AMINO ACIDS CHEMISTRY

Nagi Mohammed Alfatih

MBBS, MSc

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Introduction :
 Amino acids are the building blocks of
proteins ,

 There are about 300 naturally occurring

amino acid , only 20 of them involve in
protein synthesis = standard amino
acids

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 Definition of amino acids
 amino acids are organic compound in
which a carboxyl (-COOH) & an amino (-
NH3+) groups are attached to the same
carbon.= Alpha carbon

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Functions of Amino acids
1. They are the building blocks of
proteins.

2. Precursors for non protein specialized

products

3. Potential source of energy.

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 Amino acids : Nomenclature

• Each of the 20 (standard) amino acids

has:
– Full name
– 3 letter abbreviation
– 1 letter symbol

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 Amino acids: Nomenclature
Name 3 letter Symbol

Glycine Gly G
Alanine Ala A
Valine Val V
Leucine Leu L
Isoleucine Ile I
Serine Ser S
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 Amino acids: Nomenclature
Name 3 Letter Symbol

Threonine Thr T
Tyrosine Tyr Y
Cysteine Cys C
Methionine Met M
Aspartate Asp D
Asparagine Asn N
Glutamate Glu E
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 Amino acids: Nomenclature
Name 3 Letter Symbol

Glutamine Gln Q
Arginine Arg R
Lysine Lys K
Histidine His H
Phenylalanine Phe F
Tryptophan Trp W
Proline Pro P
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 Amino acids: Nomenclature
A C D E G

F H I K L

M N P Q R

S T V W Y

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 Amino acids: Structure

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 Classification of amino acid
 HOW DO WE CLASSIFY AMINO ACIDS ?

There are multiple ways of classification

of amino acids
[1] Chemical classification
[2] Nutritional classification
[3] Metabolic classification

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Classification of amino acid

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Classification of amino acid
According to the chemistry of the side chains
1. Non polar aliphatic.
2. Hydroxyl containing.
3. Sulfur-containing.
4. Acidic.
5. Basic.
6. Amides.
7. Aromatic.
8. Imino acid.
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Classification of amino acid
1. Non polar aliphatic:
i.e. R group form open chains
• Glycine. (small).
• Alanine. (small).
• Valine. (branched).
• Leucine. (branched).
• Isoleucine. (branched).
• Methionine. (Sulphur containing ).

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Classification of amino acid
2. Hydroxyl containing:
Their side chain contains –OH:
• Serine.
• Threonine.
• Tyrosine.

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Classification of amino acid
3. Sulfur-containing:
• The side chain contains a sulfur atom (S).
• Cysteine.
• Methionine.

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Classification of amino acid
4. Amides of acidic amino acids:
• The side chain contains (-COO-) or (-NH2)
• Asparagine.
• Glutamine.

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Classification of amino acid
5. Acidic amino acids:
• The side chain contains (-COO-) or (-NH2)
• Aspartic acid. D
• Aspartate
• Glutamic acid. E
• Glutamate

• DE
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Classification of amino acid
6. Basic amino acids :
• The side chain contains basic groups. Positive charged
• Arginine R
• Lysine K
• Histidine H (imidazole)

• HKR
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Classification of amino acid
7. Aromatic:
• The side chain contains an aromatic ring.
• Phenylalanine.
• Tyrosine.
• Tryptophan.

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Classification of amino acid

7. Imino acid:

• Proline.

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 Classification by solubility

• There are two broad classes of amino acids

based upon whether the R-group is
1. Hydrophobic
2. Hydrophilic.

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 The hydrophobic amino acids

The hydrophobic amino acids tend to repel

the aqueous environment and, therefore,
reside predominantly in the interior of
proteins and transmembrane regions.

The side chain of this class of amino acids

does not ionize nor participate in the
formation of H-bonds.

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 The hydrophilic amino acids
The hydrophilic amino acids tend to interact
with the aqueous environment; polar or
charged side chain.
They are often involved in the formation of
H-bonds
They are predominantly found on the
exterior surfaces of proteins or in the
reactive centers of enzymes
Involve in protein- protein interaction
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 Amino acids:
Nutritional classification
• Humans & higher animals can not
synthesize 10 amino acids in adequate
amount.
• Tshese 10 amino acid must be taken in
the diet.
i.e. Nutritionally-essential

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 Amino acids:
Nutritional classification

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Nutritionally-essential amino acids

W L M T F K R V I H

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 Amino acids:
Metabolic classification

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Amino acids: Polymers

Oligopeptides – <10 amino

acids

Polypeptides – 10-50 amino

acids

Proteins – 50-up to 1000s

amino acids
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 Peptide Bond

 it is a covalent bond that joins two

amino acids.

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 Peptide Bond

Peptide Bond is formed between the

α-carboxyl group of one amino acid and
the α-amino group of a second amino
acid with removal of one mol of H₂O.

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Peptide Bond

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Peptide Bond: Characteristics
[1] single bond
It has a partial double bond
character (resonance).
[2] Stronger than hydrogen bond
[3] Rigid & planar.
[4] Trans-configuration.
[5] Polar uncharged.

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Peptide: Definition

• “A polymer of two or
more ( less than 50)
amino acids linked by
peptide bond”.

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Protein: Definition
• “Apolymer of amino acids
(more than 50), linked by
peptide bond”.

Insulin is the smallest protein

51 AA.
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 Any Questions

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 Any Comment

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 Thank You

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