Synthetic Models for Heme Proteins
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- Kilian Huber
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1 Diss. ETH No Synthetic Models for Heme Proteins A dissertation submitted to the ETHZURICH for the degree of DOCTOR OF SCIENCES Presented by Henry Dube Dipl, Chem. LMU Munich born April 24, 1978 citizen of the Federa1 Republic of Germany accepted on the recommendation of Prof. Dr. Franccis Diederich. examiner Prof. Dr. Bernhard Jaun, co-examiner Prof. Dr. Gunnar Jeschke, co-examiner Zurich 2008
2 Summary Summary In the first part of this work it was attempted to find a direct evidence for a hydrogen bond interaction between bound dioxygen and a distal hydrogen bond donor in a synthetic model system for Mb and Rb. shown below. The model systems that were explored are EtO,C? EtO,C? 4-Ca S-Ca CW EPR and Puls EPR spcctra of the cobalt complexes were measured and analyzed by Dr. Carlos Calle y Richter and Besnik Kasumaj in the group of Prof Dr. Arthur Schweiger in the Laboratory of Physical Chemistry at the ETH Zurich. Q band Davies-ENDOR spectroscopy was used to determine thc proton hyperfinecouplings of the radical dioxygen adducts l-co-0 2 to 3-Co-0 2 and 5-Co-0 2. Only for the dioxygen adduct of 1-Co a large hyperfine splitting was observed. This hyperfine splitting disappcared in the corresponding spectra of the same complex after deuterium exchange of the only exchangeable proton at the distal benzimidazole. Simulations of the large hypefine splitting in 1-Co-0 2 revealed that the hydrogen bond is mainly dipolar in nature and the interacting exchangeable proton is positioned directly above bound dioxygen in 2.3 A distance. v
3 Summary The study was completed with the examination of the hyperfine splittings in Co-Mb-02 with the same EPR method. CW EPR and Puls EPR spectra of Co-Mb and Co~Mb-02 were measured and analyzed by Besnik Kasumaj in the Laboratory of Physical Chemistry at the ETH Zurich under supervision of Prof Dr. Gunnar Jeschke. An even larger hyperfine splitting, up to 19.0 MHz in magnitude, was found in the corresponding frozen-solution Q-band Oavies-ENOOR spectra of Co-Mb-02 (13 K). Upon 0 20 exchange of the buffer solution, this large hyperfine splitting disappeared, Like in our model compound, also in Co-Mb-02 a defined distal hydrogen bond was detected. The evolution of the largest and exchangeabje proton hyperfine splitting over the different field positions in Co-Mb-02is the same as in the model complex l-co-02, only its magnitude is greater in the pro tein, suggesting a similar orientation of the two hydrogen bonds but a eioser distance (2.0 Ä) of the interacting proton in Co-Mb-02. Also similar to our model complex l-co-02, the character of the hydrogen bond in Co-Mb-02 is mainly dipojar in nature. Thus, we could show that model complex l-co-02is an excellent model for the natural proteins Mb and Hb, which reproduces well crucial properties of the natural proteins. In the second part of this work a new model compound far cytochrorne c, 64-Fe, was investigated. 64-Zn The redox potential of compound 64-Fe was measured in CH2Ch in order to compare it to the redox potentials of the series of model compounds for cytochrome b5 and to cyrochrome c itself. Cyc1ic voltammetry was measured by Florian Puschmann and Matthias Vogt in the group ofprof Dr. Hansjorg Grützmacher in the Laboratory of Inorganic Chemistry at the ETH Zurich. VI
