銅-胺基酸錯合物活化H2O2之動力學與反應機制探討 ; Kinetics and mechanism of activation of hydrogen peroxide by copper(II) amino acid complexes

郭俊廷 ; Kuo, Chun-Ting ; et al.

In: Ahner, B. A., Lee, J. G., Price, N. M. and Morel, F. M. M. (1998). Phytochelatin concentration in the equatorial Pacific. Deep-Sea Res. I 45, 1779-1796. Akagawa, M. and Suyama, K. (2002). Oxidative deamination by hydrogen peroxide in the presence of metals. Free Radical Research, 36, 13-21. Ali, F. E., Barnham, K. J., Barrow, C. J. and Separovic, F. (2004). Metal catalyzed oxidation of tyrosine residues by different oxidation systems of copper/hydrogen peroxide. Journal of Inorganic Biochemistry 98, 173-184. Baldrian, P., Cajthaml, T., Merhautova, V., Gabriel, J., Nerud, F., Stopka, P., Hruby, M. and Benes, M. J. (2005). Degradation of polycyclic aromatic hydrocarbons by hydrogen peroxide catalyzed by heterogeneous polymeric metal chelates. Applied Catalysis B: Environmental 59, 267-274. Benedito, F. L., Nakagaki, S., Saczk, A. A., Peralta-Zamora, P. G. and Costa, C. M. M. (2003). Study of metalloporphyrin covalently bound to silica as catalyst in the ortho-dianisidine oxidation. Applied Catalysis A 250, 1-11. Cai, R., Kubota, Y. and Fujishima, A. (2003). Effect of copper ions on the formation of hydrogen peroxide from photocatalytic titanium dioxide particles. J. Catalysis 219, 214-218. Chen, L.-H., Liu, L.-Z. and Shen, H.-X. (2003). Mn(II)-sodium dodecyl sulphate complex mimic enzyme-catalyzed fluorescence quenching of Pyronine B by hydrogen peroxide. Analytica Chimica Acta 480, 143-150. EL-Gahami, M. A., Khafagy, Z. A., Ali, A. M. M. and Ismail, N. M. (2004). Thermal, spectroscopic, cyclic voltammetric, and biological activity studies of cobalt(II), nickel(II), and copper(II) complexes of dicarboxylic amino acids and 8-hydroxyquinoline. Journal of Inorganic and Organometallic Polymers 14, 117-129. Fayolle, M. and Romagna, F. (1997). Copper CMP evaluation: planarization issues. Microelectronic Engineering 37/38, 135-141. Felmy, A. R., Girvin, D. C. and Jenne, E. A. (1984). A computer program for calculating aqueous geochemical equilibria. U. S. Environmental Protect Agency, Athens, GA, EPA-600/3-84-032. Gabriel, J., Baldrian, P., Verma, P., Cajthaml, T., Merhautová, V., Eichlerová, I., Stoytchev, I., Trnka, T., Stopka, P. and Nerud, F. (2004). Degradation of BTEX and PAHs by Co(II) and Cu(II)-based radical-generating systems. Applied Catalysis B: Environmental 51, 159-164. Gorantla, V. R. K., Matijevic, E. and Babu, S. V. (2005). Amino acids as complexing agents in chemical-mechanical planarization of copper. Chem. Mater. 17, 2076-2080. Hariharaputhiran, M., Zhang, J., Ramarajan, S., Keleher, J. J. and Li, Y. (2000). Hydroxyl radical formation in H2O2-amino acid mixtures and chemical mechanical polishing of copper. J. Electrochem. Soc. 147, 3820-3826. Hayase, K. and Zeep, R. G. (1991). Photolysis of copper(II)-amino acid complexes in water. Environ. Sci. Technol. 25, 1273-1279. Kato, Y., Kitamoto, N., Kawai, Y. and Osawa, T. (2001). The hydrogen peroxide/copper ion system, but not other metal-catalyzed oxidation systems, produces protein-bound dityrosine. Free Radical Biology & Medicine, 31, 624-632. Lapenna, D., Ciofani, G., Pierdomenico, S. D., Giamberardino, M. A. and Cuccurullo, F. (2005). Copper, zinc superoxide dismutase plus hydrogen peroxide: a catalytic system for human lipoprotein oxidation. FEBS Letters 579, 245-250. Lekchiri, A., Brighli, M., Methenitis, C., Morcellet, J. and Morcellet, M. (1991). Complexation of a polyelectrolyte derived from glutamic acid with copper(II).Catalase-like activity of the complexes. Journal of Inorganic Biochemistry 44, 229-238. Lekchiri, A., Castellano, A., Morcelle, J. and Morcellet, M. (1991). Copper of complexes and catalyse-like activity a polyelectrolyte derived from aspartic acid. Eur. Polym. J. 27, 1271-1278. Lin, T.