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.

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@article{Brenner19846MethoxymethylenepenicillanicAI, title={6-(Methoxymethylene)penicillanic acid: inactivator of RTEM beta-lactamase from Escherichia coli.}, author={Dr. Gerhard Brenner and Jeremy Knowles}, journal={Biochemistry}, year={1984}, volume={23 24}, pages={5839-46} }