Electronic Effects in Oxidation Reactions Utilizing Dinuclear Copper Complexes with the Bis[3-(2-hydroxybenzylideneamino)phenyl] Sulfone Ligand
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Baron AJ, Stevens C, Wilmot C, Seneviratne KD, Blakeley V, Dooley DM, et al. Structure and Mechanism of Galactose Oxidase. The Free Radical Site. J Biol Chem. 1994 Oct 7; 269(40):25095-25105.
Burton SG. Biocatalysis with polyphenoloxidase: a review. Catal Today. 1994; 22:459-87.
Cahoy J, Holland PL, Tolman WB. Experimental Studies of the Interconversion of Peroxo- and Bis(oxo)Dicopper Complexes. Inorg Chem. 1999; 38:2161-2168.
Chiacchierini E, Restuccia D, Vinci G. Bioremediation of Food Industry Effluents: Recent Applications of Free and Immobilised Polyphenoloxidases. Food Sci Tech Int. 2004; 10(6):373-382.
Decker H, Tuczek F. Tyrosinase/
Catecholoxidase Activity of Hemocyanins: Structural Basis and Molecular Mechanism. Trends Biochem Sci. 2000; 25:392-397.
Duran N, Rosa MA, D’Annibale A, Gianfreda L. Application of laccases and tyrosinases (phenoloxidases) immobilised on different supports: a review. Enzyme Microb Technol. 2002; 31:907-31.
Estiu G. Recent Calculations in Proteins and Metalloenzymes In the frontiers of chemistry and biophysics [Internet]. [Place unknown]: [Publisher unknown]; 2004 Apr. Available from: http://www.qtp.ufl.edu/~kmmprogs/
Fenton D. Biocoordination Chemistry. New York: Oxford University Press; 1995.
Funabiki, T, editor. Oxygenases and Model Systems. Dordrecht: Kluwer Academic Publishers; 1997.
Funaki T, Takanohashi Y, Fukazawa H, Kuruma I. Estimation of kinetic parameters in the inactivation of an enzyme by a suicide substrate. Biochim Biophys Acta 1991; 1078:43-46.
Gamez P, Koval IA, Reedijk J. Bio-mimicking galactose oxidase and hemocyanin, two dioxygen-processing copper proteins. Dalton Trans. 2004 Dec 21; (24):4079-88.
Gerdemann C, Eicken C, Krebs B. The crystal structure of catechol oxidase: new insight into the function of type-3 copper proteins. Acc Chem Res. 2002; 35:183-191.
Guidote AM, Ando K, Kurusu Y, Nagao H, Masuyama Y. Synthesis and characterization of homodinuclear manganese and cobalt complexes bridged by a hemiacetal or by an acetate group in a µ-(η2:η1) bridging mode. Inorg Chim Acta. 2001; 314:27-36.
Guidote AM, Ando K, Terada K, Kurusu Y, Nagao H, Masuyama Y. Synthesis, characterization and reactivity of a series of dinuclear copper complexes bearing the ligand bis[3-(2-bydroxybenzylideneamino)phenyl] sulfone and derivatives. Inorg Chim Acta. 2001; 324:203-211.
Holland PL, Rodgers KR, Tolman WB. Is the Bis(Oxo)Dicopper Core Capable of Hydroxylating an Arene? Angew Chem Int Ed. 1999; 38:1139-1142.
Ikehata K, Nicell JA. Characterisation of tyrosinase for the treatment of aqueous phenols. Bioresour Technol. 2000; 74:191-9.
Karlin KD, Cruse RW, Gultneh Y. Dioxygen–copper reactivity: a hydroperoxo–dicopper(II) complex. J Chem Soc Chem Commun. 1987; 599-600.
Karlin KD, Ghosh P, Cruse RW, Rarooq A, Gultneh Y, Jacobson RR, et al. Dioxygen-copper reactivity: generation, characterization, and reactivity of a hydroperoxodicopper(II) complex. J Am Chem Soc. 1988; 110:6769-6780.
Khenkin AM, Efremenko I, Weiner, L., Martin JML, Neumann R. Photochemical Reduction of Carbon Dioxide Catalyzed by a Ruthenium-Substituted Polyoxometalate. Chem Eur J. 2010; 16(4):1356-1364.