-Y. and Wu, C.-H. (2005). Activation of hydrogen peroxide in copper(II)/amino acid/H2O2 systems: effects of pH and copper speciation. Journal of Catalysis 232, 117-126. Meng, M.,Chane, T-L., Sun, Y-J. and Hsiao, C-D. (1999). Probing the location and function of the conserved histidine residue of phosphoglucose isomerase by using an active site directed inhibitor N-bromoacetylethanolamine phosphate. Protein Science 8, 2438-2443. Moffett, J. W. and Zika, R. G. (1987). Photochemistry of copper complexes in seawater. Environ. Aqua. Sys Chap9. Moffett, J. W. and Zika, R. G. (1987). Reaction kinetics of hydrogen peroxide with copper and iron in seawater. Environ. Sci. Technol. 21, 804-810. Nerud, F., Baldrain, P., Gabriel, J. and Ogbeifun, D. (2001). Decolorization of synthetic dyes by the Fenton reagent and the Cu/pyridine/H2O2 system. Chemosphere 44, 957-961. Nunn, C. C., Schechter, R. S. and Wade, W. H. (1982). Visual evidence regarding the nature of hemimicelles through surface solubilization of pinacyanol chloride. J. Phys. Chem. 86, 3271-3272. Panda, A. K. and Chakraborty, A. K. (1997). Studies on the interaction of bacterial lipopolysaccharide with cationic dyes by absorbance and fluorescence spectroscopy. J. Photochemistry and Photobiology A: Chemistry 111, 157-162. Park, C. and Raines, R. T. (2001). Quantitative Analysis of the Effect of Salt Concentration on Enzymatic Catalysis. J. Am. Chem. Soc. 123, 11472-11479. Pecci, L., Montefoschi, G. and Cavallini, D. (1997). Some new details of the copper-hydrogen peroxide interaction. Biochemical and Biophysical Research Communications 235, 264-267. Pelmenschikov, V. and Siegbahn, P. E. M. (2005). Copper-zinc superoxide dismutase: Theoretical insights into the catalytic mechanism. Inorganic Chmistry 44, 3311-3320. Perez-Benito, J. F. (2004). Reaction pathways in the decomposition of hydrogen peroxide catalyzed by copper(II). Journal of Inorganic Biochemistry 98, 430-438. Robbins, M. H. and Drago, R. S. (1997). Activation of hydrogen peroxide for oxidation by copper(II) complexes. J. Catalysis 170, 295-303. Rorabacher, D. B. (2004). Electron Transfer by Copper Centers. Chem. Rev. 104, 651-697. Sabate, R., Gallardo, M. and Estelrich, J. (2001). Location of pinacyanol in micellar solutions of n-alkyl trimethylammonium bromide surfactants. Journal of Colloid and Interface Science 233, 205-210. Sabate, R., Gallardo, M., Maza, A. d. l. and Estelrich, J. (2001). A Spectroscopy Study of the Interaction of Pinacyanol with n-dodecyltrimethylammonium Bromide Micelles. Langmuir 17, 6433-6437. Sabate´, R. and Estelrich, J. (2003). Pinacyanol as effective probe of fibrillar beta-Amyloid peptide: Comparative study with congo red. Biopolymers (Biospectroscopy) 72, 455-463. Salem, I. A. and El-Maazawi, M. S. (2000). Kinetics and mechanism of color removal of methylene blue with hydrogen peroxide catalyzed by some supported alumina surfaces. Chemosphere 41, 1173-1180. Salem, M. A., Salem, I. A. and Gemeay, A. H. (1994). Kinetics and mechanism of H2O2 decomposition by Cu(II)-,Co(II)-,Fe(III)-amine complexes on the surface of silica-alumina (25% Al2O3). International Journal of Chemical Kinetics 26, 1055-1061. Segal, S. R. and Suib, S. L. (1997). Decomposition of pinacyanol chloride dye using several manganese oxide catalysts. Chem. Mater. 