Enzymatic S-de-ethylation and the mechanism of S-dealkylation.
An NADPH- and oxygen-dependent enzymatic system responsible for the formation of acetaldehyde from ethylthioethers is present in the 9000 g supernatant fraction of rat liver. This system appears to be quite similar to the one responsible for the formation of formaldehyde from methylthioethers. Although both of these systems appears to be microsomal mixedoxidase systems, several anomalous findings regarding the mechanism of microsomal S-dealkylation have been observed and have led us to the conclusion that the mechanism of this reaction is more complex than originally believed. A scheme is postulated by which an enzyme in the soluble fraction causes microsomal sulfoxidation of alkylthioethers to alkylsulfoxides, followed by metabolism of the alkylsulfoxides to aldehydes.
D000079:Acetaldehyde / Q000032:analysis; D000818:Animals; D002458:Cell Fractionation; D002642:Chick Embryo; D003640:Dealkylation; D004980:Ethane / Q000031:analogs & derivatives / Q000378:metabolism; D005557:Formaldehyde / Q000032:analysis; D008297:Male; D015122:Mercaptopurine / Q000031:analogs & derivatives / Q000378:metabolism; D008697:Methane / Q000031:analogs & derivatives / Q000378:metabolism; D008861:Microsomes / Q000378:metabolism; D008862:Microsomes, Liver / Q000201:enzymology*; D008956:Models, Chemical; D009249:NADP / Q000378:metabolism; D010088:Oxidoreductases / Q000378:metabolism*; D011687:Purines / Q000378:metabolism; D051381:Rats; D013438:Sulfhydryl Compounds / Q000378:metabolism; D013440:Sulfides / Q000378:metabolism*; D013441:Sulfinic Acids / Q000378:metabolism
D011687:Purines; D013438:Sulfhydryl Compounds; D013440:Sulfides; D013441:Sulfinic Acids; D005557:Formaldehyde; D009249:NADP; D015122:Mercaptopurine; D010088:Oxidoreductases; D000079:Acetaldehyde; D004980:Ethane; D008697:Methane