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AMINO ACIDS

Topics
Introduction
Definition
Classification
Properties
EssentialAmino Acid
Selected Synthesis of Amino Acid
Definition
Amino acids are the simplest unit of a protein molecule
and they form the building blocks of protein structure.

An amino acid consists of a free NH2 and a free COOH


(carboxyl) group. Both are attached to the same carbon
atom. In the structure of the amino acid referred above,
‘R’ represents the groups other than the NH2 and COOH
groups. This may be aliphatic or heterocyclic group. In
glycine which is the simplest of the amino acids, ‘R’
represents ‘H’ atom.
In the steric configuration for serine,
the COOH is written on the top, while
the amino group is written to the left
in the case of L-serine and to the right
in the case of D-serine.
Classification
(A) Amino acids are classified in
different ways, among these, the
classification referring to the
number of carboxyl groups
present in the amino acids and
nature of structure.
◦ Mono amino mono carboxylic acids
◦ Mono amino dicarboxylic acids
◦ Diamino mono carboxylic acids
◦ Sulphur containing amino acids
B. Metabolism of Individual Amino Acids
1. Essential amino acids
They are indispensable and are required for
nutrition, promotion of normal growth and
maintenance of nitrogen balance.
◦Methionine
◦Arginine
◦Threonine
◦Valine
◦Isoleucine
◦Leucine
◦Phenylalanine
◦Lysine
◦Histidine
◦Tryptophan

II. Non Essential amino acid


Properties
Physical Properties
1. Amino acids are white crystalline substances.
2. Generally soluble in water & insoluble in organic
solvents.
3. High melting points, varies from 2000oC-3000oC or
even more.
4. They may be tasteless, sweet or bitter.
5. All amino acids except glycine are optically active.
6. They are amphoteric, react with both alkalies &
acids. They carry +ve charge in acids, but –ve
charge in alkaline solution. But they are electrically
neutral in certain reaction around neutrality.
Zwitterion Theory

According to this theory, amino acids possessing double charges (positive and negative) are called zwitterions.

Isoelectric point
◦ The PH at which amino acid has no tendency to move either to the positive or negative electrode is called its isoelectric point

Chemical Properties
The chemical properties of amino acids are
due to their amino groups and carboxyl
groups, so they classified as follows,
1. Reaction of amino acids due to amino
groups
2. Reaction of amino acids due to carboxyl
groups
(1) Reaction of amino acids due to
amino groups
Reaction with formaldehyde

Reaction of Glycine with Benzoic acid

Reaction with Nitrous acid


Reaction of Ninhydrin
Oxidative deamination of amino acid

The blue coloured compound Rheumann’s


purple formed as follows,
Reaction with I-Fluro-2, 4-
Dinitrobenzene (FDNB):

Reaction with carbon dioxide-


Siegfried’s carbamino reaction:
Formation of Diketopiperazines:

Chelation with metal ions:


◦ Heavy metals like Cu++, Hg++,
Mn++, Fe++, etc. form chelated
complexes with amino acids in which
both carboxyl & amino groups are
involved.
(2) Reaction of amino acids due to
carboxyl groups
Formation of Esters:

Decarboxylation-Formation of
Amine:
Formation of Amide:

Amino acid esters form amides when treated with


anhydrous or alcoholic ammonia
Selected Synthesis of
Amino Acid
 Amination of α–halogenated acids.
◦ An α -chloro- or bromo-acid is treated with concentrated ammonia,

◦ Gabriel’s phthalimide synthesis with α-halogeno-acids


•Aromatic aldehydes with
diketopiperazine
References
Fundamentals of Biochemistry for
Medical Students by Ambika
Shanmugam
Organic Chemistry Volume
II:Steriochemistry and the
Chemistry of Natural Products by
I.L.Finar
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