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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
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
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
pI
Structure
H
CH
NH2
COOH
6.1
Isoelectric point
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
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
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
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+
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
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