4 Summary Upon addition of ferroeene as internal reference, the eyclie voltammogramm of 64-Fe eould not be resolved clearly. Assuming that the most pronouneed reduetion peak in the eyclie voltammogramm including ferroeene is identieal with the respeetive peak in the voltammogramm obtained without ferroeene, the redox potential of 64-Fe would be 0.17 V vs. SCE eompared to 0.00 V for eytoehrome c vs. SCE. The redox potential of 64-Fe is more than 0.37 V positively shifted eompared to the similar eompound bearing two imidazole ligands instead of one thioether and one imidazole. A similar positive shift of the redox potential is also seen when eomparing the natural cytochromes 175 (-0.24 V vs. SCE) and eytoehrome c (0.06 V vs. SCE). VII
5 Zusammenfassung Zusammenfassung Im ersten Teil dieser Arbeit wurde versucht, einen direkten Beweis für eine distale Wasserstoffbrücke zu gebundenem Disauerstoff in einem Modellsystem für Mb und Hb zu finden. Die hierzu untersuchten Modellsysteme sind unten gezeigt. 1-Co 4-Co CW-EPR- und Puls-EPR-Spektren wurden von Dr. Carlos Calle y Richter und Besnik Kasumaj in der Gruppe von Prof Dr. Arthur Schweiger im Laboratorium für Physikalische Chemie an der ETH Zürich gemessen und analysiert. Die Protonenhyperfeinkopplungen der radikalischen Disauerstoffaddukte l-co-0 2 bis 3 Co-0 2 und 5-Co-0 2 wurden mittels Q-Band-Davies-ENDOR-Spektroskopie untersucht. Für l-co-0 2 wurde eine sehr grosse Hyperfeinwechselwirkung gemessen, die nach Austausch des distalen Benzimidazolprotons durch D 20 verschwand. Simulationcn dieser Hyperfeinwechselwirkung in 1-Co-0 2 zeigten, dass die gemessene Wasserstoffbrücke hauptsächlich dipolarer Natur ist und dass das wechselwirkende Proton in einem Abstand von 2.3 A über dem gebundenen Disauerstoff steht. Nachfolgend wurden die Protonenhyperfeinkopplungen von natürlichem Co Mb-0 2 mit derselben EPR Methode gemessen. CW-EPR- und Puls-EPR-Spektren VIII
6 Zusammenfassung wurden von Besnik Kasumaj unter Betreuung von Prof Dr. Gunnar Jeschke im Laboratorium für Physikalische Chemie an der ETH Zürich gemessen und analysiert. Im Protein konnte eine noch grössere Hyperfcinwechselwirkung, die bis zu 19.0 MHz reichte, gemessen werden. Nach D 20-Austausch der Pufferlösung verschwand diese grösste Kopplung. Ebenso wie in unserer Modellverbindung wurde auch in Co-Mb O2 eine distale Wasserstoffbrücke gemessen. Die spektrale Entwicklung dieser Wechselwirkung an verschiedenen Feldpositionen entspricht dabei genau derjenigen unseres Modellkomplexes l-co-02, lediglich das Ausmass der Kopplung ist grösser im Protein, was auf einen kürzeren Abstand (2.0 A) des interagierenden distalen Protons III Co-Mb-02 zurückzuführen ist. Ebenfalls analog zu unserer Modellverbindung ist die hauptsächlich dipolare Natur der Wasserstoffbrücke im Protein. Daher kann der Komplex I-Co als sehr gutes Modell für die natürlichen Proteine Mb und Hb angesehen werden. Im zweiten Teil dieser Arbeit wurde das neuartiges Modell für Cytochrom c, 64-Fe, untersucht. ss-zn Das Redoxpotential von Verbindung 64-Fe wurde in CH 2Ch gemessen um es mit den Potentialen einer Serie von Modellverbindungen für Cytochrom 65 und Cytochrorn c selbst zu vergleichen. CyclovoItammogramme wurden von Florian Puschmann und Matthias Vogt in der Gruppe von Prof Dr. Hansjörg Grützmacher im Laboratorium für Anorganische Chemie an der ETE Zürich gemessen. Nach Zugabe von Ferrocen als interne Referenz konnte das Cyclovoltammogramm von 64 Fe nicht mehr klar aufgelöst werden. Unter der Annahme, dass das ausgeprägteste Spitzenpotential im Cyclovoltammogramm mit Ferrocen identisch mit dem IX
7 Zusammenfassung Spitzenpotential im Cyclovoltammogramm ohne Ferrocen ist, wurde das Redoxpotential von 64-Fe mit 0.17 V vs. SCE bestimmt. Natürliches Cytochrom c hat ein Potential von 0.00 V vs. SCE. Das Redoxpotential von 64-Fe ist gegenüber der gleichartigen Verbindung mit zwei Imidazolliganden mehr als 0.37 V positiv verschoben. Eine ähnliche Positivverschiebung erhält man, wenn man das Redoxpotential von natürlichem Cytochrom b5 (-0.24 V vs. SCE) mit demjenigen von Cytochrom c (0.06 V vs. SCE) vergleicht. x
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