Textbook Question
The aldaric acid of D-glucose forms two five-membered-ring lactones. Draw their structures.
Ch. 20 - The Organic Chemistry of Carbohydrates
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 21, Problem 55
Hyaluronic acid, a component of connective tissue, is the fluid that lubricates joints. It is a polymer of alternating N-acetyl-D-glucosamine and D-glucuronic acid subunits joined by β-1,3′-glycosidic linkages. Draw a short segment of hyaluronic acid.
Verified step by step guidance1
Understand the structure of hyaluronic acid: It is a polymer made up of alternating N-acetyl-D-glucosamine and D-glucuronic acid subunits. These subunits are connected by β-1,3-glycosidic linkages.
Start by drawing the structure of N-acetyl-D-glucosamine. This is a glucose derivative where the hydroxyl group on carbon 2 (C2) is replaced by an acetamido group (-NHCOCH₃). Ensure the stereochemistry matches the D-configuration.
Next, draw the structure of D-glucuronic acid. This is a glucose derivative where the hydroxyl group on carbon 6 (C6) is oxidized to a carboxylic acid (-COOH). Again, ensure the stereochemistry matches the D-configuration.
Connect the two subunits using a β-1,3-glycosidic bond. This means the anomeric carbon (C1) of N-acetyl-D-glucosamine is linked to the hydroxyl group on carbon 3 (C3) of D-glucuronic acid. The β-configuration indicates that the glycosidic bond is above the plane of the sugar ring.
Repeat the alternating pattern of N-acetyl-D-glucosamine and D-glucuronic acid subunits to create a short segment of the polymer. Ensure that each pair of subunits is connected by a β-1,3-glycosidic bond, and verify the stereochemistry of each linkage.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Polymers
Polymers are large molecules composed of repeating structural units called monomers, which are covalently bonded together. In the case of hyaluronic acid, the monomers are N-acetyl-d-glucosamine and d-glucuronic acid. Understanding the structure and properties of polymers is essential for grasping how they function in biological systems, such as providing lubrication in joints.
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Introduction to Polymers Example 2
Glycosidic Linkages
Glycosidic linkages are covalent bonds that connect carbohydrate molecules through a reaction between a hydroxyl group of one sugar and the anomeric carbon of another. In hyaluronic acid, the beta-1,3′-glycosidic linkages specifically refer to the orientation and type of bond formed between the sugar units, which influences the polymer's stability and biological function.
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Connective Tissue
Connective tissue is a type of biological tissue that supports, binds together, and protects other tissues and organs in the body. It is characterized by a diverse composition of cells and extracellular matrix, including proteins and polysaccharides like hyaluronic acid. Understanding the role of connective tissue is crucial for appreciating how substances like hyaluronic acid contribute to joint lubrication and overall tissue health.
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01:41Different atoms or different connectivity.
Related Practice
Textbook Question
How many aldaric acids are obtained from the 16 aldohexoses?
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Textbook Question
Draw the mechanism for the interconversion of α-D-glucose and β-D-glucose in dilute HCl.
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Textbook Question
A hexose is obtained when the residue of a shrub Sterculia setigeria undergoes acid-catalyzed hydrolysis. Identify the hexose from the following experimental information: it undergoes mutarotation; it does not react with Br2; and D-galactonic acid and D-talonic acid are formed when it reacts with Tollens’ reagent.
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Textbook Question
A D-aldopentose is oxidized by nitric acid to an optically active aldaric acid. A Wohl degradation of the aldopentose leads to a monosaccharide that is oxidized by nitric acid to an optically inactive aldaric acid. Identify the D-aldopentose.
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Textbook Question
Draw the mechanism for the formation of β-lactose from ⍺-D-galactose and β-D-glucose in dilute HCl.
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