Textbook Question
Isomaltose, a disaccharide formed during caramelization in cooking, contains two glucose units bonded ⍺(1→6). Draw the structure of isomaltose.
Ch.6 Carbohydrates Life's Sweet Molecules
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696
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Table of contents
- Ch.4 Introduction to Organic Compounds75
- Ch.5 Chemical Reactions19
- Ch.6 Carbohydrates Life's Sweet Molecules62
- Ch.7 States of Matter and Their Attractive Forces8
- Ch.8 Solution Chemistry Sugar and Water Do Mix4
- Ch.10 Proteins Workers of the Cell89
- Ch.11 Nucleic Acids Big Molecules with a Big Role69
- Ch.12 Food as Fuel An Overview of Metabolism65
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 3, Problem 80
The glycosidic bond in a disaccharide was determined to be α(1→6). Hydrolysis of the disaccharide produced one galactose and one fructose. Draw the structure of the disaccharide.
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Understand the glycosidic bond notation: The α (1→6) bond indicates that the glycosidic linkage connects the anomeric carbon (carbon 1) of one sugar to the carbon 6 of another sugar, and the bond is in the alpha configuration (the -OH group on the anomeric carbon is pointing downward relative to the ring).
Identify the monosaccharides involved: The problem states that hydrolysis of the disaccharide produces galactose and fructose. This means these two monosaccharides are linked via the α (1→6) glycosidic bond.
Draw the structure of galactose: Galactose is a hexose sugar with the formula C₆H₁₂O₆. It is typically drawn in its cyclic form as a pyranose ring. Ensure the anomeric carbon (carbon 1) has the -OH group in the alpha configuration (pointing downward).
Draw the structure of fructose: Fructose is a hexose sugar with the formula C₆H₁₂O₆. It is typically drawn in its cyclic form as a furanose ring. Identify carbon 6, which will be involved in the glycosidic bond.
Connect the two structures: Link the anomeric carbon (carbon 1) of galactose to carbon 6 of fructose using the α (1→6) glycosidic bond. Ensure the bond is drawn clearly to reflect the alpha configuration and the correct carbons involved in the linkage.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Glycosidic Bond
A glycosidic bond is a type of covalent bond that connects a carbohydrate (sugar) molecule to another group, which can also be a carbohydrate. In disaccharides, this bond forms between the anomeric carbon of one sugar and a hydroxyl group of another, determining the structure and properties of the resulting molecule. The notation α (1→6) indicates the specific carbons involved in the bond formation, influencing the disaccharide's characteristics.
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Disaccharide Structure
A disaccharide is a carbohydrate composed of two monosaccharide units linked by a glycosidic bond. The specific arrangement of these units and the type of glycosidic bond (e.g., α or β) determine the disaccharide's properties and how it is metabolized. In this case, the disaccharide formed from galactose and fructose is crucial for understanding its structure and function.
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Hydrolysis Reaction
Hydrolysis is a chemical reaction that involves the breaking of a bond in a molecule using water. In the context of disaccharides, hydrolysis results in the separation of the two monosaccharide units, allowing for their individual identification. This reaction is essential for understanding how disaccharides are broken down in biological systems, providing energy and building blocks for more complex carbohydrates.
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Related Practice
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Our bodies cannot digest cellulose because we lack the enzyme cellulase. Why is cellulose an important part of a healthy diet if we cannot digest it?
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Will the following carbohydrates produce a positive Benedict’s test?
b. lactose
Textbook Question
Glycogen and amylopectin are both branched polymers of glucose. Read the descriptions of each in Section 6.6. Which molecule has a more compact structure? Explain.
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The shell of a shrimp is composed of chitin. If you eat a boiled shrimp without removing the shell, will your body break the shell down into its component sugars? Explain. (Hint: Compare chitin’s structure to that of amylose and cellulose.)
Textbook Question
Draw the product of the following 1→4 condensation and name the glycosidic bond: