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J. Biol. Chem., Vol. 266, Issue 26, 17201-17211, Sep, 1991
ER Stadtman and BS Berlett
The oxidation of amino acids by Fenton reagent (H2O2 + Fe(II] leads mainly
to the formation of NH+4, alpha-ketoacids, CO2, oximes, and aldehydes or
carboxylic acids containing one less carbon atom. Oxidation is almost
completely dependent on the presence of bicarbonate ion and is stimulated
by iron chelators at levels which are substoichiometric with respect to the
iron concentration but is inhibited at higher concentrations. The
stimulatory effect of chelators is not due merely to solubilization of
catalytically inactive polymeric forms of Fe(OH)3 nor to the conversion of
Fe(II) to complexes incapable of scavenging hydroxyl radicals. The results
suggest that an iron chelate and another as yet unidentified form of iron
are both required for maximal rates of amino acid oxidation. The metal
ion-catalyzed oxidation of amino acids is likely a "caged" process, since
the oxidation is not inhibited by hydroxyl radical scavengers, and the
relative rates of oxidation of various amino acids by the Fenton system as
well as the distribution of products formed (especially products of
aromatic amino acids) are significantly different from those reported for
amino acid oxidation by ionizing radiation. Several iron-binding proteins,
peptides, and hemoglobin degradation products can replace Fe(II) or Fe(III)
in the bicarbonate-dependent oxidation of amino acids. In view of their
ability to sequester metal ions and their susceptibility to oxidation by
H2O2 in the presence of physiological concentrations of bicarbonate, amino
acids may serve an important role in antioxidant defense against tissue
damage.
Fenton chemistry. Amino acid oxidation
Laboratory of Biochemistry, National Heart, Lung, and Blood Institute, National Institutes of Health, Bethesda, Maryland 20892.
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