Introduction to Biochemistry

Lipid, Carbohydrates, Protein and amino Acids , Polymers

Chapter 4.0
Lipids
Chapter 4.2
 Lipids
Lipids are organic compound-found in living
organisms (exp: fats, oil, waxes, steroids)
Lipids are soluble in non-polar organic solvents
(exp: Diethyl ether, Chloroform, Carbon
tetrachloride, benzene)
Lipids have a variety of structure and function,
such as:

cortisone vitamin A tristearin

a hormone a vitamin a fat
Carbohydrate
Chapter 4.3
 Introduction
General formula Cn(H2O)n
All have C=O and –OH functional group
Classified based on
Size of carbon chain
No of sugar units
Location of C=O
 Monosaccharide
Simplest carbohydrate. Sweet and
commonly known as sugar
Classified according to number C atoms
a. 3C – triose
b. 4C – tetrose
c. 5C – pentose
d. 6C - heksose
with aldehyde group –aldose sugar
with ketone group –ketose sugar.
 O H
C
aldo- aldehyde group
H C OH
hex – 6 carbon
HO C H
ose - carbohydrate
H C OH
H C OH
CH2OH aldohexose
 CH2OH
C O keto- ketone group
HO C H hex – 6 carbon
H C OH
ose - carbohydrate
H C OH
CH2OH
ketohexose
 Structural isomers

O CH2OH

C H C O
H C OH H C OH
H C OH H C OH
HO CH2 HO CH2

aldotetrose ketopentose
No. of Carbon Aldose sugar Ketose sugar
3 aldotriose Ketoriose

4 aldotetrose Ketotetrose

5 aldopentose Ketopentose

6 aldohexose ketohexose
Protein and Amino Acids
Chapter 4.4
 Proteins
Amino acids are the basic structural units of proteins. An
amino acid is a compound that contains at least one amino
group (-NH2) and at least one carboxyl group (-COOH)

H O H O
+
H3N C C O- + +H3N C C O-
R1 R2

Peptide bond
H O H O
+
H3N C C N C C O- + H2O
R1 H R2

25.3
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
 Amino acid:
acid a compound that contains both an
amino group, -NH2 and a carboxyl group, -COOH
H
CH3CH2 C COOH
NH2

-amino acid: an amino acid in which the amino group

is on the carbon adjacent to the carboxyl group

H

NH2 C COOH
CH2CH3
 20 amino acids

Name Structure

Glycine
Gly

Alanine H3C CH COOH

Ala NH2

Valine CH3

Val HC CH COOH

CH3 NH2
Name Structure

Leucine CH3

Leu CHCH2 CH COOH

CH3 NH2

Isoleucine CH3CH2CH CH COOH

Ile CH3
NH2

Phenylalanine
Phe CH2 CH COOH
NH2
Name Structure
OH
Threonine
CH3 C CH COOH
Thr
H NH2
CH2 CH2 COOH
Cysteine
C
Cys CH2 NH H

Methionine HO CH2 CH COOH

Met NH2
Name Structure
O
Tryptophan
OH
Trp NH2
NH
CH2 CH2 COOH
Proline
C
Pro CH2 NH H

Serine HO CH2 CH COOH

Ser
NH2
Name Structure
Threonine OH

Thr CH3 C CH COOH

H NH2
Cysteine HS CH2 CH COOH
Cys NH2

Methionine CH3 S CH2CH2 CH COOH

Met NH2
Name Structure

Tyrosine
HO CH2 CH COOH
Tyr NH2

Asparagine NH2─C─CH2─CH ─COOH

║ │
Asn O NH2

Glutamine NH2─C─CH2CH2─CH─COOH
Gln ║
O
│
NH2
Name Structure
Aspartic HOOC─CH2─CH─COOH
acid │
NH2
Asp
Glutamic HOOC─CH2CH2─CH─COOH
acid │
NH2
Glu
Lysine H2N─CH2CH2CH2CH2─CH ─COOH
│
Lys NH2
Name Structure
Arginine H2N─C─NH─(CH2)3─CH─COOH
│ │
Arg NH NH2

Histidine HC─C=CH2─CH ─ COOH

His │ │ │
N NH NH2

CH
25.3
 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,
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)
 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 Functions

structural protein collagen, keratin tendons, skin .

hair, nails
enzymes DNA polymerase repair DNA

transport protein hemoglobin transport O2

Polymers
Chapter 4.0
A polymer is a high molar mass molecular compound made up
of many repeating chemical units.

