Table of Contents Author Guidelines Submit a Manuscript
Bioinorganic Chemistry and Applications
Volume 2016, Article ID 3585781, 10 pages
http://dx.doi.org/10.1155/2016/3585781
Research Article

Reversible Oxygenation of α-Amino Acid–Cobalt(II) Complexes

1Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education and Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi, Xinjiang 830046, China
2College of Chemistry and Chemical Engineering, Central South University, Changsha, Hunan 410083, China

Received 27 October 2015; Revised 21 December 2015; Accepted 22 December 2015

Academic Editor: Luigi Casella

Copyright © 2016 Xincun Zhang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. W. Nam, Y.-M. Lee, and S. Fukuzumi, “Tuning reactivity and mechanism in oxidation reactions by mononuclear nonheme iron(IV)-oxo complexes,” Accounts of Chemical Research, vol. 47, no. 4, pp. 1146–1154, 2014. View at Publisher · View at Google Scholar · View at Scopus
  2. K. P. Bryliakov and E. P. Talsi, “Active sites and mechanisms of bioinspired oxidation with H2O2, catalyzed by non-heme Fe and related Mn complexes,” Coordination Chemistry Reviews, vol. 276, pp. 73–96, 2014. View at Publisher · View at Google Scholar · View at Scopus
  3. S. Kim, J. W. Ginsbach, A. I. Billah et al., “Tuning of the copper-thioether bond in tetradentate N3S(thioether) Ligands; O–O bond reductive cleavage via a [CuII2(μ-1,2-peroxo)]2+/[CuIII2(μ-oxo)2]2+ equilibrium,” Journal of the American Chemical Society, vol. 136, no. 22, pp. 8063–8071, 2014. View at Publisher · View at Google Scholar
  4. D. Das, Y.-M. Lee, K. Ohkubo, W. Nam, K. D. Karlin, and S. Fukuzumi, “Temperature-independent catalytic two-electron reduction of dioxygen by ferrocenes with a copper(II) tris[2-(2-pyridyl)ethyl]amine catalyst in the presence of perchloric acid,” Journal of the American Chemical Society, vol. 135, no. 7, pp. 2825–2834, 2013. View at Publisher · View at Google Scholar · View at Scopus
  5. S. Fukuzumi, L. Tahsini, Y.-M. Lee, K. Ohkubo, W. Nam, and K. D. Karlin, “Factors that control catalytic two-versus four-electron reduction of dioxygen by copper complexes,” Journal of the American Chemical Society, vol. 134, no. 16, pp. 7025–7035, 2012. View at Publisher · View at Google Scholar · View at Scopus
  6. M. Baumgarten, C. J. Winscom, and W. Lubitz, “Probing the surrounding of a cobalt(II) porphyrin and its superoxo complex by EPR techniques,” Applied Magnetic Resonance, vol. 20, no. 1-2, pp. 35–70, 2001. View at Publisher · View at Google Scholar · View at Scopus
  7. N. Kindermann, S. Dechert, S. Demeshko, and F. Meyer, “Proton-induced, reversible interconversion of a μ-1,2-peroxo and a μ-1,1-hydroperoxo dicopper(II) complex,” Journal of the American Chemical Society, vol. 137, no. 25, pp. 8002–8005, 2015. View at Publisher · View at Google Scholar
  8. M. Rolff and F. Tuczek, “How do copper enzymes hydroxylate aliphatic substrates? Recent insights from the chemistry of model systems,” Angewandte Chemie—International Edition, vol. 47, no. 13, pp. 2344–2347, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. B. M. T. Lam, J. A. Halfen, V. G. Young Jr. et al., “Ligand macrocycle structural effects on copper–dioxygen reactivity,” Inorganic Chemistry, vol. 39, no. 18, pp. 4059–4072, 2000. View at Publisher · View at Google Scholar · View at Scopus
  10. J. P. Klinman, “How do enzymes activate oxygen without inactivating themselves?” Accounts of Chemical Research, vol. 40, no. 5, pp. 325–333, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. M. R. Tiné, “Cobalt complexes in aqueous solutions as dioxygen carriers,” Coordination Chemistry Reviews, vol. 256, no. 1-2, pp. 316–327, 2012. View at Publisher · View at Google Scholar · View at Scopus
