Inhibitors of porcine pancreatic elastase. Peptides incorporating α-aza-amino acid residues in the P1 position

Abstract

Inhibitors of porcine pancreatic elastase based on one of the repeating peptide sequences (Gly-Val-Gly-Val-Ala) present in elastin have been prepared. Most of these contain an α-aza-amino acid benzyl ester group at the C-terminus and an N-[(1-methoxycarbonylalkyl)carbamoyl]- or an N-[(1-carboxyalkyl)-carbamoyl]-group at the N-terminus. The most potent analogue of the series, N-[(1-carboxyethyl)-carbamoyl]-valylglycyl-α-aza-alanine benzyl ester (53) was ca. 60-fold more potent than one of the azapeptide inhibitors of elastase (Ac-Ala-Ala-Azala-ONp) reported earlier.