Textbook Question
Write the equation for the final step in the catabolism of any fatty acid with an even number of carbons.
Ch.24 Lipid Metabolism
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
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Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
Chapter 24, Problem 47a
Show the products of each step in the fatty acid oxidation of hexanoic acid.
a. 
Verified step by step guidance1
Step 1: Understand the process of fatty acid oxidation (beta-oxidation). Beta-oxidation is a metabolic process where fatty acids are broken down in the mitochondria to generate acetyl-CoA, NADH, and FADH2. Each cycle of beta-oxidation removes a two-carbon unit from the fatty acid chain in the form of acetyl-CoA.
Step 2: Activate hexanoic acid (C6H12O2) by converting it into its CoA derivative. This involves the reaction of hexanoic acid with coenzyme A (CoA) in the presence of ATP, forming hexanoyl-CoA. The reaction can be represented as: .
Step 3: Perform the first step of beta-oxidation, which is the oxidation of hexanoyl-CoA. This step involves the removal of two hydrogen atoms from the beta and alpha carbons of the fatty acid chain, forming a double bond. The enzyme acyl-CoA dehydrogenase catalyzes this reaction, and FAD is reduced to FADH2.
Step 4: Hydrate the double bond formed in the previous step. The enzyme enoyl-CoA hydratase adds a molecule of water across the double bond, converting it into a hydroxyl group on the beta carbon and a single bond between the alpha and beta carbons.
Step 5: Continue the beta-oxidation cycle by oxidizing the hydroxyl group on the beta carbon to a keto group using the enzyme beta-hydroxyacyl-CoA dehydrogenase. NAD+ is reduced to NADH in this step. Finally, the beta-ketoacyl-CoA is cleaved by thiolase, releasing acetyl-CoA and a shortened fatty acyl-CoA (now with four carbons, butyryl-CoA). Repeat the cycle until the fatty acid is completely broken down into acetyl-CoA units.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Fatty Acid Oxidation
Fatty acid oxidation is a metabolic process where fatty acids are broken down to generate energy. This process occurs primarily in the mitochondria and involves several steps, including activation, transport into the mitochondria, and beta-oxidation, where fatty acids are converted into acetyl-CoA units. Each cycle of beta-oxidation shortens the fatty acid chain by two carbon atoms, producing NADH and FADH2, which are crucial for ATP production.
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Oxidation of Fatty Acids Concept 3
Hexanoic Acid
Hexanoic acid, also known as caprylic acid, is a medium-chain fatty acid with six carbon atoms. It is significant in metabolism because it can be rapidly oxidized for energy compared to long-chain fatty acids. Understanding its structure and properties is essential for analyzing its oxidation pathway, as the length of the carbon chain influences the enzymes and processes involved in its breakdown.
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Beta-Oxidation Pathway
The beta-oxidation pathway is a series of enzymatic reactions that degrade fatty acids into acetyl-CoA units. Each cycle of beta-oxidation involves four main steps: oxidation, hydration, another oxidation, and thiolysis. For hexanoic acid, this pathway will yield three cycles of beta-oxidation, producing two molecules of acetyl-CoA and generating reducing equivalents in the form of NADH and FADH2, which are vital for ATP synthesis in the electron transport chain.
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Related Practice
Textbook Question
Why is the stepwise oxidation of fatty acids called β oxidation?
Textbook Question
What causes acetone to be present in the breath of someone with uncontrolled diabetes?
Textbook Question
Arrange these following four molecules in increasing order of their biological energy content (per mole):
a. Sucrose
b. Myristic acid, CH3(CH2)12COOH
c. Glucose
d. Capric acid, CH3(CH2)8COOH
Textbook Question
How many molecules of acetyl-CoA result from complete catabolism of the following compounds?
a. Myristic acid, CH3(CH2)12COOH
Textbook Question
How many moles of ATP are produced by the complete oxidation of 1 mol of myristic acid?