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Ch.6 Carbohydrates Life's Sweet Molecules
Frost - General, Organic and Biological Chemistry 4th Edition
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
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 composed of N-acetylglucosamine units linked by β-1,4-glycosidic bonds, similar to the structure of cellulose, which is composed of glucose units linked by β-1,4-glycosidic bonds.
Amylose, on the other hand, is a polysaccharide composed of glucose units linked by α-1,4-glycosidic bonds, which are more easily broken down by human digestive enzymes such as amylase.
Human digestive enzymes, like amylase, are specialized to hydrolyze α-glycosidic bonds found in amylose and other starches, but they cannot efficiently break down β-glycosidic bonds found in cellulose and chitin.
Since chitin contains β-1,4-glycosidic bonds, similar to cellulose, the human digestive system lacks the enzymes necessary to break these bonds and convert chitin into its component sugars.
Therefore, if you eat a boiled shrimp without removing the shell, your body will not be able to break down the chitin in the shell into its component sugars, and it will pass through your digestive system largely undigested.

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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 unique structure provides strength and rigidity, making it a key component in the exoskeletons of arthropods like shrimp.
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Digestive Enzymes

Humans lack the specific enzymes required to break down chitin, such as chitinase. While we can digest polysaccharides like amylose and cellulose due to the presence of amylase and cellulase, respectively, the absence of chitinase means that chitin remains largely undigested in the human gastrointestinal tract.
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Comparison with Amylose and Cellulose

Amylose is a component of starch, composed of α(1→4) linked glucose units, making it digestible by human enzymes. In contrast, cellulose, like chitin, has β(1→4) linkages but is also indigestible for humans. This comparison highlights the structural differences that determine whether a polysaccharide can be broken down by human digestive systems.