The formation and metabolism of N-hydroxymethyl compounds. Part 6. The synthesis of S-amidomethyl-, S-ureidomethyl-, and S-(1,3,5-triazin-2-ylaminomethyl)-glutathione derivatives

Abstract

Treatment of N-hydroxymethyl and N-alkoxymethyl compounds with glutathione or N-acetylcysteine in trifluoroacetic acid affords the corresponding glutathione or N-acetylcysteine derivatives in high yield. Alkoxymethylureas are formed by the condensation of ureas with formaldehyde and alcohols under basic conditions; the implications of this observation are discussed with reference to possible biochemical mechanisms.