  12. A. M. J. Devoille and J. B. Love, “Double-pillared cobalt Pacman complexes: synthesis, structures and oxygen reduction catalysis,” Dalton Transactions, vol. 41, no. 1, pp. 65–72, 2012. View at Publisher · View at Google Scholar · View at Scopus
  13. M. Tonigold, Y. Lu, A. Mavrandonakis et al., “Pyrazolate-based cobalt(II)-containing metal-organic frameworks in heterogeneous catalytic oxidation reactions: elucidating the role of entatic states for biomimetic oxidation processes,” Chemistry—A European Journal, vol. 17, no. 31, pp. 8671–8695, 2011. View at Publisher · View at Google Scholar · View at Scopus
  14. S. Hong, H. So, H. Yoon et al., “Reactivity comparison of high-valent iron(iv)-oxo complexes bearing N-tetramethylated cyclam ligands with different ring size,” Dalton Transactions, vol. 42, no. 22, pp. 7842–7845, 2013. View at Publisher · View at Google Scholar · View at Scopus
  15. S. P. de Visser, J.-U. Rohde, Y.-M. Lee, J. Cho, and W. Nam, “Intrinsic properties and reactivities of mononuclear nonheme iron–oxygen complexes bearing the tetramethylcyclam ligand,” Coordination Chemistry Reviews, vol. 257, no. 2, pp. 381–393, 2013. View at Publisher · View at Google Scholar · View at Scopus
  16. J. Cho, R. Sarangi, and W. Nam, “Mononuclear metal–O2 complexes bearing macrocyclic N-tetramethylated cyclam ligands,” Accounts of Chemical Research, vol. 45, no. 8, pp. 1321–1330, 2012. View at Publisher · View at Google Scholar · View at Scopus
  17. J. Cho, R. Sarangi, H. Y. Kang et al., “Synthesis, structural, and spectroscopic characterization and reactivities of mononuclear cobalt(III)-peroxo complexes,” Journal of the American Chemical Society, vol. 132, no. 47, pp. 16977–16986, 2010. View at Publisher · View at Google Scholar · View at Scopus
  18. A. Kunishita, M. Z. Ertem, Y. Okubo et al., “Active site models for the CuA site of peptidylglycine α-hydroxylating monooxygenase and dopamine β-monooxygenase,” Inorganic Chemistry, vol. 51, no. 17, pp. 9465–9480, 2012. View at Publisher · View at Google Scholar · View at Scopus
  19. M. Martinho, G. Blain, and F. Banse, “Activation of dioxygen by a mononuclear non-heme iron complex: characterization of a FeIII(OOH) intermediate,” Dalton Transactions, vol. 39, no. 6, pp. 1630–1634, 2010. View at Publisher · View at Google Scholar · View at Scopus
  20. J. A. Kovacs, “How iron activates O2,” Science, vol. 299, no. 5609, pp. 1024–1025, 2003. View at Publisher · View at Google Scholar · View at Scopus
  21. J. Park, Y. Morimoto, Y.-M. Lee, W. Nam, and S. Fukuzumi, “Unified view of oxidative C-H bond cleavage and sulfoxidation by a nonheme iron(IV)-oxo complex via lewis acid-promoted electron transfer,” Inorganic Chemistry, vol. 53, no. 7, pp. 3618–3628, 2014. View at Publisher · View at Google Scholar · View at Scopus
  22. J. Park, Y.-M. Lee, W. Nam, and S. Fukuzumi, “Brønsted acid-promoted C–H bond cleavage via electron transfer from toluene derivatives to a protonated nonheme iron(IV)-oxo complex with no kinetic isotope effect,” Journal of the American Chemical Society, vol. 135, no. 13, pp. 5052–5061, 2013. View at Publisher · View at Google Scholar · View at Scopus
  23. N. Kitajima and Y. Moro-oka, “Copper-dioxygen complexes. Inorganic and bioinorganic perspectives,” Chemical Reviews, vol. 94, no. 3, pp. 737–757, 1994. View at Publisher · View at Google Scholar · View at Scopus
  24. E. C. Niederhoffer, J. H. Timmons, and A. E. Martell, “Thermodynamics of oxygen binding in natural and synthetic dioxygen complexes,” Chemical Reviews, vol. 84, no. 2, pp. 137–203, 1984. View at Publisher · View at Google Scholar · View at Scopus
  25. A. L. Gavrilova, C. J. Qin, R. D. Sommer, A. L. Rheingold, and B. Bosnich, “Bimetallic reactivity. One-site addition two-metal oxidation reaction of dioxygen with a bimetallic dicobalt(II) complex bearing five- and six-coordinate sites,” Journal of the American Chemical Society, vol. 124, no. 8, pp. 1714–1722, 2002. View at Publisher · View at Google Scholar · View at Scopus