9, 2526-2532. Shah, V., Verma, P., Stopka, P., Gabriel, J., Baldrian, P. and Nerud, F. (2003). Decolorization of dyes with copper(II)/organic acid/hydrogen peroxide systems. Applied Catalysis B: Environmental 46, 287-292. Smith, A. E., Martell, R. M. and Motekaitis, R. J. (1995). NIST critically selected stability constants of metal complexes database, ver. 4.0. NIST Standard Reference Database 46. Stiff, M. J. (1971). Water Research 5, 585-599. Stone, D. L., Smith, D. K. and Whitwood, A. C. (2004). Copper amino-acid complexes - towards encapsulated metal centres. Polyhedron 23, 1709-1707. Sykora, J. (1997). Photochemistry of copper complexes and their environment aspects. Coor. Chem. Rev 159, 95-108. Verma, P., Baldrian, P. and Nerud, F. (2003). Decolorization of structurally different synthetic dyes using cobalt(II)/ascorbic acid/hydrogen peroxide system. Chemosphere 50, 975-979. Ueda, J.-I., Ozawa, T., Miyazaki, M. and Fujiwara, Y. (1994) Activation of hydrogen peroxide by copper(II) complexes with some Histidine-containing peptides and their SOD-like activities. Journal of Inorganic Biochemistry 55, 123-130. Verma, P., Shah, V., Baldrian, P., Gabriel, J., Stopka, P., Trnka, T. and Nerud, F. (2004). Decolorization of synthetic dyes using a copper complex with glucaric acid. Chemosphere 54, 291-295. 林景方, (2004) Electrochemical investigations of copper/amino-acid complexes by cycle voltammetry. 許朝昇, (2003). Experimental determination of copper(I) quantum yield for copper(II)-amino acid complexes in aqueous solution.;; (2006)

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碩士 ; 國立清華大學 ; 生醫工程與環境科學系 ; GH000934515 ; 本研究利用Cu(II)與20種自然胺基酸與β-Ala 形成的銅錯合物，於25°C的磷酸鹽溶液中活化過氧化氫，並偵測反應中2-甲喹啉藍(QB)的初始氧化速率來探討銅錯合物活化過氧化氫效率。爲了確認銅物種的影響，實驗中探討許多參數:pH、離子強度、溫度以及Cu(II)、胺基酸和過氧化氫的濃度。QB的氧化速率隨銅胺基酸錯合物濃度成一級反應，隨過氧化氫濃度成多級反應，這符合Michaelis-Menten動力方程式的描述。在20種胺基酸與β-Ala中，Cu-His錯合物有最強的活性。不同胺基酸的催化活性差異可達500倍，而此差異可能是由於胺基酸的結構與官能基影響過氧錯合物的形成。由實驗中發現1:1結合的銅胺基酸錯合物(CuL)是主要的活性催化物。最後藉由一價銅與兩價銅錯合物的實驗結果以及產物分析，推導出過氧化氫活化的反應機制。 ; Activation of hydrogen peroxide by Cu(II) complexes of 20 native amino acids (L) and β-Ala has been studied by measuring the initial oxidation rate of quinaldine blue(QB) in aqueous phosphate media at 25°C. System parameters such as pH, ionic strength, temperature and concentrations of Cu(II), amino acids, and hydrogen peroxide are examined to characterize the effects of Cu(II) speciation. The oxidation rate of QB is first order in Cu(II)-amino acid complexes and variable order in hydrogen peroxide, which can be explained in terms of Michaelis-Menten kinetics. Among 20 native amino acids and β-Ala, Cu(II)-histidine complex could more easily activate hydrogen peroxide than any other Cu(II)-amino acid complexes. The catalytic activities vary by about 500-fold and are discussed in terms of the ligand structure and function group, which affects the formation of lignad-Cu(II)-peroxide complexes. The catalytic activities of Cu(II) complexes with all 20 amino acids demonstrate that the 1:1 Cu(II) complexes (CuL) are the dominant species forming the active copper complex catalyst. Based on the experimental results of Cu(I) and Cu(II) complex systems and product measurement, a peroxide activation mechanism is proposed .

