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Chapter 4: Problem 15

The artificial sweeteners Equal and Nutrasweet contain aspartame, which has the structure: What are the two amino acids that are components of aspartame? What kind of bond links these amino acids? What do you suppose might happen if a solution of aspartame was heated for several hours at a pH near neutrality? Suppose you wanted to make hot chocolate sweetened only with aspartame, and you stored it in a thermos for several hours before drinking it. What might it taste like?

Short Answer

Expert verified
Aspartame, used in Equal and Nutrasweet, is composed of two amino acids, phenylalanine and aspartic acid, linked by a peptide bond. If a solution of aspartame is heated for several hours at a neutral pH, it undergoes hydrolysis, breaking down into its component amino acids. Thus, hot chocolate sweetened with aspartame and kept in a thermos might taste less sweet than if it were consumed immediately.

Step by step solution

01

Identification of Amino Acids in Aspartame

The two amino acids that make up aspartame are phenylalanine and aspartic acid.
02

Type of Bond Linking the Amino Acids

The bond that links these two amino acids in aspartame is a peptide bond, which is a type of covalent bond that is formed when the carboxyl group of one molecule reacts with the amino group of another molecule, releasing a molecule of water (H2O). This is also referred to as a dehydration synthesis.
03

Effect of Heating Aspartame at Neutral pH

When aspartame is heated for several hours at a pH near neutrality, it undergoes hydrolysis, a chemical reaction where a water molecule breaks the peptide bond. As a result, aspartame breaks down into its component amino acids, phenylalanine and aspartic acid, which can alter its sweetness.
04

Taste Prediction of Hot Chocolate Sweetened with Aspartame

If the hot chocolate is sweetened only with aspartame and stored in a thermos for several hours before drinking, the aspartame could lose its sweetness due to the hydrolysis reaction. Therefore, the hot chocolate might taste less sweet than originally intended.

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Most popular questions from this chapter

Although the other common amino acids are used as buffers, cysteine is rarely used for this purpose. Why?

Without consulting chapter figures, draw Fischer projection formulas for glycine, aspartate, leucine, isoleucine, methionine, and threonine.

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