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
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
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F490d4977-d8d7-45bb-a464-fcd43c2931f1%2F08f842cd-5bf1-4625-996b-2351825d2c7d%2Fd8k3yxd_processed.jpeg&w=3840&q=75)
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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