Mononuclear copper(ll)-superoxo complexes that mimic the structure andreactivity of the active centers of PHM and DβM

Journal of the American Chemical Society

Volumn 131, Issue 8, 2009, Pages 2788-2789

  Kunishita, Atsushi ^b   Kubo, Mmoru ^c   Sugimoto, Hideki ^b   Ogura, Takashi ^c   Sato, Kazunobu ^b   Takui, Takeji ^b   Itoh, Shinobu ^a,b,d  

^a OSAKA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

^c UNIVERSITY OF HYOGO   (Japan)

^d INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CENTER; CH-BOND ACTIVATION; MONONUCLEAR COPPER; MONOOXYGENASES; STARTING MATERIALS; SUPEROXO COMPLEX; TETRAHEDRAL GEOMETRY; TRIDENTATE LIGANDS;

CHEMICAL BONDS; COPPER;

COPPER COMPOUNDS;

CARBON; COPPER; COPPER COMPLEX; CUPROUS ION; DOPAMINE BETA MONOOXYGENASE; HYDROGEN; LIGAND; METHANE HYDROGEN NITROGEN DIOXIDE[ 1 ( 2 PARA METHANE HYDROGEN NITROGEN DIOXIDE PHENETHYL) 5 ( 2 PYRIDIN 2 YLETHYL) 1,5 DIAZACYCLOOCTANE; OXYGEN; PEPTIDYLGLYCINE ALPHA HYDROXYLATING MONOOXYGENASE; PYRIDINE DERIVATIVE; SOLVENT; TRIDENTATE LIGAND; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; BIOMIMETIC MATERIAL; CYCLOOCTANE DERIVATIVE; MIXED FUNCTION OXIDASE; MULTIENZYME COMPLEX; ORGANOMETALLIC COMPOUND; PEPTIDYLGLYCINE MONOOXYGENASE; SUPEROXIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; GEOMETRY; HYDROGEN BOND; HYDROXYLATION; MOLECULAR MIMICRY; STOICHIOMETRY; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON SPIN RESONANCE; METABOLISM; STRUCTURE ACTIVITY RELATION;

BIOMIMETIC MATERIALS; CATALYTIC DOMAIN; COPPER; CYCLOOCTANES; DOPAMINE BETA-HYDROXYLASE; ELECTRON SPIN RESONANCE SPECTROSCOPY; LIGANDS; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; MULTIENZYME COMPLEXES; ORGANOMETALLIC COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDES;

EID: 68049099373     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja809464e     Document Type: Article

References (30)

1. Itoh, S. Curr. Opin. Chem. Biol. 2006, 10, 115-122.
2. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev.2004, 104, 1013-1046.
3. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104,1047-1076.
4. Rolff, M.; Tuczek, F. Angew. Chem., Int. Ed. 2008, 47, 2344-2347.
5. Klinman, J. P. Chem. Rev. 1996, 96, 2541-2561.
6. Francisco, W. AT.; Wille, G.; Smith, A. J.; Merkler, D. J.; Klinman, J.P. J. Am. Chem. Soc. 2004. 126, 13168-13169.
7. Chen, P.; Solomon, E. I. J. Am. Chem. Soc. 2004,126, 4991-5000.
8. Yoshizawa, K.; Kihara, N.; Kamachi, T.; Shiota, Y. Inorg Chem.2006, 45, 3034-3041.
9. Gherman. B. F.; Heppenr, D. E.; Tolman, W. B.; Cramer, C. J. J. Biol.Inorg. Chem. 2006, 11, 197-205.
10. Crespo, A.; Marti, M. A.; Roitberg, A. E.; Amzel, L. M.; Estrin, D. A.J. Am Chem. Soc. 2006, 128, 12817-12828.
11. (11)prigge, S. T.; Eipper, B. A.; Mains, R. E.; Amzel, L. M.Science 2004, 394, 836-837.
12. (a) Fujisawa, K.; Tanaka, M.; Moro-oka. Y; Kitajima. N. J. Am. Chem.Soc. 1994, 116, 12079-12080.
13. (b) Chen, P.; Root, D, E.; Campochiano, C; Fujisawa. K.; Solomon. E. I.J. Am. Chem. Soc. 2003, 125, 466-474.
14. (a) Cramer, C. J.; Tolman, W. B Acc. Chem. Res. 2007,40, 601-608.
15. (c) Hong, S.; Huber, S. M.; Gagliardi,L; Cramer, C. C; Tolman, W. B.J. Am. Chem. Soc. 2007, 129, 14190-14192.
16. (a) Fujii, T.; Yamaguchi, S.; Funahashi, Y.; Ozawa, T.; Tosha. T.;Kitagawa. T.; Masuda, H. Chem. Commun. 2006, 4428-4430.
17. (b) Fujii, T.; Yamaguchi, S.; Hirota, S.; Masuda, H. Dalton Trans.2008. 164-170.
18. (a) Izzet, G.; Zeitouny, J. Akdas-Killig, H.; Frapart, Y.; Ménage.S.; Douziech, B.; Jabin, I.; Le Mest, Y.; Reinaud, O. J. Am. Chem. Soc.2008. 130, 9514-9523.
19. (b) Lande, A.; Parisel. O.; Gerard. H.; Moliner, V.; Reinaud, O.Chem.- Eur. J. 2008, 14, 6465-6473.
20. Würtele, C.; Gaoutchenova, E.; Harms, K.; Holthausen, M.;Sundermeyer, J.; Schindler, S. Angew. Chem., Int. Ed. 2006,45, 3867-3869.
21. (a) Maiti, D.; Fry. H. C; Woertink, J. S.; Vance, M. A.; Solomon, E. I.;Karlin, K. D. J.Am. Chem. Soc. 2007, 129, 264-265.
22. (b) Maiti, D.; Lee. D.; Gaoutchenova. K.; Würtele, C; Holthausen, M.C: Sarjeant. A. A. N.; Sundermever, J.; Schindler, S.; Karlin, K. D. Angew.Chem., Int. Ed. 2008, 47, 82-85.
23. (c) Maiti, D.; Lee, D.; Sarjeant. A. A. N.; Pau, M. Y. M.; Gaoutchenova.K.; Sundermeyer, J.; Karlin. K. D. J. Am. Chem. Soc. 2008.130, 6700-6701.
24. Jazdzewski, B. A.; Reynolds, A. M.; Holland, P. L.; Young. V. G. Jr.;Kaderli. S.; Zuberbühler, A. D.; Tolman, W. B. J. Biol. Inorg. Chem.2003. 8, 381-393.
25. Komiyama, K.; Furutachi, H.; Nagatomo, S.; Hashimoto. A.; Hayashi. H.;Fujinami. S.; Suzuki. M.; Kitagawa. T. Bull. Chem. Soc. Jpn. 2004,77. 59-72.
26. Lanci. M. P.; Smirnov, V. V.; Cramer, C. J.; Gauchenova, E. V.;Sundermeyer. J.; Roth, J. P. J. Am. Chem. Soc. 2007. 129,14697-14709.
27. 13 observed a ligand hydroxylationreaction in the oxygenation of a mononuclear copper(I) complex supported by thecalix[6]arene-tren ligand. They suggested that the active oxygen species was amononuclear copper(II)-superoxo intermediate, but direct detection of such anintermediate was unsuccessful.
28. 2 (Figure S14). as inthe case of other end-on superoxo copper(II) complexes.
29. x when argon gaswas flashed onto the solution at-70 °C.
30. Bencini, A.; Gatteschi. D. EPR of Exchange Coupled Systems;Springer-Verlag: New York, 1990; p 167.