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1
Amino Acids and Proteins
N Goalby
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Amino Acids
amine
group
carboxylic
acid group
R group can be a variety
of different things
depending on what amino
acid it is.
NH
2
CH CO
2
H
R
NH
2
CH
2
CO
2
H
The simplest amino acid is glycine, where the R is an H
key
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Chirality
CO
2
-
C
H
R
H
3
N
+
All amino acids, except
glycine, are chiral because
there are four different
groups around the C
chiral
centre
They rotate plane polarised light.
key
N H
2
C
CO
2
H
CH
3
H
NH
2
C
HO
2
C
CH
3
H
Some amino acids
You do not need to know any common names for the 20
essential amino acids. We should, however, be able to
name given amino acids using IUPAC organic naming
2-aminobutandioic acid
NH
2
CH
2
CO
2
H
(2-)aminoethanoic acid
NH
2
C CO
2
H
CH
2
H
OH
2-amino-3-hydroxypropanoic acid
H
2
N
C
CO
2
H
(CH
2
)
4
H NH
2
Lysine (basic)
2,6-diaminohexanoic acid
NH
2
C CO
2
H
CH
2
H
CO
2
H
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Some amino acids have an
extra carboxylic acid or an
amine group on the R group.
These are classed as acidic or
basic (respectively) amino
acids
NH
2
C CO
2
H
CH
2
H
CO
2
H
Aspartic acid
H
2
N
C
CO
2
H
(CH
2
)
4
H NH
2
Lysine (basic)
2,6-diaminohexanoic acid
Zwitterions
The no charge form of an amino acid never occurs. The
amino acid exists as a dipolar zwitterion.
The ionic interaction between zwitterions explains the
relatively high melting points of amino acids as opposed
to the weaker hydrogen bonding that would occur in the
no charge form
C N H
2
CO
2
H
H
R
C N H
3
+
CO
2
-
H
R
Zwitterion
Amino acids are often solids
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Reaction of amino acids
1 acidity and basicity
The amine group is basic and the carboxylic acid group is acidic.
Amino acids act as weak buffers and will only gradually change pH if small
amounts of acid or alkali are added to the amino acids.
COOH
C
H
2
N H
R
key
C N H
3
+
CO
2
-
H
R
C N H
2
CO
2
-
H
R
C N H
3
+
CO
2
H
H
R
OH
-
H
+ OH
-
H
+
Species in alkaline
solution
Species in
neutral solution
Species in acidic
solution
Acid base reactions of amino acids
NH
2
-CH
2
-CO
2
H + HCl Cl
-
NH
3
+
-CH
2
-CO
2
H
NH
2
-CH
2
-CO
2
H + NaOH NH
2
-CH
2
-CO
2
-
Na
+
+H
2
O
key
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Proteins
Proteins are polymers made from combinations of amino
acids.
The amino acids are linked by peptide links, which are
amide functional group.
NH CH C
R
O
NH CH C
R
O
NH CH C
R
O
key
The dipeptide phe-ala
C CH
O CH
2
N H
2
O H
C
O
CH
N
C H
3
OH H
H
+
C CH
O
CH
2
N H
2
C
O
CH N
C H
3
OH
H
Phenylalanine
alanine
Dipeptide 1
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The dipeptide phe-ala: second possibility
Phenylalanine
alanine
C
O
C H
NH
2
CH
3
O H
C
CH
O
CH
2
N
O H
H
H
C
CH
O
CH
2
N
O H
H
C
O
C
NH
2
CH
3
H
+
Dipeptide 2
Hydrolysis of di-peptides/proteins
If proteins are heated with dilute acid or alkali they can be
hydrolysed and split back in to their constituent amino
acids.
Breaks the peptide linkages in a protein molecule
Similar to digestion of proteins using enzymes
The composition of the protein molecule may be deduced by
using paper chromatography
key
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Hydrolysis of a Dipeptide
CH C
O
O
CH
3
N
H
H H
N CH C
O
O
CH
2
H
CH
C H
3
CH
3
H H
+ H
2
O
+ H
+
N CH C
O
O
CH
2
H
CH
C H
3
CH
3
H CH C
O
CH
3
N
H
H
key
Ninhydrin
If ninhydrin is sprayed on an amino acid and then heated for
10 minutes then red to blue spots appear.
This is done because amino acids are transparent and
cannot be seen.
Chromatography of amino acids
A mixture of amino acids can be separated by
chromatography and identified from the amount they have
moved.
R
f
value = distance moved by amino acid
distance moved by the solvent
Each amino acid has its own R
f
value
key
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Method chromatography
Take chromatography paper
and draw a pencil line 1.5cm
from bottom.
With a capillary tube put a
small drop of amino acid on
pencil line
Roll up paper and stand it in a
large beaker.
The solvent in the beaker
should be below the pencil line.
Allow to stand for 20 mins and
mark final solvent level
Spray paper with ninhydrin and
put in oven
distance
moved by
the
solvent
distance
moved by
the amino
acid
Solvent level
key
C
O
CH
3
O Na
+
Hydrolysis of amides
Amides can be hydrolysed by aqueous acids or alkalis.
With HCl an amide will be hydrolysed and split up in to the
original carboxylic acid and amine salt
With NaOH an amide will be hydrolysed and split up into the
amine and carboxylic acid salt.
If a compound contains an ester and amide group then both
functional groups can be hydrolysed by the action of acid
or alkali.
CH
3
CH
2
NH C
O
CH
3
+ NaOH CH
3
-CH
2
-NH
2
-
+
extra