Related Experiment Video
Updated: Jul 18, 2026

The Use of a β-lactamase-based Conductimetric Biosensor Assay to Detect Biomolecular Interactions
Published on: February 1, 2018
Exploring the chemistry of penicillin as a beta-lactamase-dependent prodrug
Carol C Ruddle1, Timothy P Smyth
1Department of Chemical and Environmental Sciences, University of Limerick, National Technological Park, County Limerick, Ireland.
Abstract:
The penam nucleus can be modified to behave as a beta-lactamase-dependent 'prodrug' by incorporation of a vinyl ester side chain at the 6-position. Enzyme-catalysed hydrolysis of the beta-lactam ring uncovers the thiazolidine-ring nitrogen as a nucleophile that drives a rapid intramolecular displacement on the side chain. Attachment of 7-hydroxy-4-methylcoumarin as the releasable group of this side chain generated a penicillin structure that can function as a fluorescence-based reporter substance/diagnostic for the presence of low levels of beta-lactamase enzyme in solution. Mechanistic details of the reaction pattern are documented and the scope and limitations of exploiting the structural modification are discussed.
Related Concept Videos
Production of Antibiotics
Inhibitors of Gram-positive Cell Wall Synthesis
Production of Pharmaceuticals
Combined Effects of Drugs: Synergism
Such synergistic combinations...
Prodrugs
Prodrugs help overcome...
Pharmacokinetic–Pharmacodynamic Relationship: Influence of Elimination Half-Life on Effect Duration

