Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 29.SE, Problem 22MP
Interpretation Introduction

Interpretation:

The pentose phosphate pathway for degrading sugars (see Problem 29-21) is the conversion of ribose 5-phosphate to glyceraldehyde 3-phosphate.

<x-custom-btb-me data-me-id='1631' class='microExplainerHighlight'>Organic Chemistry</x-custom-btb-me>, Chapter 29.SE, Problem 22MP , additional homework tip  1

Concept introduction:

Reactions that make and break C-C-Bonds

Reactions that make and break carbon-carbon bonds form the basis of both degradative and biosynthetic metabolism.

The breakdown of glucose to CO2 involves give such cleavages where as its synthesis involves the reverse process such reactions, considered from the synthetic direction involve addition of a nucleophilic carbanion to an electrophilic carbon atom. The most common electrophilic carbon atoms in such reactions are the sp2 hybridized carbonyl atoms of aldehydes, ketones, etc. and CO2

Organic Chemistry, Chapter 29.SE, Problem 22MP , additional homework tip  2

Stabilized carbanions must be generated to add to these electrophilic centres. Three examples are the aldol condensation (catalyzed eg by aldolase) claisen ester condensation (citrate synthase) and the decarboxylation of β-keto acids. (isocitrate dehydrogenase and fatly acid synthase).

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Galactose can enter the glycolytic cycle but it must first react with ATP to form galactose-1-phosphate. Propose a mechanism for this reaction.
TPP is a coenzyme for transketolase, the enzyme that catalyzes the conversion of a ketopentose (xylulose5-phosphate) and an aldopentose (ribose-5-phosphate) to an aldotriose (glyceraldehyde-3-phosphate) and a ketoheptose (sedoheptulose-7-phosphate). Notice that the total number of carbons in the reactants and products is the same (5 + 5 = 3 + 7). Propose a mechanism for this reaction.
TPP is a coenzyme for transketolase, the enzyme that catalyzes the conversion of a ketopentose (xylulose- 5-phosphate) and an aldopentose (ribose-5-phosphate) to an aldotriose (glyceraldehyde-3-phosphate) anda ketoheptose (sedoheptulose-7-phosphate). Notice that the total number of carbons in the reactants and products is the same (5 + 5 = 3 + 7). Propose a mechanism for this reaction.

Chapter 29 Solutions

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