6-(Methoxymethylene)penicillanic acid: inactivator of RTEM beta-lactamase from Escherichia coli.
The Z and E isomers of 6-(methoxymethylene)-penicillanic acid have been synthesized, and their interaction with the RTEM beta-lactamase has been studied. The Z isomer is an inhibitor and an inactivator of the enzyme, and there is some similarity between its behavior and that of other mechanism-based inactivators such as clavulanic acid and the penam sulfones. Kinetic analysis of the interaction of the enzyme with the Z isomer has allowed a detailed evaluation of the factors that are important in the design of anti-beta-lactamase agents. In contrast to the Z compound, the E isomer of 6-(methoxymethylene)penicillanic acid is not a substrate, an inhibitor, or an inactivator of the enzyme.
D001667:Binding, Competitive; D055598:Chemical Phenomena; D002621:Chemistry; D019818:Clavulanic Acid; D002969:Clavulanic Acids / Q000494:pharmacology; D004926:Escherichia coli / Q000201:enzymology*; D006868:Hydrolysis; D007536:Isomerism; D007700:Kinetics; D010397:Penicillanic Acid / Q000494:pharmacology* / Q000031:analogs & derivatives; D010400:Penicillin G / Q000378:metabolism; D013056:Spectrophotometry, Ultraviolet; D013407:Sulbactam; D065093:beta-Lactamase Inhibitors; D001618:beta-Lactamases
D002969:Clavulanic Acids; D065093:beta-Lactamase Inhibitors; D019818:Clavulanic Acid; D010397:Penicillanic Acid; C044546:6-(methyoxymethylene)penicillanic acid; D001618:beta-Lactamases; C034413:beta-lactamase TEM-1; D010400:Penicillin G; D013407:Sulbactam