Influence of the structure of amine components on carboxypeptidase Y catalyzed amide bond formation

Carboxypeptidase Y catalyzed reactions between a common acyl component (Bz-Ala-OMe) and a variety of amine compounds are described. The α-amino acid amides tested were—with the exception of isoglutamine— incorporated in high yields (70–95%). For the free α-amino acids, the yields were below 60% and fluctuated widely. For the cases examined, the enzyme only reacted with thel-enatiomers of these compounds. Dipeptides were not accepted as amine components. Glycinonitril, glycine-n-methyl amide and threonine-n-methyl amide reacted in low yields (