| Автор | Jameson, Guy N. L. |
| Автор | Linert, Wolfgang |
| Дата выпуска | 2001 |
| dc.description | The kinetics of the oxidation of 6-hydroxydopamine [5-(2-aminoethyl)benzene-1,2,4-triol, protonated form H3LH<sup>+</sup>] by iron(III) under anaerobic conditions are presented. A complex mechanism whereby the o- (oQ), p- (pQ), and triketo-quinones (tQ) are formed via parallel inner- and outer-sphere electron transfer mechanisms has been established. The outer-sphere mechanism is particularly fast (nearly diffusion limiting) and predominates. By following the dependence of the rate on ionic strength it has been shown that a deprotonated form of 6-hydroxydopamine reacts via an outer-sphere reaction with all species of iron. Like the other catecholamines [3,4-dihydroxy-1-(2-aminoethyl)benzenes], but to a much smaller extent, complex formation occurs by FeOH<sup>2+</sup> reacting with the fully protonated form of 6-hydroxydopamine. Three different semiquinones are initially produced; two of them, the triketo- and p-semiquinones, are tautomers. The o- and triketo-semiquinones react quickly with another iron atom to form their respective quinones. The p-semiquinone, however, is seemingly stable, partly reacting with more iron and partly disproportionating to form pQ and reforming 6-hydroxydopamine. At pHs above 2.5, pQ and oQ are in equilibrium via a deprotonated quinone Q<sup>â </sup>. The biological implications of this mechanism are discussed. |
| Формат | application.pdf |
| Издатель | Royal Society of Chemistry |
| Название | The oxidation of 6-hydroxydopamine in aqueous solution. Part 3.12 Kinetics and mechanism of the oxidation with iron(III)â Rate constants and absorbance data are available as supplementary data. For direct electronic access see http://www.rsc.org/suppdata/p2/b0/b007203f/ |
| Тип | ART |
| Журнал | Journal of the Chemical Society, Perkin Transactions 2 |
| Первая страница | 569 |
| Последняя страница | 575 |
| Аффилиация | Jameson Guy N. L.; Institute of Inorganic Chemistry, Technical University of Vienna |
| Аффилиация | Linert Wolfgang; Institute of Inorganic Chemistry, Technical University of Vienna |
| Выпуск | 4 |
| Библиографическая ссылка | W. Linert, E. Herlinger, R. F. Jameson, E. Kienzl, K. Jellinger, M. B. H. Youdim, Biochem. Biophys. Acta, 1996, 1316, 160 |
| Библиографическая ссылка | U. El-Ayaan, E. Herlinger, R. F. Jameson, W. Linert, J. Chem. Soc., Dalton Trans., 1997, 2813 |
| Библиографическая ссылка | W. Linert, R. F. Jameson, E. Herlinger, W. Linert, E. Herlinger, R. F. Jameson, Inorg. Chim. Acta, 1991, 187, 239, J. Chem. Soc., Perkin Trans. 2, 1993, 2435 |
| Библиографическая ссылка | U. El-Ayaan, R. F. Jameson, W. Linert, J. Chem. Soc., Dalton Trans., 1998, 1315 |
| Библиографическая ссылка | J. K. Dohrmann, B. Bergmann, A. E. AlegrÃa, M. López, N. Guevara, V. A. Roginsky, L. M. Pisarenko, W. Bors, C. Michel, M. Saran, V. A. Roginsky, L. M. Pisarenko, W. Bors, C. Michel, J. Phys. Chem., 1995, 99, 1218, J. Chem. Soc., Faraday Trans., 1996, 92, 4965, J. Chem. Soc., Faraday Trans., 1998, 94, 13, 1835, J. Chem. Soc., Perkin Trans. 2, 1999, 871 |
| Библиографическая ссылка | J.-Y. Chien, J. Am. Chem. Soc., 1948, 70, 2256 |
| Библиографическая ссылка | R. G. Pearson, L. C. King, S. H. Langer, J. Am. Chem. Soc., 1951, 73, 4149 |
