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CHAPTER 19 : AMINO ACIDS

19.1 Introduction to amino acids


Learning Outcomes:
(a)Draw the general structure of amino
acid.
(b)Name a given amino acid according to the
IUPAC nomenclature.
(c)Define the terms zwitterion and isoelectric
point, pI.
(d)Draw the structures of a given amino acid
i. in acidic medium
ii. in basic medium
iii. at pI

19.1 Introduction to amino acids


Amino acid: a compound that contains both an
amino group, -NH2 and a carboxyl group, -COOH

-amino acid: an amino acid in which the amino


group is on the carbon adjacent to the carboxyl
group

CH3CH2CHCOOH
NH2
The -carbon is the carbon atom next to the carboxyl group.

H
NH2

COOH

R
General structure of -amino acid

20 amino acids
Name
Glycine
Gly
Alanine
Ala

Valine
Val

Structure
H2N

CH

COOH

H2N

CH

COOH

CH3
H2N

CH

COOH

CHCH3
CH3

Name
Leucine
Leu

Structure
H2N

CH

COOH

CH2 CHCH3
CH3

Isoleucine
Ile

H2N

CH

COOH

CHCH2CH3
CH3

Serine
Ser

H2N

CH

COOH

CH2OH

Name
Theonine
Thr

Structure
H2N

CH

COOH

CHOH
CH3

Cysteine
Cys

Methionine
Met

H2N

CH

COOH

CH2SH
H2N

CH

COOH

CH2 CH2SCH3

Name
Aspartic
acid
Asp

Structure
H2N

Asparagine
Asn

COOH

CH2COOH

H2N
Glutamic
acid
Glu

CH

CH

COOH

CH2 CH2COOH

H2N

CH

COOH

CH2CNH2
O

Name
Glutamine
Gln

Structure
H2N

CH

COOH

CH2CH2CNH2
O

Arginine
Lysine

H2N

CH

COOH

(CH2)3NHCNH2
NH

Phenylalani
H2N
ne
Phe

CH

COOH

CH2CH2CH2CH2NH2

Name
Tyrosine
Tyr

Proline
Pro

Structure
H2N

CH

COOH

CH2

HN
CH2

CH
CH2

CH2

OH

COOH

Name
Tryptophan
Trp

Structure
H2NCHCOOH
CH2
C
CH
NH

Histidine
His

H2NCHCOOH
CH2
C
HN

CH
N
CH

Nomenclature of amino acid


Amino acids are named by considering them as amino
derivatives of carboxylic acids.
Example:

NH2
H

2
3

COOH

CH3

NH2
H

2
3

COOH

CH2OH

2-aminopropanoic acid

2-amino-3-hydroxypropanoic acid

(alanine, Ala)

(serine, Ser)

Exercise
Name the structure according to IUPAC nomenclature

NH2CHCOOH
CH2

NH2CHCH2CH2COOH
COOH

NH2 (CH2)4 CHCOOH


NH2

Zwitterion
A molecule with an overall charge of zero which has
positive charge on one atom and a negative charge on
another atom in the same molecule.

Example:

H3N

C
H

COO

zwitterion

Zwitterion
Amino acids can undergo an internal acid-base reaction,
in which a proton is transferred from the carboxyl (COOH) to the amino group (-NH2) to form dipolar ion
called zwitterion.

CH2CH2CH3

CH2CH2CH3
H

COOH

NH2
(neutral)

C
+

COO-

NH3

(dipolar ion @ zwitterion)

Isoelectric point (pI)


In general, zwitterion is electrically neutral and
exists at specific pH
This particular pH is called isoelectric points.
The pH at which an amino acid exists primarily
in its neutral zwitterion form and the
concentration of an amino acid is at maximum
Each amino acid has its specific pI
Example:
Amino Acid
Glycine
(Gly)

pI

Structure
H

CH
NH2

COOH

6.1

Isoelectric point

The cation, H3N+ CH2 COOH


predominates (Amino acids as base)
The anion, H2N CH2 COOpredominates (Amino acids as acid)
The zwitterion, H3N+CH2COOpredominates (Amino acids as
amphoteric)
NH2CH2COOH

Gly (pI = 6.1)

NH3CH2COOH

at pH < 6.1

NH3CH2COO-

NH2CH2COO-

at pH = 6.1

at pH > 6.1

Exercise
Serine, with an isoelectric point of 5.7 has the following
structure:
OH
O

H2N

OH

Draw the structures of serine at pH 3, pH 10 and its


isoelectric point.

