title: 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) has been used as a sulfhydryl reagent. However, it inactivates D-3-hydroxybutyrate dehydrogenase in a manner that suggests that an amino group may have reacted with the reagent. Nuclear magnetic resonance (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. It is suggested that caution should be used when MMTS is employed where reaction with an amine could give an undesired product.
mesh_terms: D005998:Glycine; D006033:Glycylglycine; D006884:Hydroxybutyrate Dehydrogenase / Q000037:antagonists & inhibitors*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008741:Methyl Methanesulfonate / Q000031:analogs & derivatives* / Q000494:pharmacology; D011485:Protein Binding; D013439:Sulfhydryl Reagents / Q000494:pharmacology
chemical_list: D013439:Sulfhydryl Reagents; D006033:Glycylglycine; C014674:methyl methanethiosulfonate; D008741:Methyl Methanesulfonate; D006884:Hydroxybutyrate Dehydrogenase; D005998:Glycine