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Solved: Catalytic antibodies catalyze a reaction by
Chapter 16, Problem 94P(choose chapter or problem)
Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the direction of the transition state. The synthesis of the 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 will recognize and bind 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 the structurally similar ester:
a. Draw the transition state for the hydrolysis 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 would catalyze amide hydrolysis at the amide group indicated.
Questions & Answers
QUESTION:
Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the direction of the transition state. The synthesis of the 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 will recognize and bind 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 the structurally similar ester:
a. Draw the transition state for the hydrolysis 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 would catalyze amide hydrolysis at the amide group indicated.
ANSWER:
Solution 94P
In this multi-part exercise, we’re told that catalytic antibodies can catalyze a reaction by aligning the conformation of the substrate to match that of the transition state. The antibody synthesis is performed in the presence of a molecule that mimics that shape of the transition state, also known as an analog. This generates antibodies that recognize and bind to the transition state, which stabilizes it.
As an example, consider the following compound. This material is a transition state analog and it’s used to generate a catalytic antibody that can catalyze ester hydrolysis for structurally similar esters.
The following hydrolysis reaction is one which can be catalyzed by the above transition state analog.
Note the structural similarities in this reaction’s starting material and the transition state analog used as the catalyst. The exercise now asks us a series of questions about this topic.