Aspartame, an artificial sweetener, is a dipeptide aspartyl phenylalanine methyl ester. The structure of aspartame is
Structures of phenylalanine and aspartic acid are given below.
Correct Answer :
Solution :
The correct option is Option B.
Step-by-Step Explanation:
1. Understand the components of Aspartame:
Aspartame is an artificial sweetener chemically known as L-aspartyl-L-phenylalanine methyl ester. It is a dipeptide derivative composed of two amino acids:
• L-aspartic acid
• L-phenylalanine (esterified at its carboxyl terminal with methanol to form a methyl ester)
2. Structures of the starting materials (as shown in the question):
• Aspartic acid has the chemical formula:
It contains a side-chain carboxylic acid group ().
• Phenylalanine has the chemical formula:
In phenylalanine methyl ester, the carboxyl group () is replaced by a methyl ester group ():
3. Identify the Peptide Linkage:
In aspartame, the peptide bond () is formed specifically between the α-carboxyl group of aspartic acid and the α-amino group of phenylalanine methyl ester. This means:
• The side-chain carboxylic acid group () of the aspartyl residue remains free and does not participate in peptide bond formation.
• The linkage is represented by:
4. Matching with the Options:
• Option B correctly depicts the structure where the peptide bond is formed using the α-carboxyl carbon of aspartic acid, leaving the group free, and the C-terminal phenylalanine residue is esterified as .
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