3. Some medications permanently inactivate their target enzyme by forming a covalent bond to an amino acid in the enzyme's active site. Aspirin is one example of a pharmaceutical that uses this type of mechanism. So is penicillin. As you saw in the last chapter, the active portion of penicillin is the B-lactam ring. Penicillin forms a covalent bond to serine in the active site of transpeptidase, an enzyme that is essential for forming the bacterial cell wall. Propose a mechanism for the inactivation of transpeptidase by penicillin and show the final product of the reaction. R. NH Он CH3 CH, -N- CH3 backbone

Introductory Chemistry: An Active Learning Approach
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Chapter22: Biochemistry
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3. Some medications permanently inactivate their target enzyme by forming a covalent bond to
an amino acid in the enzyme's active site. Aspirin is one example of a pharmaceutical that uses
this type of mechanism. So is penicillin. As you saw in the last chapter, the active portion of
penicillin is the B-lactam ring. Penicillin forms a covalent bond to serine in the active site
transpeptidase, an enzyme that is essential for forming the bacterial cell wall. Propose a
mechanism for the inactivation of transpeptidase by penicillin and show the final product of
the reaction.
NH
OH
CH3
CH2
CH3
backbone
penicillin
serine
Transcribed Image Text:3. Some medications permanently inactivate their target enzyme by forming a covalent bond to an amino acid in the enzyme's active site. Aspirin is one example of a pharmaceutical that uses this type of mechanism. So is penicillin. As you saw in the last chapter, the active portion of penicillin is the B-lactam ring. Penicillin forms a covalent bond to serine in the active site transpeptidase, an enzyme that is essential for forming the bacterial cell wall. Propose a mechanism for the inactivation of transpeptidase by penicillin and show the final product of the reaction. NH OH CH3 CH2 CH3 backbone penicillin serine
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