A "cephalosporin-like" cyclic depsipeptide: synthesis and reaction with beta-lactam-recognizing enzymes.
The cyclic depsipeptide 8-carboxy-3-phenylacetamido-3,4-dihydro-2H-1-benzopyran-2-one, a cyclic analog of aryl phenaceturates with structural similarity to cephalosporins, has been synthesized as a potential substrate/inhibitor of B-lactam-recognizing enzymes. It was found to be a tight-binding, poor substrate of class A beta-lactamases and an irreversible inhibitor of several DD-peptidases.
Adediran
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Department of Chemistry, Wesleyan University, Middletown, CT 06459, USA.
Cabaret
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Pratt
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Wakselman
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D002268:Carboxypeptidases / Q000037:antagonists & inhibitors; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D046929:Serine-Type D-Ala-D-Ala Carboxypeptidase; D013379:Substrate Specificity; D001618:beta-Lactamases / Q000378:metabolism*
D002511:Cephalosporins; D004791:Enzyme Inhibitors; D010456:Peptides, Cyclic; D002268:Carboxypeptidases; D046929:Serine-Type D-Ala-D-Ala Carboxypeptidase; D001618:beta-Lactamases