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Amino Acids

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3 views

Amino Acids

Uploaded by

morsalinredoy420
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Amino acids

Amino Acids
• Amino acids are organic acids that contain NH2
group.
• They are the structural units of proteins and are
obtained from them by hydrolysis.
• The general formula of any amino acid is as follows:
O
H2N CH C OH
R

• All these amino acids are alpha-amino acids and the


metabolizible form of them are L-amino acids.
Alpha-amino acid means that the amino group is
attached to the -carbon atom,
O
The general formula of any amino
H2Nacid
CH is : C OH
R
• Non polar R group containing 8 amino acids are:
• 1.Alanine( Ala ) 2.Leucine (leu ) 3.Proline(pro) 4.Valine(Val)
5.Isoleucine(Ile) 6.Phenylalanine( Phe ) 7.Tryptophan(Try)
8.Methionine (Met)
• Polar R group containing 7 amino acids are:
• 1.Glycine (Gly) 2.Serine (Ser) 3.Cysteine( Cys ) 4.Tyrosine(Tyr)
5. Threonine( Thr ) 6.Asparagine (Asn) 7.Glutamine (Gln)
• Negative charged R group containing two amino acids are:
• 1.Asparatic acid (Asp) 2. Glutamic acid (Glu)
• Positive charged R group containing amino acids are:
• 1.Lysine (Lys) 2.Arginine (Arg) 3.Histidine (His)
Properties of amino acids:
The amino acids differ in their physicochemical properties
which ultimately determine the characteristic of proteins.
A. Physical properties
1. Solubility : Most of the amino acids are usually soluble
in water and insoluble in organic solvents.

2. Melting points:
Amino acids generally melt at higher temperatures often
above 200.C.
3. Taste:
Amino acids may be sweet (gly,Ala, Val), tasteless (Leu) or
bitter (Arg, lle).Monosodium glutamate (MSG; ajinomoto) is
used as a flavoring agent in food industry, and in Chinese
foods to increase taste and flavor.
In someone intolerant to MSG, Chinese restaurant
syndrome (brief and reversible flu like symptoms) is
observed.
4. Optical properties:
All the amino acids except glycine possess optical isomers
due to the presence of asymmetric carbon atom.
Some amino acids also have a second asymmetric carbon
e.g. isoleucine, threonine.
5. Amino acids as ampholytes :
Amino acids contain both acidic (-COOH) and basic(-NH2)
groups. They can donate a proton or accept a proton, hence
amino acids can act as acid and base; are regarded as
ampholytes. Substances having this two-way property are
amphoteric which comes from Greek ‘amphi’ means both.

Zwitterion or dipolar ion : The name zwitter is derived from


the German word means hybrid. Zwitterion (or dipolar
ion) is a hybrid molecule containing positive and negative
ionic groups. The amino acids rarely exist in a neutral form
with free carboxylic (-COOH) and free amino(-NH2) groups.
In strongly acidic pH (low pH),the amino acid is positively
charged (cation) while in strongly alkaline pH (high pH), it is
negatively charged( anion).
As a base As a acid
Zwitterio
n
Each amino acid has a characteristic pH (e.g. leucine, pH
6.0) at which it carries both positive and negative charges
and exists as zwitterion .

Isoelectric pH (symbol pl ) is defined as the pH at which a


molecule exists as a zwitterion or dipolar ion and carries
no net charge. Thus, the molecule is electrically neutral .

6. Absorption of ultraviolet light:

Aromatic amino acids (tryptophan, tyrosine and phenylalanine)


can absorb ultraviolet light.
Classification of Amino Acids
Chemical classification:
Based upon the number of amino groups or
carboxyl groups in the amino acid ,amino
acids are divided into three groups:

1. Neutral amino acids (mono-amino, mono-


carboxylic).
2. Acidic amino acids (mono-amino,
dicarboxylic).
3. Basic amino acids (diamino, mono-carboxylic).
A) Neutral amino acids
• They contain one amino group and one carboxyl
group and the R group is aliphatic chain. They
are following 5 amino acids .
1-Aliphatic amino acids: e.g.,
2. Hydroxy amino acids: e.g.,
Serine are threonine are hydroxyl group
containing amino acids.

