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19.1 : Introduction
Amino acid:
acid a compound that contains
both an amino group, -NH2 and a
carboxyl group, -COOH
H
CH3CH2
COOH
NH2
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
COOH
NH2
CH3
ii)
NH2
CH2OH
iii)
NH2
COOH
CH2CH2CH2NH2
iv)
COOH
NH2
v)
CH2CH2CH2COOH
COOH
NH2
12
COOH
NH2
(neutral)
CH2CH2CH3
H
COO-
NH3
(dipolar ion @
zwitterion)
13
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
NH3CH2COOH
at pH < 6.1
NH2CH2COO
at pH = 6.1
at pH > 6.1
16
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
19
NaOH
R'
R C NH2
_
COO Na+
COOH
Example:
CH2CH3
CH2CH3
H C NH2
COOH
NaOH
H C NH2
_
COO Na+
20
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
24
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
CH2
H2N CH2 C N C C
H CH3
OH
N C COOH
H
A tripeptide
25
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)
26
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
27