Journal
ACS CHEMICAL BIOLOGY
Volume 8, Issue 10, Pages 2112-2116Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cb400200h
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Funding
- Medical Research Council (MRC) [G1100135]
- Cancer Research UK (CRUK)
- British Heart Foundation (BHF)
- Biotechnology and Biological Sciences Research Council (BBSRC)
- Medical Research Council [G1100525, G1100135] Funding Source: researchfish
- MRC [G1100135, MR/K018779/1] Funding Source: UKRI
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beta-Lactam antibiotics react with penicillin binding proteins (PBPs) to form relatively stable acyl-enzyme complexes. We describe structures derived from the reaction of piperacillin with PBP3 (Pseudomonas aeruginosa) including not only the anticipated acyl-enzyme complex but also an unprecedented complex with (5S)-penicilloic acid, which was formed by C-5 epimerization of the nascent (5R)-penicilloic acid product. Formation of the complex was confirmed by solution studies, including NMR. Together, these results will be useful in the design of new PBP inhibitors and raise the possibility that noncovalent PBP inhibition by penicilloic acids may be of clinical relevance.
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