LEC 7: Carbohydrates A- Simple Sugars

A - Simple Sugars
Carbohydrates
– Contain the elements:
– are the most abundant class of organic
• Carbon
compounds found in living organisms.
• Hydrogen
– They originate as products of • Oxygen.
photosynthesis, an endothermic
reductive condensation of carbon – The name carbohydrate literally means
dioxide requiring light energy and the water compounds of carbon.
pigment chlorophyll.
– The general formula for simple sugars
is Cn(H2O)n.
GENERAL FORMULA:
– This class of compounds is better
n H2O + Energy → CnH2nOn + n O2
described as Polyhydroxy aldehydes
and Ketones.
– The formulas of many carbohydrates – The simplest carbohydrates are:
can be written as carbon hydrates,
Cn (H2O)n, hence their name.
• Glyceraldehyde
• Dihydroxyacetone.
– The carbohydrates are a major source
of metabolic energy, both for plants
and for animals that depend on plants
for food.

– Aside from the sugars and starches that

meet this vital nutritional role…

– carbohydrates also serve as a

A - Methods of Classification
structural material (cellulose),
Several methods are used to classify
carbohydrates.
Structural material (cellulose)

– a component of the energy transport

compound ATP, recognition sites on
cell surfaces, and one of three essential
components of DNA and RNA.
Carbohydrates are called saccharides or, if
they are relatively small sugars.
• Based on whether the carbohydrate
can be broken down into smaller units:
Monosaccharides
cannot be broken down into smaller units by
hydrolysis. Sometimes called simple sugars.
Disaccharides
can be broken down (hydrolyzed) into two
monosaccharide units.

Oligosaccharides
can be broken into three to six monosaccharide
units.

Polysaccharides
composed of 7 or more mono-saccharide units.
 • 2- If the OH group is found on the left side
of the chain of carbons, the sugar is
• Based on the number of carbon found in designated as an L sugar.
simple sugar:

3 carbons = Triose
4 carbons = Tetrose
5 carbons = Pentose
6 carbons = Hexose

C- Stereoconfigurations of simple sugars

• Another method uses the kind of carbonyl
group: H
CHO
C OH
CH2OH
D-glyceraldehyde
A- Aldose H
CHO
C OH
CHO
HO C H
A monosaccharide with an aldehyde H C OH H C OH
CH2OH
group. D-erythrose
CH2OH
D-threose
CHO CHO CHO CHO
HO C H H C OH HO C H H C OH
H C OH H C OH HO C H HO C H
H C OH H C OH H C OH H C OH
CH2OH CH2OH CH2OH CH2OH
D-arabinose D-ribose D-lyxose D-xylose

CHO CHO CHO CHO

CHO CHO CHO CHO
HO C H H C OH HO C H H C OH
HO C H H C OH HO C H H C OH
HO C H HO C H H C OH H C OH
HO C H HO C H H C OH H C OH
HO C H HO C H HO C H HO C H
H C OH H C OH H C OH H C OH
H C OH H C OH H C OH H C OH
H C OH H C OH H C OH H C OH
CH2OH CH2OH CH2OH CH2OH
CH2OH CH2OH CH2OH CH2OH

B- Ketose D-mannose D-glucose D-altrose D-allose D-tallose D-galactose D-idose D-gulose

A monosaccharide with a ketone group..

Usually combine the carbonyl classification and

the number classification together.

Cyclic Structures

Furanose rings
– Five membered sugar rings

B- Stereoconfigurations of simple
sugars.

Carbohydrates contain many stereocenters:

• If the OH group is found on the right side

of the carbon chain, the sugar is
designated as a D sugar.
 • Lactose
Pyranose rings
– Six membered sugar rings – Found in the polysaccharides:
• Starch
• Cellulose
• Glycogen

CHO
CH2OH
H C OH
H O
HO C H H
OH H H,OH
H C OH
H C OH OH
Carbohydrate Anomers H OH
CH2OH

– Formation of either of the cyclic form has

created a new stereocenter. Galactose

– These stereoisomeric ring forms of – Found in the disaccharide, lactose.

carbohydrates are called Anomers.
– Found in the cellular membranes of the
Anomers brain and nervous system.
– are carbohydrates that differ by the stereo- – Galactose is the C-4 epimer of glucose.
configuration of the carbon involved in ring
formation. CHO
CH2OH
H C OH
HO O
HO C H
The greek letters α and β are used to describe HO C H
H
OH H H,OH

the configuration about the ring forming carbon. H C OH

H
H OH
CH2OH
• The α anomer always has the OH group
oriented in a downward fashion on the Fructose
anomeric carbon of a D-sugar.
• The β anomer always has the OH group – Sweetest of the carbohydrates.
oriented in an upward fashion on the – Component of the disaccharide sucrose.
anomeric carbon of a D-sugar. – Fructose is a keto sugar.

Important Carbohydrates Disaccharides

composed of 2 monosaccharide units.

Monosaccharides Important disaccharides:

composed of three to seven carbon atoms.
• Maltose
Important monosaccharides: • Lactose
• Sucrose
• Glucose
• Galactose
• Fructose Maltose ( malt sugar )

– Used in cereals, candies and the brewing

Glucose of beverages.
– Composed of two D-glucose sugars joined
– The most abundant hexose in our diet. by an α-1,4 linkage.
– The building block of complex
carbohydrates.
CH2OH CH2OH
H O H H O OH
– Component of the disaccharides: H H
• Sucrose OH H OH H
OH O H
• Maltose
H OH H OH
 – Maltose is the disaccharide starting
material.
Lactose ( milk sugar )

– Found in milk and milk products.

– Composed of one galactose and one

glucose unit joined by a β-1,4 linkage.

CH2OH CH2OH
OH O H O OH
H H
O
OH H OH H
H H Glycogen
H OH H OH
– Animal starch. Storage form of glucose
found in the liver and muscle of animals.
Sucrose ( table sugar ) – Contains many highly branched glucose
units.
– Product of sugar cane and sugar beets.
– Joined by α-1,4 linkages and branched by
– Composed of one glucose and one
α-1,6 linkages.
fructose unit.
– Linkage is at both anomeric carbons.

CH2OH
H O H CH2OH H
O
H
OH H H OH
OH O
CH2OH
H OH OH H Dextrin
– Mixture of branched and un-branched
soluble polysaccharides produced by
Polysaccharides partial hydrolysis of starch by acids or
composed of many (more than 10) amylases.
monosaccharides.

Important polysaccharides: Reducing sugars

• Cellulose Any sugar that contains either:

• Starch • A free aldehyde group.
• Glycogen • An α-hydroxy ketone group.
• Dextrin
• • A hemiacetal linkage

Cellulose – The presence of any of these groups

allows the carbohydrate to undergo easy
– Major structural material of plant cells. oxidation.
– Consists of many glucose units joined by – If the sugar gets oxidized it causes
β-1,4 linkages. reduction.
– Thus the name “reducing sugar”
Starch
– Storage form of glucose found in rice
wheat, potatoes, grains, and cereals.
– Consists of many glucose units joined by
α-1,4 linkages.