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Effect of Amino Group Charge on the Photooxidation Kinetics of Aromatic Amino Acids

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International Tomography Center, Institutskaya 3a, 630090 Novosibirsk, Russia
Novosibirsk State University, Pirogova 2, 630090 Novosibirsk, Russia
§ Institute of Physical and Theoretical Chemistry, Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria
*A. V. Yurkovskaya: tel, +7 383 3331333; fax, +7 383 3331399; e-mail, [email protected]
Cite this: J. Phys. Chem. A 2014, 118, 2, 339–349
Publication Date (Web):December 19, 2013
https://doi.org/10.1021/jp4097919
Copyright © 2013 American Chemical Society

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    Abstract

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    The kinetics of the photooxidation of aromatic amino acids histidine (His), tyrosine (Tyr), and tryptophan (Trp) by 3,3′,4,4′-benzophenonetetracarboxylic acid (TCBP) has been investigated in aqueous solutions using time-resolved laser flash photolysis and time-resolved chemically induced dynamic nuclear polarization. The pH dependence of quenching rate constants is measured within a large pH range. The chemical reactivities of free His, Trp, and Tyr and of their acetylated derivatives, N-AcHis, N-AcTyr, and N-AcTrp, toward TCBP triplets are compared to reveal the influence of amino group charge on the oxidation of aromatic amino acids. The bimolecular rate constants of quenching reactions between the triplet-excited TCBP in the fully deprotonated state and tryptophan, histidine, and tyrosine with a positively charged amino group are kq = 2.2 × 109 M–1 s–1 (4.9 < pH < 9.4), kq = 1.6 × 109 M–1 s–1 (6.0 < pH < 9.2), and kq = 1.5 × 109 M–1 s–1 (4.9 < pH < 9.0), respectively. Tryptophan, histidine, and tyrosine with a neutral amino group quench the TCBP triplets with the corresponding rate constants kq = 8.0 × 108 M–1 s–1 (pH > 9.4), kq = 3.0 × 108 M–1 s–1 (pH > 9.2), and kq = (4.0–10.0) × 108 M–1 s–1 (9.0 < pH < 10.1) that are close to those for the N-acetylated derivatives. Thus, it has been established that the presence of charged amino group changes oxidation rates by a significant factor; i.e., His with a positively charged amino group quenches the TCBP triplets 5 times more effectively than N-AcHis and His with a neutral amino group. The efficiency of quenching reaction between the TCBP triplets and Tyr and Trp with a positively charged amino group is about 3 times as high as that of both Tyr and Trp with a neutral amino group, N-AcTyr and N-AcTrp.

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    125 MHz 13C NMR of 3,3′,4,4′-benzophenonetetracarboxylic acid. 200 MHz 1H spectra of 3,3′,4,4′-benzophenonetetracarboxylic acid, l-phenylalanine-l-histidine, l-histidine-l-phenylalanine, and l-histidine-l-histidine. Chemical shift titration curves of 3,3′,4,4′-benzophenonetetracarboxylic acid, l-histidine-l-phenylalanine, l-phenylalanine-l-histidine, and l-histidine-l-histidine. 200 MHz 1H CIDNP spectra of l-histidine-l-phenylalanine, l-phenylalanine-l-histidine, and l-histidine-l-histidine. This information is available free of charge via the Internet at http://pubs.acs.org.

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