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Acetoacetate decarboxylase catalyzes the decarboxylation of acetoacetate via the formation of a Schiff base between the ketone of acetoacetate and its Lys 115. Which of the following is most likely correct?

a) Lys 115 acts as a general acid
b) Lys 115 acts as a general base
c) Schiff base formation stabilizes the transition state
d) Schiff base formation inhibits catalysis

1 Answer

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Final answer:

The correct statement about the role of Lys 115 in the decarboxylation of acetoacetate is that Schiff base formation stabilizes the transition state. Lys 115 forms a covalent Schiff base with the ketone of acetoacetate, aiding in stabilizing the transition state for decarboxylation. Therefore, correct option is c.

Step-by-step explanation:

The student asked which statement is most likely correct concerning the role of Lys 115 in the decarboxylation of acetoacetate via the formation of a Schiff base.

Among the options given, the statement that Schiff base formation stabilizes the transition state (c) is correct. During the catalysis by acetoacetate decarboxylase, the Lys 115 residue acts as a nucleophile, forming a covalent bond with the ketone of acetoacetate to create a Schiff base.

This bonding facilitates the decarboxylation by stabilizing the transition state and enabling the keto group to be more readily decarboxylated.

The statement that Lys 115 acts as a general base (b) is not accurate in the context of Schiff base formation during this reaction, as it does not abstract a proton but rather forms a covalent bond.

The correct role is that of a nucleophilic catalyst which is different from acting as a general base or acid. Therefore, option c) Schiff base formation stabilizes the transition state, is most likely correct.

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