Dehydrooligopeptides. XIII. Selective Enzymatic Hydrolysis of N-Protected α-Dehydroglutamic Acid Diesters and Their Analogs Using Papain as Catalyst

Article abstract of DOI:10.1246/bcsj.64.3575

Since the α-ester of α,γ-dimethyl N-benzyloxycarbonyl-α-dehydroglutamate (ΔGlu) was found to be hydrolyzed using papain, a variety on N-protected α-dehydroglutamates and their analogs, both esters of which were the same or different from each other, were newly synthesized and subjected to a similar hydrolysis.Although the substrates, with bulkier ester group at the γ- as well as α-positions, were found to become difficult to hydrolyze, the kind and size of the N-protecting group did not effect the hydrolysis.Moreover, it was found that the length of side chain of the substrate greatly influenced hydrolysis.The present study suggest that papain may become a useful tool for the hydrolysis and coupling of ΔGlu with α-amino acid or peptide.