Naturally occurring polymers

•Proteins
•Nucleic acids
•Cellulose
•Rubber
Synthetic polymers
•Nylon
•Dacron
•Lucite
25.1
 Introduction

Polymer
- is a macro molecule that is made up of many small repeating units
called monomers linked together by covalent bond.

nA -A-A-A-A-A-A-A-A-n

- monomer
polymer polymer
can be represented by their repeating unit in the long
chain.

nA -A-n
Monomer polymer
- is a basic molecular units that can joinedunit)
(repeating to many others to form
a polymer.
 Homopolymer
- a polymer formed from only one types monomer units.

nA -A-n

- Example :
nCH2 CH2 -CH2CH2-n

ethene polyethene
(ethylene) (polyethylene)
The simple repeating unit of a polymer is the monomer.

Homopolymer is a polymer made up of only one type of

monomer
( CF2 CF2 )n ( CH2 CH2 )n ( CH2 CH )n

Teflon Polyethylene Cl
PVC

25.2
 Copolymer
- a polymer formed from two or more different monomers.

nA + nB -A-B-n

- Example :

nCH2 CCl2 + nCH2 CHCl -CH2-CCl2-CH2-CHCl-

n
1,1-dichloroethene 1-chloroethene Saran®
Copolymer is a polymer made up of two or more monomers

( CH CH2 CH2 CH CH CH2 )n

Styrene-butadiene rubber

25.2
 21.2 : Structures of Polymers

21.2.1 : Linear Polymers

Linear polymer is a polymer consist of monomers that are
linked in straight and long continuous chain.
Linear or straight-chain polymer can be folded back upon
themselves in a random fashion.
Linear polymer is recycleable because it is soft and can be
reformed when heated.

-A-A-A-A-A-A-A-A-n
monomers link together
in a straight chain
folded linear polymer
in a random fashion
21.2.2 : Cross-linked Polymers

Cross-linked polymer contains branches that connect linear polymer chain, as shown
in the figures below.

-A-A-A-A-A-A-A-A-A-A-A-A-
X X
-A-A-A-A-A-A-A-A-A-A-A-A-
Cross-linked polymer is harder (rigid) and more elastic polymer compared to linear
polymer.
• Long polymer chain cross-linked by branched
It also cannot be remelted or remolded again.

The equation below shows the chemical reaction for the rubber vulcanization
process.
In a vulcanization process, long chain of polyisoprene are cross-linked by sulphur
atoms.

CH3 CH3
-CH2C CH-CH2- + -CH2C CH-CH2-

sulphur

CH3 CH3
-CHC CH-CH2-CHC CH-CH2-

After vulcanization S
rubber becomes moreSstable over wide ranges of temperature
and far more durable than natural rubber.
-CHC CH-CH2-CHC CH-CH2-
CH3 CH3
 21.3 : Types of Polymers

21.3.1 : Natural Polymers

Natural polymers are polymers that synthesized in nature
or naturally occurring polymers.

i. Proteins
Protein are the most abundant organic molecules in animals
such as enzymes, hormones, hemoglobin and many other
things.
It is a natural polymer built from amino acids linked by
amide bonds.

H O
HN-C-C
R n
ii. Carbohydrates
Carbohydrates such as starch is also a polymer.
i. Starch (amylose)

CH2OH CH2OH
O O
H H HH H H
O OH H O OH H O

H OH H OH
ii. Starch (amylopectin) n
- α-(1,4)-glycosidic
contains α-(1,4)-glycosidic linkages linkages.
and α-(1,6)-glycosidic
iii.Natural Rubber
Natural rubber is a polymer of 2-methyl-1,3-butadiena, also known as
isoprene.

n CH2=C-CH=CH2 -CH2-C=CHCH2-
CH3 CH3 n
Another name for natural rubber is cis-1,4-polyisoprene.
isoprene cis-polyisoprene
All the double bond in natural rubber are cis- configuration.
Natural rubber is soft, not strong or elastic and sticky, that makes it less
useful.
In order to make it more useful rubber has to undergo a vulcanization process.
21.3.2 : Synthetic Polymers

Synthetic polymers are polymers that are prepared in industries from

monomers that have gone through polymerization process.
Polymerization is a process that combines monomers to form polymers.
Synthetic polymers can be classified base on their method of
preparation ( polymerization process ).

