EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
9th Edition
ISBN: 9781305084391
Author: McMurry
Publisher: CENGAGE L
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Chapter 29.SE, Problem 23MP

One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of sedoheptulose 7-phosphate with glyceraldehydes 3-phosphate in the presence of a transaldolase to yield erythrose 4-phosphate and fructose 6-phosphate.

Chapter 29.SE, Problem 23MP, One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of

(a) The first part of the reaction is the formation of a protonated Schiff base of sedoheptulose 7-phosphate with a lysine residue in the enzyme followed by a retro-aldol cleavage to give an enamine plus erythrose 4-phosphate. Show the structure of the enamine and the mechanism by which it is formed.

(b) The second part of the reaction is a nucleophilic addition of the enamine to glyceraldehyde 3-phosphate followed by hydrolysis of the Schiff base to give fructose 6-phosphate. Show the mechanism.

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