Effects of intramolecular proton acceptors located near sulfhydryl groups on sulfhydryl compounds for acrylamide elimination

To explore the effects of intramolecular neighboring groups on sulfhydryl group reactivity in acrylamide removal, the reactions of three sulfhydryl-containing flavoring substances with derived structures, 1-propanethiol, 3-mercaptopropionic acid, and cysteine, with acrylamide were investigated. The results showed that the activation energies of the reactions decreased with the introduction of amino and carboxyl groups. Additional comparison reactions showed that other proton acceptors also promote the reactions of sulfhydryl groups with acrylamide. However, the reactivity was not enhanced if the proton acceptor was located far from the sulfhydryl group. This suggested that sulfhydryl compounds with the molecular structure of proton acceptors on the carbons located β or/and γ to the sulfhydryl group were efficient in eliminating acrylamide, and the results are expected to serve as a guide in the search for effective acrylamide elimination agents.