Nitrogen Containing Compounds: Amino Acids

Nitrogen containing compounds: Amino
Acids
Protein, the term is derived from Greek word Proteios means “ primary” or
“holding first place” or “pre eminent” because Jons Jacob Berzelius, a Swedish
chemist, thought them to be most important of biological substances. And now we
know that proteins are fundamental structural and functional components of the
body. They are nitrogenous “macromolecules” composed of many amino acids.
Most proteins contain, in varying proportions, the same 20 L-α-amino acids. Many
specific proteins contain, in addition, L-α-amino acids derived from some of the
basic 20 amino acids by processes that occur after formation of the polypeptide
backbone. These unusual amino acids fulfill highly specific functions for the protein
and increase biologic diversity. This chapter considers the structures, physical
properties, stereochemistry, chemical properties and ionic equilibrium of the amino
acids. Also considered are methods for separation and the importance of water in
our life.
Amino acids are monomers of proteins 300 amino acid occurs in nature A
subset of only 20 constitute the monomeric units of a protein
Amino acids
Definition: an amino acid is an organic compound containing an amino group

and an acidic group (usually, but not always, a carboxylic acid). This description fits
a very large number of compounds, most of which are non-physiological. In
addition, many physiologically important amino acids are not used in proteins.
However, in biochemistry, the term “amino acid” generally refers to one of the 20
types of monomeric units most commonly used to construct proteins.
Common amino acids Has at least one codonin the genetic code Eg. Alanine,
glycine, cysteine
alanine
Derived amino acids Common amino acids gets altered after translation
process. Cystine, hydroxylysine, hydroxyproline
Cystine Hydroxylysine Hydroxyproline
Biomedical importance of amino acids
In health:
• Diet contains essential amino acids
• In the form of proteins amino acids perform a multitude of structural,

hormonal, catalytic functions.
• Participates in intracellular functions - nerve transmission, regulation of cell

growth, biosynthesis of porphyrins, purines, pyrimidines, urea, creatinine,
neurotransmitters
In disease
• Genetic defects in metabolism of amino acids results in inborn errors (Phenyl

ketonuria)
• Additional genetic disease can result from an impaired ability to transport

specific amino acids - leads to increased excretion of amino acids – aminoaciduria
• Inborn error of urea cycle

General Amino Acid Structure
Classification of Amino Acids
Based on structure amino acids can be divided into following groups
Aliphatic amino acids
Mono amino mono carboxylic acids
Simple amino acids – Glycine, Alanine
alanine
Branched chain amino acids - Valine, Leucine, Isoleucine
valine
Hydroxy amino acids - Serine, Threonine

Sulphur containing amino acids – Cysteine, Methionine
Amino acids with amide groups – Asparagine, Glutamine
asparagine
Mono amino dicarboxylic acids – Aspartic acid , Glutamic acid

aspartic acid
Dibasic mono carboxylic acids – Lysine, Arginine
arginine
Aromatic amino acids
phenylalanine tyrosine
Heterocyclic amino acids
Based on side chaine characters (polarities)
Non polar side chains

Alanine, Valine, Leucine, Isoleucine Methionine, Proline, Phenylalanine,
Tryptophan
Non ionic polar side chains
Glycine, Serine, Threonine, Cysteine, Tyrosine, Glutamine, Asparagine
Ionic polar side chains
Acidic amino acids
Aspartic acid, Glutamic acid
Basic amino acids
Lysine Arginine, Histidin
Classification based on nutritional significance
Essential amino acids - cannot be synthesized in our body Methionine,

Tryptophan, Threonine, Valine, Leucine, Isoleucine, Phenylalanine, Lysine
Semi essential amino acids - partially synthesized Histidine, Arginine
Non-essential amino acids - can be synthesized in our body Alanine, Aspartic

acid, Cysteine, Glutamic acid, Glycine, Proline, Serine, Asparagine, Glutamine,
Tyrosine
Properties of Amino acids
Physical properties
Solubility - colourless crystalline highly soluble in water, slightly soluble in
alcohol insoluble in ether. Soluble in dilute acids and bases
Melting point Very high, above 2000 C
Optical properties All amino acids except glycine exhibit optical activity
because of the asymmetry at the α carbon atom.
Chemical properties of Amino acids
The chemical properties of α-amino acids are determined by the presence of

