Benzo[a]pyrene Is a Carcinogenic Polyaromatic Hydrocarbon Found in Cigarette Smoke

Essay

Benzo[a]pyrene is a carcinogenic polyaromatic hydrocarbon found in cigarette smoke that is converted by enzymes in the body to a diol epoxide.
This diol epoxide product can react with nucleophiles on DNA and thus promote cancer. (This is one of the main reasons that cigarette smoke is carcinogenic.) The body can neutralize this toxin by reacting it with glutathione, a thiol. Representing glutathione as R-SH, show two products that might form when glutathione reacts with the diol epoxide, including their stereochemistry. Although acids and bases for this reaction are typically provided by the enzymes that catalyze this transformation, assume that -OH is the base and H₂O is the acid where acids and bases are necessary.