Page 158 - Medicinal Chemistry Self Assessment
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2.10 Cefprozil 147
6. Like the penicillins, the cephalosporins suffer from chemical instability of the β-lactam bond. Chem-
ical hydrolysis of this bond renders the drugs in the class of anti-infective agents inactive. This bond
is also subject to cleavage by β-lactamases (due to the presence of a nucleophilic serine side chain
[CH OH] within the active site of the enzyme). Show how the β-lactam bond can be hydrolyzed by
2
chemical and enzymatic (β-lactamase) mechanisms.
Answer
Chemical Hydrolysis
OH -
Enzymatic Hydrolysis
Go to Section 1.10 [Link to section 1.10 title]
