Mechanism and stoichiometry of 2,2-diphenyl-1-picrylhydrazyl radical scavenging by glutathione and its novel alpha-glutamyl derivative. Viirlaid, S., Mahlapuu, R., Kilk, K., Kuznetsov, A., Soomets, U., & Järv, J. Bioorganic chemistry, 37(4):126-32, 2009. Website abstract bibtex Kinetic mechanism and stoichiometry of scavenging the 2,2-diphenyl-1-picrylhydrazyl radical by glutathione and its novel analog, containing alpha-glutamyl residue in place of the gamma-glutamyl moiety, were studied using different ratios of reagents. At low concentrations of the peptides, the process was described as a bimolecular reaction obeying the stoichiometric ratio 1:1. However, at excess of peptides the formation of a non-covalent complex between the reagents was discovered and characterized by dissociation constants K = 0.61 mM for glutathione and K = 0.27 mM for the glutathione alpha-glutamyl analog, respectively. The complex formation was followed by a reaction step that was characterized by the similar rate constant k = 0.02 s(-1) for both peptides. Thus, the apparently different antioxidant activity of these two peptides, observed under common assay conditions, was determined by differences in the formation of this non-covalent complex.
@article{
title = {Mechanism and stoichiometry of 2,2-diphenyl-1-picrylhydrazyl radical scavenging by glutathione and its novel alpha-glutamyl derivative.},
type = {article},
year = {2009},
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keywords = {Biphenyl Compounds,Biphenyl Compounds: chemistry,Free Radical Scavengers,Free Radical Scavengers: chemistry,Free Radical Scavengers: metabolism,Glutathione,Glutathione: analogs & derivatives,Glutathione: chemistry,Glutathione: metabolism,Indicators and Reagents,Indicators and Reagents: chemistry,Kinetics,Peptides,Peptides: chemical synthesis,Peptides: chemistry,Picrates,Picrates: chemistry},
pages = {126-32},
volume = {37},
websites = {http://www.sciencedirect.com/science/article/pii/S0045206809000224},
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abstract = {Kinetic mechanism and stoichiometry of scavenging the 2,2-diphenyl-1-picrylhydrazyl radical by glutathione and its novel analog, containing alpha-glutamyl residue in place of the gamma-glutamyl moiety, were studied using different ratios of reagents. At low concentrations of the peptides, the process was described as a bimolecular reaction obeying the stoichiometric ratio 1:1. However, at excess of peptides the formation of a non-covalent complex between the reagents was discovered and characterized by dissociation constants K = 0.61 mM for glutathione and K = 0.27 mM for the glutathione alpha-glutamyl analog, respectively. The complex formation was followed by a reaction step that was characterized by the similar rate constant k = 0.02 s(-1) for both peptides. Thus, the apparently different antioxidant activity of these two peptides, observed under common assay conditions, was determined by differences in the formation of this non-covalent complex.},
bibtype = {article},
author = {Viirlaid, Säde and Mahlapuu, Riina and Kilk, Kalle and Kuznetsov, Aleksei and Soomets, Ursel and Järv, Jaak},
journal = {Bioorganic chemistry},
number = {4}
}
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