Chemistry of penicillins ( key features of the structure)

 Penicillins are a group of β-lactam antibiotics originally obtained from Penicillium

moulds, principally P. chrysogenum and P. rubens.
 It is made up of an enclosed dipeptide formed by the condensation of L-cysteine and
D-valine. This results in the formations of β-lactam and thiazolidinic rings.
 The chemistry of penicillins is characterized by their structure, functional groups, and
mechanisms of action.
 β-Lactam Ring: Penicillins belong to a class of antibiotics known as β-lactam
antibiotics due to the presence of a β-lactam ring in their chemical structure. The β-
lactam ring is a four-membered cyclic structure consisting of three carbon atoms and
one nitrogen atom.
 Thiazolidine Ring: Penicillins also possess a thiazolidine ring fused to the β-lactam
ring. The thiazolidine ring contributes to the stability and overall structure of
penicillins.
 Amide Group: Penicillins contain an amide group (-CONH-) attached to the β-
lactam ring. This amide group plays a crucial role in the mechanism of action of
penicillins by interacting with bacterial enzymes known as penicillin-binding proteins
(PBPs).
 Side Chain: Penicillins have a variable side chain attached to the β-lactam ring,
which can differ among different penicillin derivatives. The nature and structure of
the side chain determine the spectrum of activity, stability, and pharmacokinetic
properties of each penicillin.
 Mechanism of Action: Penicillins exert their antibacterial activity by inhibiting the
synthesis of bacterial cell walls. The β-lactam ring of penicillins mimics the structure
of the D-alanine-D-alanine portion of the bacterial cell wall precursors. Penicillins
bind irreversibly to PBPs, which are enzymes involved in cross-linking the
peptidoglycan chains of the cell wall. This binding inhibits the transpeptidase activity
of PBPs, resulting in weakened cell walls and eventual cell lysis.