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?

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter20: Carbohydrates
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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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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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