Q69E - Organic Chemistry (Mcmurry)

Question

In nature, the enzyme chorismate mutase catalyses a Claisen rearrangement of chorismate that involves both the terminal double bond and the double bond with the highlighted carbon. What is the structure of prephenate, the biological precursor to the amino acids phenylalanine and tyrosine?

                        Chorismate

Step-by-Step Solution

Answer

The answer is 

                                                   Prephenate

Step 1: Claisen rearrangement

The Claisen rearrangement is the rearrangement of allyl vinyl ether compounds to form new carbon-carbon bonds. The beta-gamma carbonyl compounds are formed as the product of this rearrangement reaction.

Step 2: Explanation

The Chorismate compound undergo Claisen rearrangement to give the product Prephenate as shown below.

               Chorismate                                                        Prephenate

The carbon-oxygen bond is cleaved to give a new carbon-carbon bond. The stereochemistry of the compound is retained in the product.