Textbook Question
How would you classify the link between the monosaccharides in cellobiose?
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Ch.20 Carbohydrates
McMurry8th EditionFundamentals of GOBISBN: 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
Chapter 20, Problem 22a
Consider the trisaccharide A, B, C shown in Problem 20.23.
a. Identify the hemiacetal and acetal linkages.
Verified step by step guidance1
Step 1: Understand the structure of a hemiacetal and an acetal. A hemiacetal contains a carbon atom bonded to one -OH group and one -OR group, while an acetal contains a carbon atom bonded to two -OR groups.
Step 2: Examine the structure of the trisaccharide provided in Problem 20.23.a. Identify the carbon atoms that are part of glycosidic linkages, as these are potential sites for acetal or hemiacetal formations.
Step 3: For each glycosidic linkage, determine whether the carbon atom involved is bonded to one -OH group and one -OR group (hemiacetal) or two -OR groups (acetal).
Step 4: Identify the anomeric carbon atoms in the monosaccharide units. The anomeric carbon is the carbon derived from the carbonyl group (C=O) of the sugar and is typically involved in forming glycosidic bonds.
Step 5: Label each linkage in the trisaccharide as either a hemiacetal or an acetal based on the bonding pattern of the anomeric carbon atoms identified in the previous steps.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hemiacetal Linkage
A hemiacetal linkage forms when an aldehyde reacts with an alcohol, resulting in a compound that contains both an alcohol and an ether functional group. In the context of carbohydrates, hemiacetals are typically formed when a monosaccharide's carbonyl group reacts with one of its hydroxyl groups, leading to a cyclic structure. This linkage is crucial for understanding the reactivity and stability of sugars.
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Cyclic Hemiacetals Concept 1
Acetal Linkage
An acetal linkage occurs when a hemiacetal reacts with another alcohol, resulting in a compound with two ether groups. In carbohydrates, acetal linkages are formed during the glycosidic bond formation between monosaccharides, which is essential for creating disaccharides and polysaccharides. This linkage is important for the structural integrity and function of complex carbohydrates.
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2:17Formation of Hemiacetals and Acetals Concept 2
Glycosidic Bond
A glycosidic bond is a type of covalent bond that connects two monosaccharides through an acetal linkage, specifically between the anomeric carbon of one sugar and a hydroxyl group of another. This bond is pivotal in carbohydrate chemistry as it determines the structure and properties of oligosaccharides and polysaccharides. Understanding glycosidic bonds is essential for analyzing the formation and breakdown of carbohydrates in biological systems.
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Related Practice
Textbook Question
During the digestion of starch from potatoes, the enzyme α-amylase catalyzes the hydrolysis of starch into maltose. Subsequently, the enzyme maltase catalyzes the hydrolysis of maltose into two glucose units. Write an equation (in words) for the enzymatic conversion of starch to glucose. Classify each of the carbohydrates in the equation as a disaccharide, monosaccharide, or polysaccharide.
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Textbook Question
Identify the following as diastereomers, enantiomers, and/or anomers.
(a) β-D-fructose and β-D-fructose
(b) D-galactose and L-galactose
(c) L-allose and D-glucose (both aldohexoses)
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Textbook Question
Consider the trisaccharide A, B, C shown in Problem 20.23.
c. State the numbers of the carbon atoms that form glycosidic linkages between monosaccharide A and monosaccharide B.
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Textbook Question
Hydrolysis of both glycosidic bonds in the following trisaccharide A, B, C yields three monosaccharides.
c. Draw the Fischer projections for the three monosaccharides.
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Textbook Question
Are one or more of the disaccharides maltose, lactose, cellobiose, and sucrose part of the trisaccharide in Problem 20.23? If so, identify which disaccharide and its location. (Hint: Look for an α-1,4 link, β-1,4 link, or 1,2 link, and then determine if the correct monosaccharides are present.)
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