If the biosynthesis of palmitic acid were carried out with CD3COSR and nondeuterated malonyl thioester, how many deuterium atoms would be incorporated into palmitic acid?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter29: The Organic Chemistry Of Metabolic Pathways
Section29.SE: Something Extra
Problem 55AP: In step 7 of fatty-acid biosynthesis (Figure 29-5), dehydration of a -hydroxy thioester occurs to...
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If the biosynthesis of palmitic acid were carried out with CD3COSR and nondeuterated malonyl thioester, how many deuterium atoms would be incorporated into palmitic acid?

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Step 1

For the synthesis of palmitic acid, in the first step CD3COSR and nondeuterated malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester. The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

 

 

 

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