Titel:	銅-胺基酸錯合物活化H2O2之動力學與反應機制探討 ; Kinetics and mechanism of activation of hydrogen peroxide by copper(II) amino acid complexes
Autor/in / Beteiligte Person:	郭俊廷 ; Kuo, Chun-Ting ; 吳劍侯 ; Wu, Chien-Hou
Link:	http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/35367
Quelle:	Ahner, B. A., Lee, J. G., Price, N. M. and Morel, F. M. M. (1998). Phytochelatin concentration in the equatorial Pacific. Deep-Sea Res. I 45, 1779-1796. Akagawa, M. and Suyama, K. (2002). Oxidative deamination by hydrogen peroxide in the presence of metals. Free Radical Research, 36, 13-21. Ali, F. E., Barnham, K. J., Barrow, C. J. and Separovic, F. (2004). Metal catalyzed oxidation of tyrosine residues by different oxidation systems of copper/hydrogen peroxide. Journal of Inorganic Biochemistry 98, 173-184. Baldrian, P., Cajthaml, T., Merhautova, V., Gabriel, J., Nerud, F., Stopka, P., Hruby, M. and Benes, M. J. (2005). Degradation of polycyclic aromatic hydrocarbons by hydrogen peroxide catalyzed by heterogeneous polymeric metal chelates. Applied Catalysis B: Environmental 59, 267-274. Benedito, F. L., Nakagaki, S., Saczk, A. A., Peralta-Zamora, P. G. and Costa, C. M. M. (2003). Study of metalloporphyrin covalently bound to silica as catalyst in the ortho-dianisidine oxidation. Applied Catalysis A 250, 1-11. Cai, R., Kubota, Y. and Fujishima, A. (2003). Effect of copper ions on the formation of hydrogen peroxide from photocatalytic titanium dioxide particles. J. Catalysis 219, 214-218. Chen, L.-H., Liu, L.-Z. and Shen, H.-X. (2003). Mn(II)-sodium dodecyl sulphate complex mimic enzyme-catalyzed fluorescence quenching of Pyronine B by hydrogen peroxide. Analytica Chimica Acta 480, 143-150. EL-Gahami, M. A., Khafagy, Z. A., Ali, A. M. M. and Ismail, N. M. (2004). Thermal, spectroscopic, cyclic voltammetric, and biological activity studies of cobalt(II), nickel(II), and copper(II) complexes of dicarboxylic amino acids and 8-hydroxyquinoline. Journal of Inorganic and Organometallic Polymers 14, 117-129. Fayolle, M. and Romagna, F. (1997). Copper CMP evaluation: planarization issues. Microelectronic Engineering 37/38, 135-141. Felmy, A. R., Girvin, D. C. and Jenne, E. A. (1984). A computer program for calculating aqueous geochemical equilibria. U. S. Environmental Protect Agency, Athens, GA, EPA-600/3-84-032. Gabriel, J., Baldrian, P., Verma, P., Cajthaml, T., Merhautová, V., Eichlerová, I., Stoytchev, I., Trnka, T., Stopka, P. and Nerud, F. (2004). Degradation of BTEX and PAHs by Co(II) and Cu(II)-based radical-generating systems. Applied Catalysis B: Environmental 51, 159-164. Gorantla, V. R. K., Matijevic, E. and Babu, S. V. (2005). Amino acids as complexing agents in chemical-mechanical planarization of copper. Chem. Mater. 17, 2076-2080. Hariharaputhiran, M., Zhang, J., Ramarajan, S., Keleher, J. J. and Li, Y. (2000). Hydroxyl radical formation in H2O2-amino acid mixtures and chemical mechanical polishing of copper. J. Electrochem. Soc. 147, 3820-3826. Hayase, K. and Zeep, R. G. (1991). Photolysis of copper(II)-amino acid complexes in water. Environ. Sci. Technol. 