A “cephalosporin-like” cyclic depsipeptide: Synthesis and reaction with ß-lactam-recognizing enzymes

The cyclic depsipeptide 8-carboxy-3-phenylacetamido-3,4-dihydro-3H-1-benzopyran-2-one, a cyclic analog of aryl phenaceturates with structural similarity to cephalosporins, has been synthesized as a potential substrate/inhibitor of ß-lactam-recognizing enzymes. It was found to be a tight-binding, poor substrate of class A ß-lactamases and an irreversible inhibitor of several DD-peptidases.