title: Molecular orbital study on the glutathione-dependent detoxication of ozonides.
abstract: The present paper describes a theoretical study on the mechanism underlying the reaction of cellular glutathione (GSH) with polyunsaturated fatty acid ozonides. The reaction can be catalyzed by glutathione S-transferases and leads to detoxication of the ozonides. Semi-empirical molecular orbital computer calculations suggest that the reaction of glutathione with ozonides involves a nucleophilic attack at one of the carbon atoms of the ozonide ring, instead of at one of the peroxidic oxygen atoms of the ozonide ring. This implies a mechanism different from that of the glutathione S-transferase-mediated reaction with hydroperoxides, previously proposed for the glutathione-dependent detoxication of fatty acid ozonides.
authors: Department of Toxicology, Agricultural University, Wageningen, Netherlands.
authors: R A
authors: RA
authors: Hempenius
authors: J
authors: J
authors: de Vries
authors: I M
authors: IM
authors: Rietjens
mesh_terms: D003201:Computers; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000378:metabolism; D005978:Glutathione / Q000737:chemistry* / Q000378:metabolism; D005982:Glutathione Transferase / Q000378:metabolism*; D008658:Inactivation, Metabolic; D010126:Ozone / Q000737:chemistry* / Q000378:metabolism
chemical_list: D005231:Fatty Acids, Unsaturated; D010126:Ozone; D005982:Glutathione Transferase; D005978:Glutathione