Regiospecific Syntheses of 6 alpha-(1R-Hydroxyoctyl)penicillanic Acid and 6 beta-(1R-Hydroxyoctyl)penicillanic Acid as Mechanistic Probes of Class D beta-Lactamases

摘要

The unique hydrophobic surface patches in class D beta-lactamases presented an opportunity for designing two compounds, 6 alpha-(1R-hydroxyoctyl)penicillanic acid and 6 beta-(1R-hydroxyoctyl)penicillanic acid, as mechanistic probes of these enzymes. In a sequence of three synthetic steps from benzhydryl 6,6-dibromopenicillanate, the targeted compounds were prepared in a stereospecific manner.