Studies on 2-Aziridinecarboxylic Acid, II. A Novel Synthesis of Threonine <i>O</i>-Peptide Derivatives <i>via</i> (2<i>S</i>,3<i>S</i>)-3-Methyl-2-aziridinecarboxylic Acid

Abstract

Abstract A new synthesis of threonine O-peptides via the ring opening reaction of aziridine peptide with carboxylic acid has been investigated. Benzyl (2S,3S)-1-[N-(benzyloxycarbonyl)glycyl]-3-methyl-2-aziridinecarbonylglycinate was treated with several N-protected amino acids or dipeptides at their mixed melting point, and the corresponding O-aminoacyl or dipeptidyl esters of l-threonine peptide derivative were obtained in good yields without racemization.