Oxidative deamination of benzylamine by glycoxidation.
In the present study, model reactions for the oxidative deamination by glycoxidation using benzylamine were undertaken to elucidate the detail of the reaction. Glucose, 3-deoxyglucosone (3-DG), and methylglyoxal (MG) oxidatively deaminated benzylamine to benzaldehyde in the presence of Cu(2+) at a physiological pH and temperature but not glyoxal. 3-DG and MG were more effective oxidants than glucose. We have determined the effects of metal ions, pH, oxygen, and radical scavengers on the oxidative deamination. The formation of benzaldehyde was greatest with Cu(2+), and was accelerated at a higher pH and in the presence of oxygen. EDTA, catalase, and dimethyl sulfoxide significantly inhibited the oxidation, suggesting the participation of reactive oxygen species. From these results, we propose a mechanism for the oxidative deamination by the Strecker-type reaction and the reactive oxygen species-mediated oxidation during glycoxidation.
Akagawa
Mitsugu
M
Department of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Sendai 981-8555, Japan.
Sasaki
Takeshi
T
Suyama
Kyozo
K
D001547:Benzaldehydes / Q000737:chemistry; D001596:Benzylamines / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D003641:Deamination; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D004492:Edetic Acid / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D005949:Glucose Oxidase / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D017665:Hydroxyl Radical; D007700:Kinetics; D008670:Metals / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D011765:Pyruvaldehyde / Q000737:chemistry; D017382:Reactive Oxygen Species / Q000737:chemistry
D001547:Benzaldehydes; D001596:Benzylamines; D002614:Chelating Agents; D016166:Free Radical Scavengers; D008670:Metals; D017382:Reactive Oxygen Species; D017665:Hydroxyl Radical; D011765:Pyruvaldehyde; D003300:Copper; D003847:Deoxyglucose; D004492:Edetic Acid; C030796:benzylamine; D005949:Glucose Oxidase; C016350:3-deoxyglucosone; D005947:Glucose; D009584:Nitrogen; D010100:Oxygen