25, 1273-1279. Kato, Y., Kitamoto, N., Kawai, Y. and Osawa, T. (2001). The hydrogen peroxide/copper ion system, but not other metal-catalyzed oxidation systems, produces protein-bound dityrosine. Free Radical Biology & Medicine, 31, 624-632. Lapenna, D., Ciofani, G., Pierdomenico, S. D., Giamberardino, M. A. and Cuccurullo, F. (2005). Copper, zinc superoxide dismutase plus hydrogen peroxide: a catalytic system for human lipoprotein oxidation. FEBS Letters 579, 245-250. Lekchiri, A., Brighli, M., Methenitis, C., Morcellet, J. and Morcellet, M. (1991). Complexation of a polyelectrolyte derived from glutamic acid with copper(II).Catalase-like activity of the complexes. Journal of Inorganic Biochemistry 44, 229-238. Lekchiri, A., Castellano, A., Morcelle, J. and Morcellet, M. (1991). Copper of complexes and catalyse-like activity a polyelectrolyte derived from aspartic acid. Eur. Polym. J. 27, 1271-1278. Lin, T.-Y. and Wu, C.-H. (2005). Activation of hydrogen peroxide in copper(II)/amino acid/H2O2 systems: effects of pH and copper speciation. Journal of Catalysis 232, 117-126. Meng, M.,Chane, T-L., Sun, Y-J. and Hsiao, C-D. (1999). Probing the location and function of the conserved histidine residue of phosphoglucose isomerase by using an active site directed inhibitor N-bromoacetylethanolamine phosphate. Protein Science 8, 2438-2443. Moffett, J. W. and Zika, R. G. (1987). Photochemistry of copper complexes in seawater. Environ. Aqua. Sys Chap9. Moffett, J. W. and Zika, R. G. (1987). Reaction kinetics of hydrogen peroxide with copper and iron in seawater. Environ. Sci. Technol. 21, 804-810. Nerud, F., Baldrain, P., Gabriel, J. and Ogbeifun, D. (2001). Decolorization of synthetic dyes by the Fenton reagent and the Cu/pyridine/H2O2 system. Chemosphere 44, 957-961. Nunn, C. C., Schechter, R. S. and Wade, W. H. (1982). Visual evidence regarding the nature of hemimicelles through surface solubilization of pinacyanol chloride. J. Phys. Chem. 86, 3271-3272. Panda, A. K. and Chakraborty, A. K. (1997). Studies on the interaction of bacterial lipopolysaccharide with cationic dyes by absorbance and fluorescence spectroscopy. J. Photochemistry and Photobiology A: Chemistry 111, 157-162. Park, C. and Raines, R. T. (2001). Quantitative Analysis of the Effect of Salt Concentration on Enzymatic Catalysis. J. Am. Chem. Soc. 123, 11472-11479. Pecci, L., Montefoschi, G. and Cavallini, D. (1997). Some new details of the copper-hydrogen peroxide interaction. Biochemical and Biophysical Research Communications 235, 264-267. Pelmenschikov, V. and Siegbahn, P. E. M. (2005). Copper-zinc superoxide dismutase: Theoretical insights into the catalytic mechanism. Inorganic Chmistry 44, 3311-3320. Perez-Benito, J. F. (2004). Reaction pathways in the decomposition of hydrogen peroxide catalyzed by copper(II). Journal of Inorganic Biochemistry 98, 430-438. Robbins, M. H. and Drago, R. S. (1997). Activation of hydrogen peroxide for oxidation by copper(II) complexes. J. Catalysis 170, 295-303. Rorabacher, D. B. (2004). Electron Transfer by Copper Centers. Chem. Rev. 