Kitajima N, Moro-oka Y. Copper-dioxygen Complexes. Inorganic and Bioorganic Perspectives. Chem Rev. 1994; 94:737-757.
Kleifeld O, Frenkel A, Martin JM, Sagi I. Active site electronic structure and dynamics during metalloenzyme catalysis. Nat Struct Biol. 2003 Feb; 10(2):98-103.
Lewis EA, Tolman WB. Reactivity of Dioxygen-Copper Systems. Chem. Rev. 2004; 104:1047-1076.
Liang HC, Zhang CX, Henson MJ, Sommer RD, Hatwell KR, Kaderli S, et al. Contrasting Copper-Dioxygen Chemistry Arising from Alike Tridentate Alkyltriamine Copper (I) Complexes. J Am Chem Soc. 2002; 124:4170-4171.
Magnus KA, Ton-that H, Carpenter JE. Recent Structural Work on the Oxygen Transport Protein Hemocyanin. Chem Rev. 1994; 94:727-735.
Mcmurry J, Simanek E. Fundamentals of Organic Chemistry. 6th Ed. California: Thomson Brooks/Cole; 2007. p. 242-243.
Mirica LM, Otttenwaelder X, Stack TDP. Structure and Spectroscopy of Copper-Dioxygen Complexes. Chem Rev. 2004; 104:1013-1045.
Mirica LM, Vance M, Rudd DJ, Hedman B, Hodgson KO, Solomon EI, et al. A Stabilized µ-η2:η2-Peroxodicopper(II) Complex with a Secondary Diamine Ligand and Its Tyrosinase-like Reactivity. J Am Chem Soc. 2002; 124:9332-9333.
Ottenwaelder X, Rudd DJ, Corbett MC, Hodgson KO, Hedman B, Stack TDP. Reversible O-O Bond Cleavage in Copper-Dioxygen Isomers: Impact of Anion Basicity. J Am Chem Soc. 2006; 128:9268-9269.
Panek JJ, Ward TR, Jezierska-Mazzarello A, Novič. Flexibility of a biotinylated ligand in artificial metalloenzymes based on streptavidin—an insight from molecular dynamics simulations with classical and ab initio force fields. J Comput Aided Mol Des. 2010 Sep; 24(9):719-732.
Punniyamurthy T, Velusamy S, Iqbal J. Recent Advances in Transition Metal Catalyzed Oxidation of Organic Substrates with Molecular Oxygen. Chem Rev. 2005; 105(6):2329-2364.
Robb DA. Tyrosinase. In: Lontie R, editor. Copper proteins and copper enzyme, Vol. II. Boca Raton, FL: CRC Press; 1984. p. 208–40.
Rompel A, Fischer H, Meiwes D, Büldt-karentzopoulos K, Dillinger R, Tuczek F, et al. Purification and spectroscopic studies on catechol oygenases from Lycopus europaeus and Populus nigra: evidence for a dinuclear center of type 3 and spectroscopic similarities to tyrosinase and hemocyanin. J Biol Inorg Chem. 1999; 4:56-63.
Simándi LI, editor. Advances in Catalytic Activation of Dioxygen by Metal Complexes. London: Kluwer Academic Publishers; 2003.
Solomon EI, Chen P, Metz M, Lee SK, Palmer AE. Oxygen Binding, Activation, and Reduction to Water by Copper Proteins. Angew Chem Int Ed. 2001; 40:4570-4590.
Solomon EI, Sundaram UM, Manchokin TE. Multicopper oxidases and oxygenases. Chem Rev. 1996; 96:2563-2606.
Tolman WB. Using synthetic chemistry to understand copper protein active sites: a personal perspective. J Biol Inorg Chem. 2006 Apr;11(3):261-71.
Wang RX, You XZ, Meng QJ, Mintz EA, Bu XR. A Modified Synthesis of o-Hydroxyaryl Aldehydes. Synth Commun. 1994; 24:1757-1760.
Wang YD, Dubois JL, Hedman B, Hodgson KO, Stack TDP. Catalytic galactose oxidase models: Biomimetic Cu(II)-phenoxyl-radical reactivity. Science. 1998; 279:537-540.
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