Peroxidase-catalyzed-3-(glutathion-S-yl)-p,p'-biphenol formation.
Oxidation of p,p'-biphenol with horseradish peroxidase (HRP)-hydrogen peroxide in the presence of bovine serum albumin or with bone marrow cell homogenate-hydrogen peroxide resulted in the formation of reactive products that conjugate with protein. Glutathione prevented the protein binding. Glutathione readily reacted with p,p'-biphenoquinone, the principal oxidation product of p,p'-biphenol in the HRP-hydrogen peroxide system and resulted in the formation of several glutathione conjugates, p,p'-biphenol and small amounts of oxidized glutathione. The major glutathione conjugate was identified as 3-(glutathion-S-yl)-p,p'-biphenol by high field nuclear magnetic resonance and fast atom bombardment mass spectrometry. The same conjugate was formed in the bone marrow homogenate-hydrogen peroxide system. p,p'-Biphenoquinone reduction by glutathione to p,p'-biphenol without glutathione oxidation was explained by the rapid reduction of p,p'-biphenoquinone by 3-(glutathion-S-yl)-p,p'-biphenol.
D000818:Animals; D001713:Biphenyl Compounds / Q000378:metabolism*; D001853:Bone Marrow / Q000378:metabolism*; D002417:Cattle; D005978:Glutathione / Q000031:analogs & derivatives* / Q000378:metabolism*; D019803:Glutathione Disulfide; D006735:Horseradish Peroxidase / Q000378:metabolism*; D006861:Hydrogen Peroxide / Q000378:metabolism*; D006868:Hydrolysis; D007700:Kinetics; D010544:Peroxidases / Q000378:metabolism*; D012710:Serum Albumin, Bovine / Q000378:metabolism
D001713:Biphenyl Compounds; C050910:3-(glutathion-S-yl)-4,4'-biphenol; D012710:Serum Albumin, Bovine; D006861:Hydrogen Peroxide; D006735:Horseradish Peroxidase; D010544:Peroxidases; D005978:Glutathione; C027439:4,4'-dihydroxybiphenyl; D019803:Glutathione Disulfide