Structure-based optimization of cephalothin-analogue boronic acids as β-lactamase inhibitors

S Morandi, F Morandi, E Caselli, BK Shoichet…

Index: Morandi, Stefania; Morandi, Federica; Caselli, Emilia; Shoichet, Brian K.; Prati, Fabio Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 3 p. 1195 - 1205

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Citation Number: 51

Abstract

Boronic acids have proved to be promising selective inhibitors of β-lactamases, acting as transition state analogues. Starting from a previously described nanomolar inhibitor of AmpC β-lactamase, three new inhibitors were designed to gain interactions with highly conserved residues, such as Asn343, and to bind more tightly to the enzyme. Among these, one was obtained by stereoselective synthesis and succeeded in placing its anionic group into the ...