Some studies on peptide analogues involving the sulphinamide group

Abstract

The title compounds are of interest as possible transition state inhibitors of peptidases. A route to N(alkylsulphinyl)amino acids is described. A method for generating α-benzamidosulphinamides is reported; a general route to such systems failed owing to the difficulty of removing the protecting group and the apparent instability of α-amino sulphinamides. A crystal structure on the N-phthalimido-protected α-sulphinamide 16a showed the tetrahedral disposition of substituents around the sulphur atom and the deviation from planarity about the sulphinamide nitrogen atom.