19.2 Chemical Properties of Amino Acids


Learning Outcomes:
(a)Explain the reactions of amino acid with:
i. HCl
ii. NaOH
iii. NaNO2 + HCl
iv. Alcohol in the presence of an acid
catalyst.
(b)Describe the formation of peptide bond in
dipeptide.

a) Reaction with HCl

R'
C NH

2 +

HCl

R'
_
+
C N H 3C l
CO O H

CO O H
Example:

C H 2C H
H

NH

CO O H

C H 2C H

3
2 +

HCl

N H 3C l

CO O H

b) With Nitrous Acid (HNO2)

e lim in a tio n o f N 2 (g )

Observation:
Bubbling of gas (N2)

H 2O

R'
R

C +

CO O H
c a r b o c a t io n

2 -h y d ro x y
c a r b o x y lic a c id

Cl

h a lo c a r b o x y lic
a c id

- H

+
A lk e n o ic
a c id

Example:

CH3

H C NH2

NaNO2 / HCl

COOH

CH3
H C

COOH
diazonium ion
elimination of N2(g)
CH3
H C+
COOH
carbocation

H 2O
CH3
H C OH
COOH

+ Cl

-H

CH3
H C

Cl

COOH

CH2
H C
COOH

c) Reaction with NaOH

R'
C N H

2 +

N aO H

R'
C NH
_

C O O N a+

CO O H
Example:

C H 2C H
H

NH

CO O H

C H 2C H

3
2 +

N aO H

NH
_

3
2

C O O N a+

d) Reaction with ROH + HCl (catalyst)

R'
R C

R'
NH2 + R"OH

HCl

R C

NH3+Cl- + H 2 O

COOR"

COOH
Example:

C H 2C H
H

NH

CO O H

3
2 +

C H 3O H

HCl

CH2CH3
H C

NH3+Cl- + H 2 O

COOCH3

Peptide bond
Peptide Bond
2 amino acids react together, H2O is
eliminated.
This is condensation reaction.
Peptides are amino acid polymers in
which the individual amino acid units,
are linked together by amide bonds,
or peptide bonds
2 amino acids form dipeptide
3 amino acids form tripeptide
15 30 amino acids form oligopeptide
> 30 amino acids form polypeptide

Peptide bond
Formation of dipeptide :
O

H
H2N CH2 C OH + H N C COOH
H CH3
O
H2N CH2 C

H
N C COOH + H O
2
H CH3

amide bond /
peptide bond

A dipeptide

Notes:
N-terminal (with free NH2) is
always written on the left and
C-terminal (with free
COOH) at the right side

Formation of dipeptide :
COOH
HOCH2

COOH

NH2

CH3

NH2

Ala

Ser

Write the structural formula of dipeptide with the following


sequence Ser-Ala:

H O
H2N

H
NH C

CH2OH

COOH

CH3

A dipeptide

Exercise
Question 1
Phenylalanine (2-amino-3-phenylpropanoic acid) is an amino acid
which can exist in zwitterions form. Define zwitterions. Draw the
structure of phenylalanine and its zwitterions. Two molecules of
phenylalanine react to form a dipeptide. Draw the structure of the
dipeptide formed. Is the dipeptide optically active? Explain.
(6 marks)
.

Question 2
Serine and alanine are examples of -amino acid
COOH
CH3

NH2

COOH
HOCH2

Ala

Ser

NH2

Give the IUPAC name of serine. Draw the structures of serine each in
a strongly acidic and basic medium. Draw the structures of all
possible dipeptides when serine is reacted with alanine.
[5 marks]

Answer : Question 2
COOH
CH3

NH2

COOH
HOCH2

Ala

Ser

NH2

The structure of serine in a strongly acidic


and basic medium

All possible dipeptides when serine


is reacted with alanine