ORGANIC CHEMISTRY W/OWL
ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
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Chapter 29.SE, Problem 24MP

One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of xylulose 5-phosphate with ribose 5-phosphate in the presence of a transketolase to give glyceraldehyde 3-phosphate and sedoheptulose 7-phosphate.

Chapter 29.SE, Problem 24MP, One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of xylulose

(a) The first part of the reaction is nucleophilic addition of thiamin diphosphate (TPP) ylide to xylulose 5-phosphate, followed by a retro-aldol cleavage to give glyceraldehyde 3-phosphate and a TPPcontaining enamine. Show the structure of the enamine and the mechanism by which it is formed.

(b) The second part of the reaction is addition of the enamine to ribose 5-phosphate followed by loss of TPP ylide to give sedoheptulose 7-phosphate. Show the mechanism.

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