Dehydrooligopeptides. XV. Useful Syntheses of Dehydrodipeptides by the Enzymatic Coupling of α-Dehydroglutamate with Various α-Amino Acid Amides Using Proteases

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Abstract
Novel enzymatic syntheses of various dehydrodipeptides by the coupling of α,γ-dimethyl N-benzyloxycarbonyl(Z)-α-dehydroglutamate [Cbz–ΔGlu(OMe)–OMe; 1] with α-amino acid amides (H–AA–NHR) using proteases, such as papain and α-chymotrypsin A (CT), are described. It was found that there was conspicuous difference between the catalytic actions of papain and CT toward 1. In the case of papain, the selective coupling of α-ester of 1 with H–AA–NHR took place to give Cbz–ΔGlu(OMe)–AA–NHR, while in the case of CT the coupling of γ-ester of 1 proceeded predominantly to give Cbz–ΔGlu(AA–NHR)–OMe. The present study suggests that both papain and CT may become a versatile tool for the organic synthesis by the coupling of not only ΔGlu derivatives but also the other α-dehydroamino acids with α-amino acids or peptides.