Aspartame, which is commonly known as Nutrasweet, contains the following dipeptide:


Screenshot 2024 01 28 130654

Screenshot 2024 01 28 130654

Step 1 of 2

Given data: Aspartame, which is commonly known as NutraSweet.

 

Find: a. what are the amino acids in Aspartame

  1. Give the three letter abbreviation of the N-terminal amino acid
  2. Circle the peptide bond.
  3. Draw the structure of the isomer of this dipeptide where the C-terminal and N-terminal amino acids are switched.

Explanation:

Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet.

 

Step 2 of 2

  1. Amino acids in aspartame:

Aspartame is composed of two amino acids: aspartic acid and phenylalanine.

 

+–Aspartic acidPhenylalanine.

 

  1. Three-letter abbreviation of the N-terminal amino acid:

Aspartic acid is abbreviated as Asp.

 

  1. Circle the peptide bond: The peptide bond is the covalent bond formed between the carboxyl group of one amino acid and the amino group of another amino acid. In aspartame, the peptide bond is between the carbonyl carbon of aspartic acid and the nitrogen of phenylalanine. I can’t physically circle it, but it’s represented as follows:

-+-Peptide bond

  1. Structure of the isomer with switched N and C terminals: The isomer of the dipeptide where the N-terminal and C-terminal amino acids are switched would be the reverse sequence of the original dipeptide. Therefore, the isomer would be Phe−Asp.

This structure shows the peptide bond between phenylalanine (Phe) and aspartic acid (Asp).

-+-PhenylalanineAspartic acid

 

Explanation:

Hence using the structure of Aspartame, we found the bonds and switch the terminal groups.

 

Final solution

In summary,

 

  1. Aspartame is composed of two amino acids: aspartic acid and phenylalanine.
  2. Aspartic acid is abbreviated as Asp.
  3. The peptide bond is the covalent bond formed between the carboxyl group of one amino acid and the amino group of another amino acid.
  4. The isomer would be Phe−Asp.

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