Oxidative deamination by hydrogen peroxide in the presence of metals.
Various amines, including lysine residue of bovine serum albumin, were oxidatively deaminated to form the corresponding aldehydes by a H2O2/Cu2+ oxidation system at physiological pH and temperature. The resulting aldehydes were measured by high-performance liquid chromatography. We investigated the effects of metal ions, pH, inhibitors, and O2 on the oxidative deamination of benzylamine by H202. The formation of benzaldehyde was the greatest with Cu2+, and catalysis occurred with Co2+, VO2+, and Fe3+. The reaction was greatly accelerated as the pH value rose and was markedly inhibited by EDTA and catalase. Dimethyl sulfoxide and thiourea, which are hydroxyl radical scavengers, were also effective in inhibiting the generation of benzaldehyde, indicating that the reaction is a hydroxyl radical-mediated reaction. Superoxide dismutase greatly stimulated the reaction, probably due to the formation of hydroxyl radicals. O2 was not required in the oxidation, and instead slightly inhibited the reaction. We also examined several oxidation systems. Ascorbic acid/O2/Cu2+ and hemoglobin/H2O2 systems also converted benzylamine to benzaldehyde. The proposed mechanism of the oxidative deamination by H2O2/Cu2+ system is discussed.
Akagawa
Mitsugu
M
Department of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Suyama
Kyozo
K
D001547:Benzaldehydes / Q000494:pharmacology; D001596:Benzylamines / Q000494:pharmacology; D002374:Catalase / Q000378:metabolism / Q000494:pharmacology; D002384:Catalysis; D003035:Cobalt / Q000494:pharmacology; D003300:Copper / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D004492:Edetic Acid / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000494:pharmacology; D005609:Free Radicals; D006861:Hydrogen Peroxide / Q000494:pharmacology*; D006863:Hydrogen-Ion Concentration; D007477:Ions; D007501:Iron / Q000494:pharmacology; D008239:Lysine / Q000737:chemistry; D008670:Metals / Q000494:pharmacology*; D008956:Models, Chemical; D018384:Oxidative Stress; D010100:Oxygen / Q000378:metabolism* / Q000494:pharmacology; D013482:Superoxide Dismutase / Q000378:metabolism; D013997:Time Factors; D014638:Vanadates / Q000494:pharmacology
D001547:Benzaldehydes; D001596:Benzylamines; D016166:Free Radical Scavengers; D005609:Free Radicals; D007477:Ions; D008670:Metals; D003035:Cobalt; D014638:Vanadates; D003300:Copper; D004492:Edetic Acid; C030796:benzylamine; D006861:Hydrogen Peroxide; D007501:Iron; D002374:Catalase; D013482:Superoxide Dismutase; D008239:Lysine; D010100:Oxygen; C032175:benzaldehyde