The
adjacent image is a Spartan ELPOT surface of the Penicillin molecule. The
coloring indicates sites of electron density. Blue areas are characterized
by a low electron density and red areas mark high electron density. Thus,
the red areas are more negative in charge while the blue areas are less
negative. Penicillinase associates with Penicillin and adds a water molecule
to the bond between the nitrogen and the carbon of the carbonyl group in
the Beta-Lactam ring. The water molecule performs a nucleophilic attack
on the carbonyl carbon, creating a tetrahedral intermediate state in which
the oxygen of the water molecule is partially bound to the carbon and one
of the hydrogens from the water molecule is partially bound to the nitrogen
in the Beta-lactam ring. The bond between carbon and nitrogen breaks as
does the bond between oxygen and hydrogen. Simultaneously the bond between
carbon and and oxygen forms as does the bond between nitrogen and hydrogen.
The Beta-Lactam ring is destroyed, and the Penicillin molecule inactivated.