorg. Chem., 1982, 21, 1332.
13. A search of the Cambridge Crystallographic Database (vol. 5.15, April 1998) for Cu–N distances in 3-coordinate Cu complexes gave 161 structures with mean Cu–N = 1.988 Å(standard deviation 0.092 Å).
14. The ferrocene–ferrocenium couple under identical conditions had E_1/2= 0.55 V, close to the literature value of 0.56 V: N. G. Connelly and W. E. Geiger, Chem. Rev., 1996, 96, 877.
15. (a) N. Kitajima and Y. Moro-oka, Chem. Rev., 1994, 94, 737; (b) K. D. Karlin, Z. Tyeklár and A. D. Zuberbühler, in Bioinorganic Catalysis, ed. J. Reedijk, Marcel Dekker, New York, 1993, pp. 261–315.
16. We thank the NIH (GM47365.), the NSF (NYI Award to W. B. T.), and the Sloan and Camille and Henry Dreyfus Foundations (fellowships to W. B. T.) for funding this research.