Amino Acids and Proteins S-2

Chemistry Sem VI Paper-I Amino acids and Proteins
Session 2: synthesis of amino acids from Gabriel phthalimide

synthesis, Strecker’s synthesis, ninhydrin reaction, Peptides:
definition
Synthesis of α-Amino Acids

A variety of methods have been developed for the synthesis of a-amino acids. Here we
describe two methods that are based on reactions we have studied before. In “The Chemistry
of . . . Asymmetric Syntheses of Amino Acids” (WileyPLUS) we show methods to prepare a-
amino acids in optically active form. Asymmetric synthesis is an important goal in a-amino
acid synthesis due to the biological activity of the natural enantiomeric forms of a-amino
acids, and due to the commercial relevance of productsbmade by these routes.
From Potassium Phthalimide: Gabriel synthesis

This method, a modification of the Gabriel synthesis of amines, uses potassium
phthalimide and diethyl α-bromomalonate to prepare an imido malonic ester. The example
shown is a synthesis of methionine:
The Strecker Synthesis

Treating an aldehyde with ammonia and hydrogen cyanide produces an α-aminonitrile.
Hydrolysis of the nitrile group of the α-aminonitrile converts the latter to an α-amino acid.
This synthesis is called the Strecker synthesis:
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Digital Learning-DCE Karnatak University
Mechanism:
The first step of this synthesis probably involves the initial formation of an imine from the
aldehyde and ammonia followed by the addition of hydrogen cyanide.
Polypeptides and Proteins

Amino acids are polymerized in living systems by enzymes that form amide linkages
from the amino group of one amino acid to the carboxyl group of another.
A molecule formed by joining amino acids together is called a peptide, and the
amide linkages in them are called peptide bonds or peptide linkages. Each amino
acid in the peptide is called an amino acid residue.
Peptides that contain 2, 3, a few (3–10), or many amino acids are called dipeptides,
tripeptides, oligopeptides, and polypeptides, respectively. Proteins are polypeptides
consisting of one or more polypeptide chains.
Polypeptides are linear polymers. One end of a polypeptide chain terminates in an

amino acid residue that has a free NH3 group; the other terminates in an amino acid residue
with a free CO2 group. These two groups are called the N-terminal and the C-terminal
residues, respectively:
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By convention, we write peptide and protein structures with the N-terminal amino acid
residue on the left and the C-terminal residue on the right:
The tripeptide glycylvalylphenylalanine has the following structural formula:
Separation of Amino Acids: Ninhydrin reaction

Electrophoresis
A mixture of amino acids can be separated by several different techniques.
Electrophoresis separates amino acids on the basis of their pI values. A few drops of a solution
of an amino acid mixture are applied to the middle of a piece of filter paper or to a gel. When
the paper or the gel is placed in a buffered solution between two electrodes and an electric
field is applied, an amino acid with a pI greater than the pH of the solution will have an overall
positive charge and will migrate toward the cathode (the negative electrode). The farther the
amino acid’s pI is from the pH of the buffer, the more positive the amino acid will be and the
farther it will migrate toward the cathode in a given amount of time. An amino acid with a pI
less than the pH of the buffer will have an overall negative charge and will migrate toward the
anode (the positive electrode). If two molecules have the same charge, the larger one will
move more slowly during electrophoresis because the same charge has to move a greater
mass.
Since amino acids are colorless, how can we detect that they have been separated?
When amino acids are heated with ninhydrin, they form a colored product. After
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electrophoretic separation of the amino acids, the filter paper is sprayed with ninhydrin and
dried in a warm oven. Most amino acids form a purple product. The number of different kinds
of amino acids in the mixture is determined by the number of colored spots on the filter paper
(Figure 23.1). The individual amino acids are identified by their location on the paper
compared with a standard.
The mechanism for formation of the colored product is as shown, omitting the
mechanisms for the steps involving dehydration, imine formation, and imine hydrolysis.
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Chemistry Sem VI Paper-I Amino acids and Proteins

Session 2: synthesis of amino acids from Gabriel phthalimide

Synthesis of α-Amino Acids

From Potassium Phthalimide: Gabriel synthesis

The Strecker Synthesis

Polypeptides and Proteins

Polypeptides are linear polymers. One end of a polypeptide chain terminates in an

The tripeptide glycylvalylphenylalanine has the following structural formula:

Separation of Amino Acids: Ninhydrin reaction

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