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#antibiotic mechanism

2 public questions tagged with this topic.

Which enzyme is inhibited by penicillin?

Bacterial peptidoglycan final crosslinking step catalyzed by transpeptidases penicillin binding proteins class B enzymes PBP2 for elongation, PBP3 FtsI for division. They cleave C terminal D alanine D alanine dipeptide from pentapeptide side chain MurNAc L Ala D Glu mDAP D Ala D Ala, forming acyl enzyme intermediate through active site serine nucleophile, then transfer to amino group acceptor meso diamino pimelic acid or L lysine of neighboring strand creating peptide crossbridge essential for wall rigidity. Beta lactam antibiotics penicillin contain four membered ring mimicking D Ala D Ala conformation fitting active site, acylating catalytic serine irreversibly forming stable penicilloyl enzyme unable to deacylate, blocking transpeptidation. Nascent peptidoglycan remains linear uncrosslinked degraded by endogenous autolysins lytic transglycosylases leading to osmotic lysis especially during growth when wall remodeling high. Gyrase target quinolones, RNA polymerase target rifampicin, ribosomal peptidyl transferase chloramphenicol. Thus penicillin specifically inhibits transpeptidase activity, mechanistic basis for bactericidal action and synergy with beta lactamase inhibitors clavulanate restoring efficacy against resistant strains.

Ref: Tipper & Strominger, PNAS 1965, Penicillin inhibits transpeptidase PBP crosslinking peptidoglycan.

The mechanism of action of macrolides (e.g., erythromycin) is:

Macrolides such as erythromycin, azithromycin and clarithromycin belong to group characterized by large 14-, 15- or 16-membered lactone rings decorated with deoxy sugar moieties L-cladinose and desosamine that confer binding specificity. They lodge within the nascent peptide exit tunnel of the large ribosomal subunit. Bacterial ribosomes comprise small 30S and large 50S subunits; 50S contains 23S rRNA that forms the peptidyl transferase center and tunnel spanning subunit. Macrolides bind at nucleotides 2058 and 2059 of domain V of 23S rRNA near the peptidyl transferase center, partially occluding the tunnel with sugar moieties projecting inward. Peptide chain elongation proceeds for a few amino acids until steric hindrance prevents translocation of peptidyl-tRNA from A to P site, causing premature dissociation of incomplete peptidyl-tRNA and halting protein synthesis. This halts translation in a selective manner leaving DNA synthesis and folate metabolism untouched and producing bacteriostatic effect at low concentrations. Methylation of adenine at A2058 by erm methylases encoded by ermB confers high-level resistance of MLS-B phenotype, highlighting precise molecular contact point and explaining cross-resistance to lincosamides and streptogramin B.

Ref: Alberts et al., Molecular Biology of the Cell, 7th ed., Chapter 7: Macrolides Binding to 50S Ribosomal Subunit.