104, 651-697. Sabate, R., Gallardo, M. and Estelrich, J. (2001). Location of pinacyanol in micellar solutions of n-alkyl trimethylammonium bromide surfactants. Journal of Colloid and Interface Science 233, 205-210. Sabate, R., Gallardo, M., Maza, A. d. l. and Estelrich, J. (2001). A Spectroscopy Study of the Interaction of Pinacyanol with n-dodecyltrimethylammonium Bromide Micelles. Langmuir 17, 6433-6437. Sabate´, R. and Estelrich, J. (2003). Pinacyanol as effective probe of fibrillar beta-Amyloid peptide: Comparative study with congo red. Biopolymers (Biospectroscopy) 72, 455-463. Salem, I. A. and El-Maazawi, M. S. (2000). Kinetics and mechanism of color removal of methylene blue with hydrogen peroxide catalyzed by some supported alumina surfaces. Chemosphere 41, 1173-1180. Salem, M. A., Salem, I. A. and Gemeay, A. H. (1994). Kinetics and mechanism of H2O2 decomposition by Cu(II)-,Co(II)-,Fe(III)-amine complexes on the surface of silica-alumina (25% Al2O3). International Journal of Chemical Kinetics 26, 1055-1061. Segal, S. R. and Suib, S. L. (1997). Decomposition of pinacyanol chloride dye using several manganese oxide catalysts. Chem. Mater. 9, 2526-2532. Shah, V., Verma, P., Stopka, P., Gabriel, J., Baldrian, P. and Nerud, F. (2003). Decolorization of dyes with copper(II)/organic acid/hydrogen peroxide systems. Applied Catalysis B: Environmental 46, 287-292. Smith, A. E., Martell, R. M. and Motekaitis, R. J. (1995). NIST critically selected stability constants of metal complexes database, ver. 4.0. NIST Standard Reference Database 46. Stiff, M. J. (1971). Water Research 5, 585-599. Stone, D. L., Smith, D. K. and Whitwood, A. C. (2004). Copper amino-acid complexes - towards encapsulated metal centres. Polyhedron 23, 1709-1707. Sykora, J. (1997). Photochemistry of copper complexes and their environment aspects. Coor. Chem. Rev 159, 95-108. Verma, P., Baldrian, P. and Nerud, F. (2003). Decolorization of structurally different synthetic dyes using cobalt(II)/ascorbic acid/hydrogen peroxide system. Chemosphere 50, 975-979. Ueda, J.-I., Ozawa, T., Miyazaki, M. and Fujiwara, Y. (1994) Activation of hydrogen peroxide by copper(II) complexes with some Histidine-containing peptides and their SOD-like activities. Journal of Inorganic Biochemistry 55, 123-130. Verma, P., Shah, V., Baldrian, P., Gabriel, J., Stopka, P., Trnka, T. and Nerud, F. (2004). Decolorization of synthetic dyes using a copper complex with glucaric acid. Chemosphere 54, 291-295. 林景方, (2004) Electrochemical investigations of copper/amino-acid complexes by cycle voltammetry. 許朝昇, (2003). Experimental determination of copper(I) quantum yield for copper(II)-amino acid complexes in aqueous solution.;; (2006)
Veröffentlichung:	2006
Medientyp:	unknown
Schlagwort:	銅胺基酸過氧化氫 copper amino acid H2O2 Time: 21
Sonstiges:	Nachgewiesen in: BASE Sprachen: Chinese Collection: National Tsing Hua University Institutional Repository (NTHUR) Document Type: other/unknown material File Description: 155 bytes; text/html Language: Chinese

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