Amino group reactions of the sulfhydryl reagent methyl methanesulfonothioate. Inactivation of D-3-hydroxybutyrate dehydrogenase and reaction with amines in water

Abstract

Methyl methanesulfonothioate (MMTS) was used as a SH reagent. It inactivates D-3-hydroxybutyrate dehydrogenase in a manner that suggests that an amino group may have reacted with the reagent. NMR analysis of solutions of glycylglycine, glycine ethyl ester and imidazole with MMTS indicates that a reaction occurs which produces what is identified by its NMR signal as the methylsulfenamide of the amine. Caution should be used when MMTS is employed where reaction with an amine could give an undesired product.