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.
Kato-Toma
Y
Y
Suntory Institute for Bioorganic Research, Shimamoto, Osaka, Japan.
Ishiguro
M
M
D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D007700:Kinetics; D018716:Molecular Mimicry; D009842:Oligopeptides / Q000737:chemistry*; D010400:Penicillin G / Q000737:chemistry / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014443:Tyrosine / Q000737:chemistry*; D065093:beta-Lactamase Inhibitors
D004791:Enzyme Inhibitors; D009842:Oligopeptides; D065093:beta-Lactamase Inhibitors; C074312:lysyl-tyrosyl-lysine; D014443:Tyrosine; D010400:Penicillin G