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. Author manuscript; available in PMC: 2014 Jan 15.
Published in final edited form as: Anal Chem. 2012 Dec 28;85(2):1065–1072. doi: 10.1021/ac3028273

Scheme 1.

Scheme 1

Formation of SA-Cys34 sulfenamide, sulfinamide, and sulfonamide adducts with N-oxidized metabolites of PhIP. The genotoxic metabolite HONH-PhIP undergoes oxidation to form Nitroso-PhIP, which forms a sulfinamide adduct, following rearrangement of the semimercaptal. HONH-PhIP forms reactive sulfate or acetate esters following conjugation reactions with phase II enzymes. These esters of HONH-PhIP react with SA to form the sulfenamide adduct at Cys34. The superoxide generated during the oxidation of HONH-PhIP to Nitroso-PhIP, or other reactive oxygen species (ROS), can convert the labile sulfenamide and sulfinamide adducts of SA-Cys34-PhIP to the stable sulfonamide linkage.