Abstract
A designed library of tripeptidomimics of Ornithyl-Proline (Orn-Pro) and Lysyl-Proline (Lys-Pro) conjugated with various unnatural amino acids and carboxylic acid derived heterocyclics was synthesized and screened for possible inhibitors of angiotensin-converting enzyme (ACE). Among the tripeptidomimics 10[MTP-Orn-Pro], 11[HTP-Orn-Pro], 14[TA-Orn-Pro] and 20[BPA-Orn-Pro] showed prominent inhibition with IC 50 values in micromolar concentrations. Structure–activity relationship study indicated that C 3 side chain of Orn as compared to C 4 side chain of Lys at P 1 ′ position was better suited to inhibit ACE, with propionic acid (C 3) derived heterocyclics and unnatural amino acids.
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