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Ch.6 Carbohydrates–Life’s Sweet Molecules
Chapter 3, Problem 83

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.)

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Chitin is a polysaccharide, similar to cellulose and amylose, composed of repeating units of N-acetylglucosamine, a derivative of glucose.
Amylose is a component of starch and is made up of α-D-glucose units linked by α(1→4) glycosidic bonds, which are easily broken down by human digestive enzymes like amylase.
Cellulose, like chitin, is composed of β-D-glucose units, but linked by β(1→4) glycosidic bonds, which human digestive enzymes cannot break down.
Chitin's structure is similar to cellulose, with β(1→4) glycosidic bonds, but it also has an acetylated amino group, making it even more resistant to digestion.
Since humans lack the enzyme to break β(1→4) bonds in chitin, the shell of the shrimp will not be broken down into its component sugars in the human digestive system.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Chitin Structure

Chitin is a long-chain polymer of N-acetylglucosamine, a derivative of glucose. Its structure is similar to that of cellulose, featuring a linear arrangement of sugar molecules linked by β(1→4) glycosidic bonds. This structural configuration makes chitin rigid and resistant to degradation by most enzymes found in the human digestive system.
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Digestive Enzymes

Human digestive enzymes, such as amylase, are designed to break down starches like amylose, which consists of α(1→4) glycosidic bonds. However, humans lack the necessary enzymes to effectively break down chitin and cellulose, which require specific enzymes like chitinase that humans do not produce. This inability means that chitin remains largely intact during digestion.
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Comparison with Amylose and Cellulose

Amylose is a polysaccharide made of α-glucose units, while cellulose and chitin are composed of β-glucose and N-acetylglucosamine units, respectively. The difference in glycosidic bond types (α vs. β) is crucial, as it determines the digestibility of these polysaccharides. While amylose can be broken down by human enzymes, chitin's β-linkages render it indigestible, leading to its passage through the digestive system without being broken down.
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