Abstract
alpha-Benzyl-2-oxo-1,3-oxazolidine-4-acetic acid (BOOA) having (alpha R,4S) and (alpha S,4R) configurations were designed and synthesized as a novel type of mechanism-based inactivators for carboxypeptidase A (CPA), and kinetic analysis demonstrated that they indeed inhibit the enzyme in a time-dependent manner with the second order inhibitory rate constants (kinact/KI) of 1.52 and 1.39 M-1 s-1 for (alpha S,R4)-BOOA and (alpha R,4S)-BOOA, respectively.
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