Question Details

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.

Options

A

B

C

D

Show Answer

Correct Answer :

Option B

Option B

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:
H2N-CH(CH2COOH)-COOH
It contains a side-chain carboxylic acid group (-CH2COOH).

• Phenylalanine has the chemical formula:
H2N-CH(CH2C6H5)-COOH
In phenylalanine methyl ester, the carboxyl group (-COOH) is replaced by a methyl ester group (-COOCH3):
H2N-CH(CH2C6H5)-COOCH3

3. Identify the Peptide Linkage:
In aspartame, the peptide bond (-CONH-) 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 (-CH2COOH) of the aspartyl residue remains free and does not participate in peptide bond formation.
• The linkage is represented by:
H2N-CH(CH2COOH)-CONH-CH(CH2C6H5)-COOCH3

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 -CH2COOH group free, and the C-terminal phenylalanine residue is esterified as -COOCH3.

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