Chapter 19:Amino Acids

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

CH3CH2

COOH

NH2

-amino acid: an amino acid in which

the amino group is on the carbon
adjacent to the carboxyl group
H

NH2

COOH

CH2CH3

Name
Glycine
Gly
Alanine
Ala
Valine
Val

Structure
H

CH

COOH

NH2
H3C

CH

COOH

NH2
CH3
HC

CH

COOH

CH3 NH2
3

Name
Leucine
Leu
Isoleucine
Ile
Phenylalanine
Phe

Structure
CH3
CHCH2

CH

CH3

NH2

CH3CH2CH
CH3

CH2

COOH

CH

COOH

NH2

CH

COOH

NH2

Name
Threonine
Thr
Cysteine
Cys
Methionine
Met

Structure
OH
CH3

CH2
CH2

HO

CH

NH2

CH2
NH

COOH

COOH
C
H

CH2 CH

COOH

NH2
5

Name

Structure

Tryptophan
Trp

O
OH
NH

Proline
Pro
Serine
Ser

CH2
CH2

HO

NH2

CH2
NH

COOH
C
H

CH2 CH

COOH

NH2
6

Name
Threonine
Thr

Structure
OH
CH3 C
H

Cysteine
Cys
Methionine

Met

HS

CH

COOH

NH2

CH2

CH

COOH

NH2

CH3 S CH2CH2

CH COOH
NH2
7

Name
Tyrosine
Tyr
Asparagine
Asn
Glutamine
Gln

Structure

HO

CH2

CH

COOH

NH2

NH2CCH2CH COOH

O
NH2

NH2CCH2CH2CHCOOH

O
NH2

Name

Structure

Aspartic
acid
Asp

HOOCCH2CHCOOH

NH2

Glutamic
acid
Glu

HOOCCH2CH2CHCOOH

NH2

Lysine
Lys

H2NCH2CH2CH2CH2CH COOH

NH2

Name
Arginine
Arg
Histidine
His

Structure
H2NCNH(CH2)3CHCOOH

NH
NH2

HCC=CH2CH COOH

N NH
NH2
CH

10

IUPAC Name

i)
H

COOH

2-amino ethanoic acid

COOH

2-amino propanoic acid

NH2
CH3

ii)

NH2
CH2OH

iii)

NH2

COOH

2-amino-3-hydroxy propanoic acid

11

CH2CH2CH2NH2

iv)

COOH

2,5-diamino pentanoic acid

NH2

v)

CH2CH2CH2COOH

COOH

2-amino hexanedioic acid

NH2

12

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
H

COOH

NH2

(neutral)

CH2CH2CH3
H

COO-

NH3

(dipolar ion @
zwitterion)

13

In general, zwitterion is electrically

neutral and exists at specific pH
This particular pH is called isoelectric points
Each amino acid has its specific pI
Example:
Amino Acid

Glycine
(Gly)

Structure
H

CH

COOH

pI
6.1

NH2

14

Lysine
(Lys)

Aspartic acid
(Asp)

9.7
H2N(CH2)4CH COOH

NH2

HOOCCH2CHCOOH

NH2

2.9

15

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)
Eg:
+

NH3CH2COOH

at pH < 6.1

NH2CH2COOH , Gly (pI = 6.1)

NH3CH2COO

NH2CH2COO

at pH = 6.1

at pH > 6.1

16

19.2 : Chemical Properties

i)Reactions of
NH2 group:
a) Reaction with HCl
R'
R C NH2

HCl

R'
_
+
R C NH3Cl
COOH

COOH
Example:

CH2CH3
H C NH2
COOH

CH2CH3
+

HCl

H C NH3Cl

COOH

17

i)Reactions of
NH2 group:
b) With Nitrous Acid (HNO2)
R'

R C NH2
COOH

NaNO2 / HCl
o

-5 to 0 C

R'

R C

COOH
diazonium ion
elimination of N2(g)

Observation: Bubbling
of gas (N2)

R'
R C+

H 2O
2-hydroxy
carboxylic acid

COOH
carbocation
+ Cl

halocarboxylic
acid

-H

+
Alkenoic
acid
18

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
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ii) Reactions of -COOH

group:
a) Reaction with NaOH
R'
R C NH2

NaOH

R'
R C NH2
_

COO Na+

COOH

Example:

CH2CH3

CH2CH3
H C NH2
COOH

NaOH

H C NH2
_

COO Na+

20

ii) Reactions of -COOH

group:
b) Reaction with ROH + HCl (catalyst)
R'
R C NH2

R'
R C NH2

R''OH

COOH

+ H 2O

COOR''

Example:

CH2CH3
H C NH2
COOH

CH3OH

HCl

R'
R C NH2

+ H 2O

COOR''

21

iii) 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

22

iii) Peptide
Bond
Formation of dipeptide bond
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
23

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

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iii) Peptide
Bond
Formation of tripeptide bond
O
H2N CH2 C OH

H
H N C COOH
H

Gly

CH2

OH

H N C COOH

CH3

H
Tyr

Ala

Write the structural formula of tripeptide with the following

sequence Gly-Ala-Tyr :
O

CH2

H2N CH2 C N C C
H CH3

OH

N C COOH
H

A tripeptide
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iv)
Importance
a) Importance of amino acids :
Human beings can synthesize about half
of the amino acids needed to make
proteins.
Other amino acids, called the essential
amino acids, must be provided in the
diet.
The ten essential amino acids are :
arginine (Arg) valine (val)
methionine (Met)
threonine (Thr) leucine (Leu) phenylalanine (Phe)
histidine (His) isoleucine (Ile) lysine (Lys)
trypthophan (Trp)

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iv)
Importance
b) Importance of proteins :
Proteins are the most abundant organic
molecules in animals, playing important
roles in all aspects of cell structure and
function.
Examples of protein functions :
Class of protein

Examples

structural protein

collagen, keratin

Functions
tendons, skin, hair, nails

enzymes

DNA polymerase

repair DNA

transport protein

hemoglobin

transport O2

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