21.3.2.1 : Addition Polymerization

Addition polymerization is the addition reaction in which unsaturated

monomers are joined together by covalent bonds to form a polymer
without elimination of a small molecule.
Polymers obtained by addition polymerization are called addition
polymers.
 Therefore, addition polymer always involves the
polymerization of monomers which have double bond within
the monomers.
Peroxide is used as initiator in addition polymerization.

i. Formation of polyethene

n CH2 CH2 ROOR -CH

( 2-CH2-
)n
ethene polyethene

ii. Formation of polyvinyl chloride

n HC CH2 ROOR (
-HC-CH 2-
)n
Cl Cl
chloroethene polychloroethene
(polyvinyl chloride or PVC)
iii.Formation of polystyrene

n HC CH2 ROOR (
-HC-CH 2-
)n

phenylethene Polyphenylethene
(styrene) (polystyrene)

iv. Formation of polyisopropene

n CH 2 =C-CH=CH 2 -CH 2 -C=CHCH 2 -

CH 3 CH 3 n

isoprene polyisoprene
21.3.2.2 : Condensation Polymerization

Condensation polymerization is a process that combines the monomers

with elimination of a small molecule such as water, methanol, hydrogen
chloride or ammonia to form a polymer.

The polymers obtained from condensation polymerization are called

condensation polymers.

The monomers involves in this polymerization must have at least two

identical or different functional group in the molecule.

When a carboxylic acid with two –COOH group reacts with an amine
with two –NH2 groups, a polyamide is formed.

When a carboxylic acid with two –COOH group reacts with an alcohol
with two –OH groups, a polyester is formed.
(A). Polyamides
i. Formation of Nylon 6,6
O O
n H2N-(CH2)6-NH2 + n HO-C-(CH2)4-C-OH
hexane-1,6-diamine hexane-1,6-dioic acid

H H O O
(
-N-(CH 2)6-N-C-(CH2)4-C-
)n + n H2O
Nylon 6,6
ii. Formation of Nylon 6

O O
n H2N-(CH2)5-C-OH (
-NH-(CH 2)5-C-
)n + n H2O
6-aminohexanoic Nylon 6
iii. Formation of Kevlar

H H O O
n H-N- -N-H + n Cl-C- -C-Cl

1,4-diaminobenzene terephthalic acid

H H O O
(B). Polyester
N- -N-C- -C n + n HCl
The repeating functional groups in this polymer chain are ester.
The most familiar polyester is polyethylene terephthalate known as Dacron and
Terylene. Kevlar
 The polymer is formed by the reaction of ethylene glycol
with methyl ester or tetephtalic acid.
In this process, a molecule of methanol is split out for
each new ester group formed.

i. Formation of Dacron

O O
n CH3O-C- -C-OCH3 + n HO-CH2CH2-OH
1,2-ethanediol
dimethyl terephthalate
(ethylene glycol)

O O
(
-O-CH 2CH2-O-C- -C-
)n + n CH3OH

Dacron or poly(ethylene terephthalate) metanol

ii. Formation of Terylene

O O
n HO-CH 2CH 2-OH + n HO-C- -C-OH
ethane-1,2-diol benzene-1,4-dicarboxylic acid

O O
(
-O-CH 2CH 2-O-C- -C-
)n + n H 2O
water
Terylene
 21.4 : Uses of Synthetic Polymers

No. Polymer Uses

1 Polyethene plastics, drinking bottles, toys
Polyvinyl piping, floor tiles, clothing, toys,
2
chloride wire covering
3 Polystyrene containers, thermal insulation-ice buckets
4 Nylon 6 Textile
5 Nylon 6,6 Sweater
6 Kevlar Bullet proof vest
7 Dacron Fabric
8 Terylene Fiber-optic material
25.2