functional groups with opposite properties - carboxyl (acidic) and amino (basic).
Amino acids interacting with acids and bases, that is, exhibit amphoteric properties.
The formation of zwitterion
In the crystalline state and in aqueous solutions of amino acids exist in the
form of bipolar ions (zwitterions).
α-amino acid zwitterion
Inner salt (zwitterion) is in two places opposite charges, and as it involves two
ion - as positive NH3+ group and a negative COO- groups. Therefore, aqueous
solutions of mono amino mono carboxylic acids is neutral.
Reactions due to carboxyl group
Exhibiting acidic properties, amino acids reacts with alkalis to form salts.
Sodium salt of
glucine aminoacetic acid
The carboxyl groups of amino acids may be esterified with alcohols
Reactions of the amino group
As bases, amino acids react with strong mineral acids, attaching proton.
hydrochloride of glycine
The reactions with the simultaneous participation of the two functional

groups
Under certain conditions, the carboxyl group of one amino acid molecule can
react with the amino group of another molecule. When this water molecule is
cleaved, and the amino acid residues are bound by a peptide bond.
Characteristic of peptide bond
Peptide bond has a partial double bond character

•There is no freedom of rotation about the bond that connects the C and N
atoms.
•All the four atoms lie in the same plane (Coplanar)
•This limited movement result in the existence of higher level of protein
structure
•A specific conformation is required for physiological activty.
•These favored conformations depend on factors such as hydrogen bonding,
Peptides are oligomers of amino acids formed by the condensation of an α

amino group of one amino acid with the α carboxyl group of another amino acid.
Dipeptide - Two amino acids
Tripeptide - Three amino acids
The polypeptides are very important for biological processes of living
organisms. For example, in brain was found peptides sleep, memory, anxiety, etc.
Such research can provide powerful new tools directed, rational action on the brain,
including those for the treatment of many mental illnesses.
Preparation of amino acid
1. Hydrolysis of proteins
Hydrolysis of proteins obtained are complex mixtures of amino acids.
However, there are a number of methods that allow obtain mixtures of these
individual pure amino acids.
2. Interaction of halogen derived carboxylic acids with excess of ammonia.
chloracetic acid aminoacetic acid
Sources:
http://www.public.iastate.edu/~duahn/teaching/Biomodulation%20and%20Protein/
Amino%20Acids%20and%20peptide%20bond.pdf
http://www.srmuniv.ac.in/sites/default/files/files/B3_PROTEINCHEMISTR
Y.pdf

Nitrogen Containing Compounds: Amino Acids

Uploaded by

Copyright:

Available Formats

Nitrogen Containing Compounds: Amino Acids

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Nitrogen Containing Compounds: Amino Acids

Uploaded by

Copyright:

Available Formats

Nitrogen containing compounds: Amino

Definition: an amino acid is an organic compound containing an amino group

Cystine Hydroxylysine Hydroxyproline

Biomedical importance of amino acids

• Diet contains essential amino acids

• In the form of proteins amino acids perform a multitude of structural,

• Participates in intracellular functions - nerve transmission, regulation of cell

• Genetic defects in metabolism of amino acids results in inborn errors (Phenyl

• Additional genetic disease can result from an impaired ability to transport

• Inborn error of urea cycle

Classification of Amino Acids

Based on structure amino acids can be divided into following groups

Aliphatic amino acids

Mono amino mono carboxylic acids

Simple amino acids – Glycine, Alanine

Branched chain amino acids - Valine, Leucine, Isoleucine

Hydroxy amino acids - Serine, Threonine

Amino acids with amide groups – Asparagine, Glutamine

Mono amino dicarboxylic acids – Aspartic acid , Glutamic acid

Dibasic mono carboxylic acids – Lysine, Arginine

Aromatic amino acids

Based on side chaine characters (polarities)

Non polar side chains

Non ionic polar side chains

Glycine, Serine, Threonine, Cysteine, Tyrosine, Glutamine, Asparagine

Ionic polar side chains

Acidic amino acids

Aspartic acid, Glutamic acid

Basic amino acids

Lysine Arginine, Histidin

Classification based on nutritional significance

Essential amino acids - cannot be synthesized in our body Methionine,

Semi essential amino acids - partially synthesized Histidine, Arginine

Non-essential amino acids - can be synthesized in our body Alanine, Aspartic

Melting point Very high, above 2000 C

Chemical properties of Amino acids

The chemical properties of α-amino acids are determined by the presence of

The formation of zwitterion

α-amino acid zwitterion

Reactions due to carboxyl group

Reactions of the amino group

The reactions with the simultaneous participation of the two functional

Peptide bond has a partial double bond character

Peptides are oligomers of amino acids formed by the condensation of an α

Preparation of amino acid

2. Interaction of halogen derived carboxylic acids with excess of ammonia.

chloracetic acid aminoacetic acid

You might also like