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Issue 6, 2013
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Light-induced tryptophan radical generation in a click modular assembly of a sensitiser-tryptophan residue

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Abstract

Click chemistry was used as an efficient method to covalently attach a chromophore to an amino acid. Such easily prepared model systems allow for time-resolved studies of one-electron oxidation reactions by the excitation of the chromophore by a laser flash. The model complex ruthenium–tryptophan (Ru–Trp) has been synthesised and studied for its photophysical and electrochemical properties. Despite a small driving force of less than 100 meV, excitation with a laser flash results in fast internal electron transfer leading to the formation of the protonated radical (Trp˙H+). At neutral pH electron transfer is followed by deprotonation to form the neutral Trp˙ radical with the rate depending on the concentration of water acting as the proton acceptor. The formation of the tryptophan radical was confirmed by EPR.

Graphical abstract: Light-induced tryptophan radical generation in a click modular assembly of a sensitiser-tryptophan residue

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Publication details

The article was received on 23 Jan 2013, accepted on 15 Mar 2013 and first published on 18 Mar 2013


Article type: Paper
DOI: 10.1039/C3PP50021G
Citation: Photochem. Photobiol. Sci., 2013,12, 1074-1078
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    Light-induced tryptophan radical generation in a click modular assembly of a sensitiser-tryptophan residue

    S. Sheth, A. Baron, C. Herrero, B. Vauzeilles, A. Aukauloo and W. Leibl, Photochem. Photobiol. Sci., 2013, 12, 1074
    DOI: 10.1039/C3PP50021G

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