AMINO ACIDS

Dr. GOMA KATHAYAT

LECTURER
DEPARTMENT OF BIOCHEMISTRY
PROPERTIES OF AMINO ACIDS
A. Physical properties:
1. Solubility
Most of the amino acids are soluble in water; but
insoluble in organic solvents.

2. Melting points
All amino acids have melting point above 200°C.

3. Taste
Amino acids may be sweet ( Gly, Ala, Val), tasteless
(Leu) or bitter (Arg, Ile).
4. Optical properties:
• α carbon of amino acid is asymmetrical
because 4 different groups are attached, so it
shows optical isomerism /stereoisomer (D-
and L- isomers).

• All amino acid shows optical isomerism except

glycine.
D isomer L isomer
• Only L-amino acids are found in human
beings and also in proteins.

• Certain D-amino acids are found in the

antibiotics (Actinomycin-D, Valinomycin)
5. Amino acids as ampholytes:

• Amino acid contain both acidic (-COOH) and

basic (-NH2) groups. They can donate a
proton or accept a proton, hence regarded as
ampholytes.
Amino acid (general structure):
Amino Acid as acid:
R – COOH ↔ R – COO- + H+

Amino acid as base:

R – NH2 + H+ ↔ R – NH3+
Zwitterions:
Molecules that contain an equal number of
ionizable groups of opposite charge (both
positive and negative charge) and that
therefore bear no net charge.

Formation of zwitterions depend on pH of

the solution.
Isoelectric pH (pI):
The pH at which the molecule exists as a
zwitterion and carries no net charge.

At a particular pH:
Net charge = 0
SIGNIFICANCE OF PI

 At isoelectric pH amino acid doesn’t move

in electric field.

 Solubility and buffering capacity of amino

acid is minimum at isoelectric pH.
 If amino acid is dissolved in acidic medium
(lower than its pI) it becomes positive charge
(cation).

 Ifamino acid is dissolved in alkaline medium

(higher than its pI), it becomes negative charge
(anion).
pH = 1
Acidic + Cation

-
pH = 7 Zwitterion
+
P.I

-
pH = 12 Anion
Basic
 Isoelectric pH of any amino acid depends on
Dissociation constant [pK value] of functional
group of α carbon and side chain [R].
CALCULATION OF PI
 For monoamino monocarboxylic amino acid
pI value can be calculated by taking the average
pKa values corresponding to ionizable groups (pK of
α-COO- and pK of α-NH3+).

i.e. pI = pK1 (COO-) + pK2 (NH3+)

2
Glycine; pK1 (α-COO-) = 2.34, pK2 (α-NH3+) = 9.60;

pI of glycine = 2.34 + 9.60 = 5.97

2
CALCULATION OF PI CONT…
 For polyfunctional a.a (acidic or basic)
pI is calculated by taking average of pK of iso-ionic
species.
E.g Aspartic acid (acidic amino acid)

Aspartic acid; pK1(α-COO-) =2.1, pK2 (R-COO-)=3.9, pK3( α-NH3+) =

9.9
pI of aspartic acid=pK1+pK2/2
= 2.1+3.9/2 = 3.0
IONIZATION OF ASPARTIC ACID
CALCULATION OF PI CONT…
 Lysine (basic amino acid)

 pK1(α-COO-)=2.2, pK2 (α -NH3+)=9.2, pK3 (R-

NH3+)=10.8
pI of lysine = pK2+pK3/2
=9.2+10.8/2= 10
TITRATION OF AMINO ACIDS

Titration curves helps us in understanding different

ionic forms of amino acids.
TITRATION OF ALANINE

Alanine [α-carboxyl and α-amino groups]

At a low pH, both groups are protonated

[-COOH and NH3+]
TITRATION OF ALANINE CONT…

Dissociation of carboxyl group

As the pH of the solution is raised, –COOH
group of form I starts dissociating by donating a
proton [H+] to the medium

Resultant formation of carboxylate group [–

COO–], form II (The dipolar form of the
molecule)
TITRATION OF ALANINE CONT…
Form II – A zwitterion [An isoelectric form of
alanine, with the overall charge of zero]
TITRATION OF ALANINE CONT…

Dissociation of amino group

The second dissociable group of alanine is the
amino group [-NH3+]
TITRATION OF ALANINE CONT…
Release of a proton from a protonated amino
group of form II results in the fully de-
protonated form of alanine (-NH2), i.e., form III
TITRATION OF ALANINE CONT…

The pka of alanine

Each dissociable group of alanine has a pKa

-COOH: pK1
-NH3+: pK2
TITRATION CURVE OF ALANINE

The change in pH that occurs during the

addition of base to the fully protonated form
of alanine (form I) to produce the completely
deprotonated form (form III), via an
intermediate form (form II)
B. CHEMICAL PROPERTIES:

1. Reactions due to –COOH group

a. Decarboxylation: Amino acids undergo decarboxylation to
produce corresponding amines.

These amines are biologically important.

a. Histidine------- Histamine + CO2

b. Tyrosine-------- Tyramine + CO2
c. Tryptophan-----Tryptamine + CO2
d. Glutamate------GABA + CO2
b. Amide formation: The –COOH group of dicarboxylic
amino acids (other than α-carboxyl) can combine with
ammonia to form the corresponding amide. E.g

 Aspartic acid + NH3 Asparagine

Glutamic acid + NH3 Glutamine

2.Reactions due to amino (-NH2) group

a. Transamination: Transfer of an alpha amino group

from an amino acid to alpha keto acid to form a new amino
acid and alpha keto acid is a very important reaction in amino
acid metabolism
b. Oxidative deamination :

 Removal of alpha amino group from the amino acid

to form the corresponding keto acid and ammonia.

 Glutamic
acid is most common amino acid to
undergo oxidative deamination.
c. Formation of carbamino compound
Carbon dioxide adds to the alpha amino group of
amino acids to form carbamino compounds. This
reaction is important for transport of CO2 from
tissues to the lungs by hemoglobin (Hb).

Hb-NH2+CO2----Hb-NH-COOH (Carbamino –Hb)

3. Reactons due to side chains
a. Transmethylation
The methyl group of methionine, after activation,
may be transferred to an acceptor, which becomes
methylated.

Methionine+acceptor----- methylated acceptor +

Homocysteine
b. Ester formation by the OH group
 The hydroxy amino acids can form esters with
phosphoric acid.

 Serine and threonine residues of proteins are

involved in the formation of phosphoproteins.

 These hydroxyl group can form O-glycosidic bonds

with carbohydrate residues to form glycoproteins.
c. Reaction of the amide group:
 The amide groups of glutamine and asparagine can
form N-glycosidic bonds with carbohydrate residues
to form glycoproteins.

d. Reactions of SH group:
 Cysteine has a sulfhydryl (SH) group and it can form
a disulfide (S-S) bond with another cysteine residue
to form cystine.
THANK YOU…