SIJ1003

BIOCHEMISTRY OF CELL

LECTURE 1:
CARBOHYDRATE
 One of the 3 macromolecules/ macronutrient

Represent the most important source of energy

CARBO – HYDRATES
(C) (H2O)
 Classification of Carbohydrates
1. Monosaccharides

2. Disaccharides

3. Polysaccharides
 Monosaccharides
• Simplest compound, monomeric sugars.

• Empirical formula= (CH2O)n

• Smallest molecules of monosaccharides are called

trioses (3 carbon molecule).

• Trioses can be divided into glyceraldehyde and

dihydroxyacetone.

• Glyceraldehydes = aldehyde = aldose

• Dihydroxyacetone = ketone = ketose

• Same atomic composition.
• Different in the location of hydrogen and double bonds.
• This is also known as tautomers.
 Number of Aldose Ketose
carbon atoms
3 aldotriose ketotriose
4 aldotetrose ketotetrose
5 aldotpentose ketopentose

6 aldohexose ketohexose
How do we illustrate a monosaccharide?
• Chiral centers– carbon atom attached to 4 different
groups.

• The Fischer formula.

• Haworth formula (pyran, furan rings).
Fischer & Haworth formula
 Stereoisomers
• Isomers:
- Compounds with identical molecular formulas.
- Isomers can be categorized into constitutional isomers or
stereoisomers.

• Stereoisomers:
- Stereoisomers are isomeric molecules that have similar
molecular formula and constitution but differ in spatial
orientation.
- Stereoisomers can be divided into enantiomers and
diastereomers, epimers and anomers.
 Enantiomers
• Molecules that are mirror images of one another.
 Diastereomers
• Molecules where their chiral carbons are connected to
the exactly the same substrates at differing
configurations. Diastereomers are NOT mirror image.

D-glucose D-Altrose
 Epimers
• Epimers are two diastereomers that differ only at one
chiral centre/ carbon.

D-glucose D-mannose
 Anomers
• Molecules that differ in configuration at the
anomeric carbon.
• E.g:  and  configurations based on the position
of OH group at C1.
 Chapter 2 so far……
1. Monosaccaharides:
• Glyceraldehyde and dihydroxyacetone.
• Tautomers
• Examples of aldose sugars
• Fisher and Haworth projection
• Stereoisomers:
❑ Enantiomers
❑ Diastereomers
❑ Epimers
❑ Anomers
 Oligosaccharide-Disaccharides
• When an anomeric carbon of a carbohydrate reacts with
an OH group in a slightly acidic conditions, a glycosidic
bond is formed with the release of water.

Component
Disaccharide Description
monosaccharides
glucose 1α→2
sucrose common table sugar
fructose
product of starch glucose 1α→4
maltose
hydrolysis glucose
glucose 1α→1
trehalose found in fungi
glucose
galactose 1β→4
lactose main sugar in milk
glucose
galactose 1α→6
melibiose found in legumes
glucose
 Sucrose

• Most abundant disaccharide

• Major form of transport in plants
•
 Lactose

• Found in milk
• Normally, when we eat something containing lactose, an
enzyme in the small intestine called lactase breaks it down into
simpler sugar forms called glucose and galactose. These simple
sugars are then absorbed into the bloodstream and turned
into energy.
 Maltose

• Maltose is made up of two units of glucose,

In nature, used by germinating seeds for
energy.
• Slightly sweet, very soluble in water,
 Polysaccharide-complex sugar

1. Storage: Starch and glycogen.

2. Structural Material: Cellulose, hemicellulose, pectin,

chitin, dextran, inulin.

3. Connective tissue: Glycosaminoglycan – ex:

hyaluronic acid, chondroitin sulphate, heparin,
dermatan sulphate, keratan sulphate

4. Cell identification: Glycoprotein – proteoglycan.

5. Bacteria cell wall polysaccharides.

 Polysaccharide-complex sugar
1. Storage: Starch and glycogen.

2. Structural Material: Cellulose, chitin, dextran, inulin.

3. Connective tissue: Glycosaminoglycan – e.g:
hyaluronic acid, chondroitin sulphate, heparin,
dermatan sulphate, keratan sulphate

4. Cell identification: Glycoprotein – proteoglycan.

5. Bacteria cell wall polysaccharides.

 Glycogen & Starch
• There are stored in granules in cells.
• Starch is storage for plant and glycogen is storage
for animal cells.
• Main units starch is called amylose and
amylopectin.
• Amylose is a linear molecule (α 1-4) whereas
amylopectin and glycogen are branched polymers
(α 1-4 & α 1-6).
 Cellulose
• Major polysaccharide in woody and fibrous plants.
• Single most abundant single polymer in the biosphere.
• Very strong structure – very difficult to digest.
• Can be digested slowly by cellulase enzyme.
• Linear polymer of D-glucose.
• Linkages are β(1-4) glycoside.
• Bonded to hemicellulose, pectin & lignin in plant cell
walls.
• A lot of hydrogen bonding occur in the cellulose
microfibrils.
• Each microfibril consist of 50-100 cellulose molecules.
• Cellulose can exist as fully extended chains, with each
glucose residue flipped by 180° with respect to its
neighbour.
Cellulose structure
 Glycosaminoglycan
• Polysaccharide found in the intercellular spaces between cells in
tissues (extracellular) such as cartilage, tendon, skin, arterial wall
etc.
• Structural importance in vertebrate animals.
• Major functions in the formation of matrix to hold together proteins
components of skin and connective tissue.
• Made up of a long chain of repetitive disaccharide units, ex:
chondroitin sulphate;
• Each disaccharide unit is made up of an amino sugar and a
monosaccharide with a negatively charged (–ve) sulphate or
carboxylate group (sugar acid).
• Several types – hyaluronate, heparin, chondroitin 4 sulphate,
chondroitin 6 sulphate, dermatan sulphate, keratan sulphate.