Look at the open-chain form of D-mannose and draw the two glycosidic products that you expect to obtain by reacting D-mannose with methanol.
Ch.20 Carbohydrates
Chapter 20, Problem 62
Amylose (a form of starch) and cellulose are both polymers of glucose. What is the main structural difference between them? What roles do these two polymers have in nature?
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Amylose and cellulose are both polysaccharides made up of glucose monomers, but the key structural difference lies in the type of glycosidic bond connecting the glucose units. Amylose has α(1→4) glycosidic bonds, while cellulose has β(1→4) glycosidic bonds.
The α(1→4) glycosidic bonds in amylose result in a helical structure, which is more compact and suitable for energy storage. In contrast, the β(1→4) glycosidic bonds in cellulose create a linear, rigid structure that allows for the formation of strong hydrogen bonds between adjacent chains, giving cellulose its high tensile strength.
Amylose, as a component of starch, serves as an energy storage molecule in plants. It can be broken down by enzymes like amylase to release glucose for metabolic processes.
Cellulose, on the other hand, is a structural polysaccharide found in the cell walls of plants. Its rigidity and strength provide structural support to plant cells and contribute to the overall stability of the plant.
In summary, the main structural difference is the type of glycosidic bond (α vs. β), which leads to different roles: amylose for energy storage and cellulose for structural support in plants.

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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Polymers of Glucose
Amylose and cellulose are both polysaccharides made up of glucose monomers. Polymers are large molecules formed by repeating units, and in the case of these two substances, they consist of glucose linked together in different configurations. Understanding their polymeric nature is essential to grasp their structural and functional differences.
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Structural Differences
The main structural difference between amylose and cellulose lies in the type of glycosidic bonds that link the glucose units. Amylose consists of α(1→4) glycosidic bonds, resulting in a helical structure, while cellulose has β(1→4) glycosidic bonds, leading to a straight, rigid structure. This difference in bonding affects their physical properties and biological functions.
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Roles in Nature
Amylose primarily serves as an energy storage molecule in plants, allowing them to store glucose for later use. In contrast, cellulose provides structural support to plant cell walls, giving them rigidity and strength. These roles are crucial for plant survival and growth, highlighting the functional significance of these two polymers in nature.
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Related Practice
Textbook Question
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Draw a disaccharide of two cyclic mannose molecules attached by an α-1,4 glycosidic linkage. Explain why the glycosidic products in Problem 20.58 are not reducing sugars, but the product in this problem is a reducing sugar.
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Lactose and maltose are reducing disaccharides, but sucrose is a nonreducing disaccharide. Explain.
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How are amylose and amylopectin similar to each other, and how are they different from each other?
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Trehalose, a disaccharide found in the blood of insects, has the following structure. What simple sugars would you obtain on hydrolysis of trehalose? (Hint: Rotate one of the rings in your head or redraw it rotated.)
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Are the α and β forms of the disaccharide lactose enantiomers of each other? Why or why not?
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