Steady-state and time resolved fluorescence analysis on tyrosine-histidine model compounds

Four model compounds, for a tyrosine-histidine covalent bonding, 2-(5-imidazolyl)-4-methylphenol (C-C bonding in ortho-position at the phenyl group); 2'-(1-imidazolyl)-4-methylphenol (C-N bonding in ortho'-position at the phenyl group); 2-(5-imidazolyl)-4-H-phenol and 2-(5-imidazolyl)-4-H-phenol, at physiological pH have been studied by UV-Vis absorption, steady-state and time resolved fluorescence spectroscopy. Their absorption and emission properties are presented and discussed. The photophysical properties depend on the para-substituted phenyl group as well as on C-C/C-N bonding in the Phenol-Imidazole linkage. The N position, N1-N3/N1-N4, in the imidazole group was found to be relevant. The results are discussed with relevance to the redox processes of tyrosine and to better understand the role of a tyrosine-histidine covalent linkage as found in cytochrome c oxidase.