O O
H2N CH C OH H2N CH C OH
CH2 CH OH
OH CH3
Serine Threonine
3. Aromatic amino acids: e.g.,
• Phenylalanine, Tryptophan and tyrosine are aromatic ring
containing amino acids.
• Tyrosine is synthesized from phenyl alanine and both give
hormones- triiodothyronine and thyroxin, adrenaline and
noradrenaline.
• Melanin pigment and cresol ,phenol in the body, e.g.,
4-Sulfur-containing amino acids: e.g.,
• Cysteine gives cystine and its SH group is
very essential in activity of many proteins
particularly the active sites of enzymes.

O O O
H2N CH C OH H2N CH C OH H2N CH C OH
CH2 CH2 CH2
SH S CH2
Cysteine S S
CH2 CH3
H2N CH C OH
Methionine
CystineO
5-Heterocyclic amino acids: e.g.,
• Histidine gives histamine a very important inflammatory
mediator.
• Proline gives hydroxyproline that is essential for collagen
cross-linking.
• Tryptophan gives nicotinic acid, melatonin, serotonin and
indican in the body.

O O
H2N CH C OH O O
H2N CH C OH
C OH C OH
CH2 CH2
CH CH
N CH2 CH2
HN HN HN
NH CH2 CHOH
CH2 CH2
imidazole group indole group
Histidine Tryptophan Proline Hydroxyproline
B) Acidic amino acids
• They contain 2 carboxyl groups and one amino
group, e.g., glutamic acid and asparatic acid.
• These acidic amino acids can occur in the tissue in
the form of amides, e.g., glutamic acid  glutamine
and asparatic acid  asparagine.
C) Basic amino acids
• They contain 2 or more amino groups and one carboxyl group,
e.g., glutamine, asparagine , Arginine, Lysine and Histidine
Nutritional Classification of Amino Acids

• Proteins are required for their amino acids content.


Not all 20 a.as are required for body’s protein
synthesis. Body can synthesis some a.as from basic
element carbon, hydrogen, nitrogen etc. Body can not
synthesis their own protein without some a.as which
must be available and supplied on diet. According to
requirement of Body, a.as are two types:

• Essential amino acids


• Nonessential amino acids.
Essential or indispensable amino acids:
• The amino acids which body can not synthesize from their own
precursors and which must be supplied on diet ,otherwise their
deficiency will lead a nutrition deficiency disease that affect both
growth and health are called essential amino acids.
• Adult require eight essential amino acids in amount 1/2g/dl to 2
g/dl. They are isoleucine, leucine, lysine, methionine,
phenylalanine, threonine, tryptophan and valine .

• Infant and growing children require 10 amino acids . The extra two
are arginine and histidine . These two amino acids are called semi
essential amino acids.
Nonessential or Dispensable Amino acids :

• The amino acids which body can synthesize from their


own precursors without supple on diets and their
deficiency on diet does not affect the growth or the
health are called nonessential amino acids.
• The body can synthesize about 10 amino acids to
meet their biological needs hence they need not be
consumed in the diet.
• They are alanine ,serine ,cysteine , glutamate
,aspartate, glycine, aspartic acid , glutamic acid
,proline and asparagine.
Ninhydrin Test:
Ninhydrin reaction is chemical reaction used to
detect existence of amino acids.
Ninhydrin (triketohydrindene hydrate) is an
oxidizing agent which leads to the oxidative
deamination of alpha-amino groups. The α-amino
acids react with ninhydrin to form a purple, blue
or pink colour complex( Ruhemann's purple).

Amino acid + Ninhydrin → Keto acid


+NH3+CO2+Hydrindantin
Hydrindantin+ NH3+ Ninhydrin → Ruhemann's
purple

Ninhydrin reaction is effectively used for the


quantitative determination of amino acids and
proteins. (Note : Proline and hydroxyproline give
yellow colour with ninhydrin).
Amino acids useful as drugs:

There are certain non-standard amino acids that


are used as drugs.

 D-Penicillamine (D- dimethylglycine), a


metabolite of penicillin, is employed in the
chelation therapy of Wilson's disease. This is
possible since D –penicillamine can effectively
chelate copper.

 N- Acetylcysteine is used in cystic fibrosis, and


chronic renal
insufficiency, as it can function as an
antioxidant.

 Gabapentin (ɣ- aminobutyrate linked to


cyclohexane) is used as an anticonvulsant.

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