A series of inhibitors of angiotensin converting enzyme (ACE, dipeptidyl carboxypeptidase, EC 3.4. 15.1) is described which addresses certain conformational aspects of the enzyme- inhibitor interaction. In this study the alanylproline portion of the potent ACE inhibitor enalaprilat (2) is replaced by a aeries of monocyclic ladams containing the required recognition and binding elements. In order to more fully assess the lactam ring ...