  26. X. Zhang, H. Furutachi, S. Fujinami et al., “Structural and spectroscopic characterization of (μ-hydroxo or μ-oxo)(μ-peroxo)diiron(III) complexes: models for peroxo intermediates of non-heme diiron proteins,” Journal of the American Chemical Society, vol. 127, no. 3, pp. 826–827, 2005. View at Publisher · View at Google Scholar · View at Scopus
  27. J. Simplicio and R. G. Wilkins, “Kinetics of the rapid interaction of bis(histidinato)-cobalt(II) with oxygen,” Journal of the American Chemical Society, vol. 89, no. 24, pp. 6092–6095, 1967. View at Publisher · View at Google Scholar · View at Scopus
  28. F. Yue, N. Song, Y. Huang et al., “Reversible oxygenation of bis[β-(2-pyridyl)-α-alaninato]Co(II) complex in aqueous solution at room temperature,” Inorganica Chimica Acta, vol. 398, pp. 141–146, 2013. View at Publisher · View at Google Scholar · View at Scopus
  29. J. F. Li, J. H. Fu, C. X. Wang, H. Li, and J. D. Wang, “Oxygenation reaction and aging mechanism of the triethylenetetramine cobalt complex,” Chinese Journal of Inorganic Chemistry, vol. 31, no. 4, pp. 673–680, 2015. View at Google Scholar
  30. E. Vinck, E. Carter, D. M. Murphy, and S. Van Doorslaer, “Observation of an organic acid mediated spin state transition in a Co(II)-Schiff base complex: an EPR, HYSCORE, and DFT study,” Inorganic Chemistry, vol. 51, no. 15, pp. 8014–8024, 2012. View at Publisher · View at Google Scholar · View at Scopus
  31. C. Comuzzi, A. Melchior, P. Polese, R. Portanova, and M. Tolazzi, “Cobalt(II) dioxygen carriers based on simple diamino ligands: kinetic and ab initio studies,” Inorganic Chemistry, vol. 42, no. 25, pp. 8214–8222, 2003. View at Publisher · View at Google Scholar · View at Scopus
  32. D. Burk, J. Z. Hearon, L. Caroline, and A. L. Schade, “Reversible complexes of cobalt, histidine, and oxygen gas,” The Journal of Biological Chemistry, vol. 165, no. 2, pp. 723–724, 1946. View at Google Scholar · View at Scopus
  33. M. S. Michailidis and R. B. Martin, “Oxygenation and oxidation of cobalt(II) chelates of amines, amino acids, and dipeptides,” Journal of the American Chemical Society, vol. 91, no. 17, pp. 4683–4689, 1969. View at Publisher · View at Google Scholar · View at Scopus
  34. W. R. Harris, G. McLendon, and A. E. Martell, “Oxygenation equilibriums of cobalt(II) complexes of amino acids and dipeptides,” Journal of the American Chemical Society, vol. 98, no. 26, pp. 8378–8381, 1976. View at Publisher · View at Google Scholar · View at Scopus
  35. H. M. Wen, X. Zhang, H. Li, F. Yue, and J. D. Wang, “Contrast study of the oxygenation of Co(II) complexes with different bi-/poly-dentate ligands,” Chemical Journal of Chinese Universities, vol. 34, no. 10, pp. 2262–2269, 2013. View at Google Scholar
  36. X. C. Zhang, F. Yue, Y. Huang et al., “Reversible oxygenation properties of 2,3-diaminopropanoic acid cobalt complex,” Chinese Journal of Inorganic Chemistry, vol. 29, no. 11, pp. 2387–2393, 2013. View at Google Scholar
  37. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., GAUSSIAN 03, Revision E.01, Gaussian, Inc., Wallingford, Conn, USA, 2004.
  38. R. D. Hancock and A. E. Martell, “Ligand design for selective complexation of metal ions in aqueous solution,” Chemical Reviews, vol. 89, no. 8, pp. 1875–1914, 1989. View at Publisher · View at Google Scholar · View at Scopus
  39. Y. L. Deng, Y. Yang, and F. Yue, “Coordination environmeng influence to the oxygenation performance of alanine cobalt,” Computers and Applied Chemistry, vol. 31, no. 3, pp. 325–328, 2014. View at Google Scholar
  40. Y. Yang, Y. L. Deng, F. Yue, H. M. Chen, D. C. Sun, and J. D. Wang, “Theoretical research of cobalt(II)-hisditine oxygenation process,” Computers and Applied Chemistry, vol. 30, no. 6, pp. 633–637, 2013. View at Google Scholar