Question 4 A series of 6-arylmethylidene penicillin-based sulfone inhibitors (1) were developed as a combination treatment to restore the efficacy of a series of B-lactam antibiotics in bacterial species that carry carbapenem- hydrolyzing B-lactamases. The proposed mechanism of inhibition involves the formation of the enzyme-molecule adduct 2. Please provide an arrow-pushing mechanism using strictly serine as a nucleophile. [Note: Remember that water is present as well] beta-lactamase SO. Me `Me OR "Me Me OR Co,H H. co,H Ser penicillin 1 2

Biochemistry
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Chapter1: Biochemistry: An Evolving Science
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Just in case, the question is at the very end and please be sure to use serine only.
Question 4
A series of 6-arylmethylidene penicillin-based sulfone inhibitors (1) were developed as a
combination treatment to restore the efficacy of a series of B-lactam antibiotics in bacterial species that carry carbapenem-
hydrolyzing B-lactamases. The proposed mechanism of inhibition involves the formation of the enzyme-molecule adduct 2.
Please provide an arrow-pushing mechanism using strictly serine as a nucleophile. [Note: Remember that water is present
as well]
R.
beta-lactamase
ȘO2
Me
Me
OR
'Me
Me OR
"co,H
Ser
penicillin
1
2
Transcribed Image Text:Question 4 A series of 6-arylmethylidene penicillin-based sulfone inhibitors (1) were developed as a combination treatment to restore the efficacy of a series of B-lactam antibiotics in bacterial species that carry carbapenem- hydrolyzing B-lactamases. The proposed mechanism of inhibition involves the formation of the enzyme-molecule adduct 2. Please provide an arrow-pushing mechanism using strictly serine as a nucleophile. [Note: Remember that water is present as well] R. beta-lactamase ȘO2 Me Me OR 'Me Me OR "co,H Ser penicillin 1 2
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