Competing reactions of disulphides
and hydroxyl anion – QM study
Martin Krupièka, Dominik Marx
Lehrstuhl für Theoretische
Bochum, 44780 Bochum, Germany
Disulphide moiety is found in the majority of proteins and attack by the hydroxyl anion can be expected in the water environment. The studied competing reaction mechanisms encompass (i) nucleophilic substitution on sulphur with two different angles of attack, (ii) nucleophilic substitution on a-carbon, (iii) eliminatinon from β - or (iv) α -carbon and (v) internal elimination reaction without participation of OH- nucleophile. The minimal energy pathways do not allow for unequivocal distiction of the preffered mechanism.