N-Trifluoroacetyl-dipeptide methyl ester類の合成(その1)

Abstract

A number of N-trifluoroacetyl-dipeptide methyl esters in which N-terminal aminoacyl substituents are Gly, L-Ala, L-Val, L-Leu, L-Ileu, L-Pro, L-Orn and L-Phe were prepared for the study of the gas-chromatographic separation. Carbobenzoxy-dipeptide methyl esters were prepared from carbobenzoxy-amino acids and amino acid methyl esters by the mixed anhydride procedure. These dipeptide derivatives were decarbobenzoxylated with hydrogen bromide in acetic acid or by catalytic hydrogenation. The products were then trifluoroacetylated with methyl trifluoroacetate in the presence of triethyl amine to yield N-trifluoroacetyl-dipeptide methyl esters. The dipeptides containing L-Orn were able to be separated gas-chromatographically also in the form of ditrifluoroacetyl derivatives. The glycyl-amino acid derivatives were prepared also from N-trifluoroacetyl-glycine anhydride and amino acid methyl esters by the procedure of F. Weygand.