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Chapter 23: Q10P (page 1076)

Acetolactatesynthasetransfers the acyl group of pyruvate to \(\alpha \)-ketobutyrate. This is the first step in the biosynthesis of the amino acid isoleucine. Propose a mechanism for this reaction.

Short Answer

Expert verified

In question it is mentioned that acetolactate synthase enzyme needs TTP for transferring acyl group from pyruvate to alpha-ketobutyrate to form alpha-aceto-alpha-hydroxybutyrate and remove carbon-dioxide.

Step by step solution

01

Acetolactate synthase role

In question it is mentioned that acetolactate synthase enzyme needs TTP for transferring acyl group from pyruvate to alpha-ketobutyrate to form alpha-aceto-alpha-hydroxybutyrate and remove carbon-dioxide.

02

Mechanism of action

The mechanism for the reaction is as follows:

  • First step is proton removal from TPP forming TPP-ylide.
  • TPP-ylide attaches to the carbonyl carbon of pyruvate.
  • The tetrahedral intermediate formed here easily undergoes decarboxylation by reaction giving TPP-enamine.
  • Addition of alpha-ketobutyrate occurs on the TPP-enamine carbon and afterward elimination from the tetrahedral intermediate occur forming alpha-aceto-alpha-hydroxybutyrate and regenerates the TPP-ylide.

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