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Steady-State and Time Resolved Fluorescence Analysis on Tyrosine–Histidine Model Compounds

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Abstract

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.

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Acknowledgments

This work was supported by CNRS, ULP and ANR. M. Voicescu is grateful for financial support from the CNRS. The authors are indebted to Prof. van der Donk’s team, UIUC, Illinois, USA for Tyr–His model compounds synthesis.

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Authors and Affiliations

  1. Laboratoire de Spectroscopie Vibrationnelle et Electrochimie des Biomolécules, UMR 7177, Institut de Chimie, CNRS-Université Louis Pasteur, 1 rue Blaise Pascal, 67070, Strasbourg, France

    Mariana Voicescu, Martine Heinrich & Petra Hellwig

  2. Romanian Academy, Institute of Physical Chemistry “Ilie Murgulescu”, Splaiul Independentei 202, 060021, Bucharest, Romania

    Mariana Voicescu

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  1. Mariana Voicescu
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  2. Martine Heinrich
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  3. Petra Hellwig
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Correspondence to Mariana Voicescu.

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Voicescu, M., Heinrich, M. & Hellwig, P. Steady-State and Time Resolved Fluorescence Analysis on Tyrosine–Histidine Model Compounds. J Fluoresc 19, 257–266 (2009). https://doi.org/10.1007/s10895-008-0411-5

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  • DOI: https://doi.org/10.1007/s10895-008-0411-5

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