Reaction of Glycylglycine with Formaldehyde in the Presence of Cupric Ion

Abstract

Abstract The reaction mixture of glycylglycine with formaldehyde in an alkaline aqueous solution containing cupric ion at 100°C gave seven ninhydrin positive components which were identified as follows; α-hydroxymethylserine, serine, glycine, 3-carboxymethyl-4-imidazolidone, α-hydroxymethylseryl-glycine, serylglycine and glycylglycine. The yield of serylglycine increased in proportion to the amount of cupric ion, whereas the yield of 3-carboxymethyl-4-imidazolidone was maximum when no cupric ion was added. A single-step synthesis in preparative scale of serylglycine or 3-carboxymethyl-4-imidazolidone under the best condition was achieved in a good yield.