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Chapter 23: Q37E (page 783)

The amino acid leucine is biosynthesized from α-ketoisovalerate by the following sequence of steps. Show the mechanism of each.

Short Answer

Expert verified

The synthesis of leucine takes place from α-ketoisovalerate.

Step by step solution

01

Given sequence

The given reaction sequence is as follows,

02

Mechanism

Following are the steps involved in the process of synthesis of Leucine is,

  1. Aldol type reaction.
  2. Oxidation of alcohol with help of NAD+
  3. Decarboxylation
  4. Condensation with NH3 followed by reducing the desired product.

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Most popular questions from this chapter

Which of the following compounds can probably be prepared by a mixed aldol reaction? Show the reactants you would use in each case.

When 2-methyl cyclohexanone is converted into an enamine, only one product is formed despite the fact that the starting ketone is unsymmetrical. Build molecular models of the two possible products and explain the fact that the sole product is the one with the double bond opposite the methyl-substituted carbon.

The Darzens reaction involves a two-step, base-catalyzed condensation of ethyl chloroacetate with a ketone to yield an epoxy ester. The first step is a carbonyl condensation reaction, and the second step is an SN2 reaction. Write both steps, and show their mechanisms.

The major product formed by intramolecular aldol cyclization of 2,5-heptanedione (Problem 23-51) has two singlet absorptions in the 1H NMR spectrum, at 1.65 d and 1.90 d, and has no absorptions in the range 3 to 10 d. What is its structure?

How would you prepare the following compounds from cyclohexanone?
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