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Chapter 15: Q 89P (page 737)

The following compound has been found to be an inhibitor of penicillinase. The enzyme can be reactivated by hydroxylamine CH2OH. Propose a mechanism to account for the inhibition and for the reactivation.

Short Answer

Expert verified

The proposed mechanism is shown below.

Step by step solution

01

Step 1: Use of penicillinase enzyme

Penicillinase enzyme is used to resist penicillin.Four membered ring is opened using CH2OHgroup.

02

Step 2: Addition of groups

CH2OHgroup helps in the synthesis of bacterial cell walls. It attacks the carbonyl carbon of the four membered ring and forms a tetrahedral intermediate. This amide has more reactivity than the non-cyclic amides.

Addition of CH2OHgroup

03

Formation of phosphonyl enzyme

Penicillinase inhibitor has the ability to react with nucelophiles readily since it has a good leaving group. It is produced when CH2OHgroup attacks the penicillinase inhibitor, which is why hydroxyl group cannot react with penicillin.

Formation of phosphonyl enzyme

04

Reactivation of penicillinase

Hydroxylamine is used for the reactivation of penicillinase which releases phosphonyl enzyme. Here, the nucleophile is the oxygen.

Reactivation of penicillinase

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Most popular questions from this chapter

When treated with an equivalent of methanol, compound A, with the molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shown here. Identify compound A.

What are the products of the following reactions?

The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols.

a. Propose a mechanism for the Ritter reaction.

b. Why does the Ritter reaction not work with primary alcohols?

c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?

Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the direction of the transition state. The synthesis of antibody is carried out in the presence of a transition state analog-a stable molecule that structurally resembles the transition state. This causes an antibody to be generated that recognizes and binds to the transition state, thereby stabilizing it. For example, the following transition state analog has been used to generate a catalytic antibody that catalyzes the hydrolysis of structurally similar ester:

a. Draw a possible transition state for the hydrolysis of the reaction.

b. The following transition state analog is used to generate a catalytic antibody for the catalysis of ester hydrolysis. Draw the structure of an ester whose rate of hydrolysis would be increased by this catalytic antibody.

c. Design a transition state analog that catalyzes amide hydrolysis at the amide group indicated.

Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.
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