The Journal of organic chemistry

Controlled synthesis of peptides in aqueous medium. III. Use of Leuch's anhydrides in the synthesis of di-peptides. Mechanism and control of side reactions

RF Hirschmann

Index: Hirschmann,R. et al. Journal of Organic Chemistry, 1967 , vol. 32, p. 3415 - 3425

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Citation Number: 103

Abstract

The successful use of N-carboxy-a-amino acid anhydrides (NCA's) in the controlled synthesis of optically pure dipeptides in aqueous medium is described. High yields of dipeptides were obtained by adding the crystalline NCA directly to an aqueous solution of an amino acid at 0-2'and generally at pH 10.2 with rapid mixing of reactants, thus minimizing side reactions. In the case of relatively insoluble NCA's, rapid mixing enhances the rate of ...