Reaction of Lys-Tyr-Lys triad mimics with benzylpenicillin: insight into the role of Tyr150 in class C beta-lactamase.

Small and simple molecules mimicking a Lys-Tyr-Lys triad and some 'mutant' derivatives were designed and synthesized. These-compounds react with benzylpenicillin in water (75mM phosphate buffer, pH 7), apparently through general base assistance by the phenolic moiety. Class C beta-lactamase has a Lys-Tyr-Lys triad in its active site, and our finding gives some insight into the role of this triad in the enzymatic beta-lactam hydrolysis mechanism.