Azapeptides: a new class of angiotensin-converting enzyme inhibitors.
A class of potent inhibitors of angiotensin-converting enzyme (dipeptidyl carboxypeptidase, E.C. 3.4.15.1) is reported, in which an alpha-aza substitution into the substituted N-carboxymethyl dipeptide structure of enalapril is made. The inhibitors 2 exhibit striking alterations in their conformational and acid-base properties due to the aza substitution, as is clear from pKa data and the x-ray crystal structure of a model azapeptide. In spite of this, they bind tightly to the enzyme, with inhibitor potency comparable to that of captopril.
D000806:Angiotensin-Converting Enzyme Inhibitors; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D010455:Peptides / Q000138:chemical synthesis* / Q000494:pharmacology; D011487:Protein Conformation; D013329:Structure-Activity Relationship
D000806:Angiotensin-Converting Enzyme Inhibitors; D001372:Aza Compounds; D007202:Indicators and Reagents; D010455:Peptides