Carbohydrate Chemistry

Biochemistry I
Lecture 2
Dr. Ahmed Maher

Fall 2020 1
Intended Learning Outcomes
By the end of the lecture students should be able to:

• Enumerate the functions of carbohydrates.

• Classify carbohydrates
• Classify monosaccharides according to number of
carbons and functional groups.
• Describe the ring structure of monosaccharide.
• Identify the reducing property of monosaccarides.
• State the derivatives and importance of
monosaccarides.
• Describe the composition of the disaccharides:
maltose, lactose and sucrose.
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Outline
• Function of Carbohydrates
• Classification of Carbohydrates
• Monosaccharides
• Disaccharides

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Definition
• Carbohydrates are polyhydroxy aldehydes or
polyhydroxy ketones or compounds that yield
these derivatives upon hydrolysis.
• They normally have the general formula of
Cn(H2O)n

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Functions of Carbohydrates

Source of
Energy

Intermediates
Storage of
of
Energy
metabolism

CHO
Structural
Fibers •Cell wall
•Cell Membrane

Nucleotides

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Classification of Carbohydrates
• Carbohydrates can be classified based on being
hydrolysable or not into:
– Monosaccharides: composed of 1 unit, carbohydrates
that cannot be hydrolyzed to simpler carbohydrates
(examples: glucose or fructose).
– Disaccharides: carbohydrates that can be hydrolyzed
into two monosaccharide units (example: sucrose,
which is hydrolyzed into glucose and fructose).
– Oligosaccharides: carbohydrates that can be
hydrolyzed into a few monosaccharide (3-10) units.
– Polysaccharides: carbohydrates that are polymeric
sugars (examples: starch or cellulose).
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Classification of Monosaccharides
• These are classified according to:
1. The number of carbons:
• Trioses (contain 3 carbons)
• Tetroses (contain 4 carbons)
• Pentoses (contain 5 carbons)
• Hexoses (contain 6 carbons)
• Heptoses (contain 7 carbons)
2. The functional group:
• Aldoses (contains an aldehyde)
• Ketoses (contains a ketone)
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Example of Aldoses

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Example of Ketoses

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Monosaccharides: Structure
• Monosaccharides can be represented in one
of two ways
– Open chain structure
– Ring / Cyclic / Howarth projection

Fall 2020 10
Monosaccharides: Structure
• Open Chain Structure

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Monosaccharides: Structure
• Cyclic Structure (Anomeric forms)
▪ Aldehydes and ketones can react with alcohols.
▪ Pentoses and hexoses can cyclize as the ketone or
aldehyde reacts with a distal OH.
▪ Glucose forms an intra-molecular hemiacetal, as the C1
aldehyde & C5 OH react, to form a 6-member pyranose
ring.
▪ Fructose forms a 5-member furanose ring, by reaction of
the C2 keto group with the OH on C5.

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Monosaccharides: Structure
• Cyclic Structure
In the cyclic structure the carbonyl group (anomeric carbon: C1
in aldoses and C2 in ketoses) becomes asymmetric and the sugar
will be present in 2 forms (anomers): α-form where OH is on the
right and β-form where OH is on the left.

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 Monosaccharides: Structure
• Cyclic Structure

Howarth Projection
The groups in the left are
written above the ring
while groups in the right
are written below the ring.

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α-D-Fructofuranose
Monosaccharides: Isomerism
• Derived from the aldotriose
glyceraldehyde.
• Carbohydrates differ in the
penultimate carbon (the
one before the last).
➢ Hydroxyl group in the left in
the L-form.
➢ Hydroxyl group in the right
in the D-form.
• Monosaccharides present
in nature are D-isomers

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Monosaccharides: Epimers
• Epimers are monosacchaides that differ from
each other with the respect to a single carbon
other than the anomeric carbon

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Glycoside Formation
• The anomeric hydroxyl and a hydroxyl of another sugar or some other
compound can join together, splitting out water to form a glycosidic bond:

R-OH + HO-R' → R-O-R' + H2O

• The glycosidic linkage is named after the anomeric carbon involved in its
formation (α or β-glycosidic linkage).
6 CH2OH 6 CH2OH

5 O 5 O
H H H H
H H
1 4 1
4 OH H OH H

OH O OH
3 2 3 2
α—1,4 glycosidic
H OH H OH
linkage
Fall 2020 17
Monosaccharides: Reducing Properties
• All monosaccarides have a reducing property due
to the presence of a free aldehyde or ketone
group.
• If the oxygen on the anomeric carbon (originally
the carbonyl group) of a sugar is not attached to
any other structure, the sugar is a reducing sugar.
• Reducing sugar can reduce cupric ions in
Benedict’s solution.

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Monosaccharides: Derivatives
1. Sugar Acids:
• Aldonic acids: obtained by oxidation of the aldehyde group
(example: gluconic acid).
• Uronic acids: obtained by oxidation of the primary alcohol
group (example: glucuronic acid).
• L-Ascorbic acid (Vitamin C): formed in plants and some
animals (not humans) from glucose.
2. Sugar Alcohols: formed by reduction of sugars (example: glycerol
and sorbitol).
3. Deoxysugars: 2-deoxyribose in DNA.
4. Amino Sugars: Formed by replacing the OH group at C2 by an
amino group (NH2) (examples: glucosamine and galactosamine).
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Monosaccharides: Importance
• Trioses: Glyceraldehyde-3-phosohate and dihyroxyacetone
phosphate are formed during glucose oxidation in living
cells.
• Pentoses: Ribose enters in RNA formation while
deoxyribose enters in DNA formation.
• Hexoses:
1. Glucose: main source of energy in our body.
2. Fructose (fruit sugar): forms the disaccharide sucrose
together with glucose.
3. Galactose: forms the disaccharide lactose together
with glucose.
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Disaccharides
• They are glycosides formed by the
condensation of 2 monosaccharides.
• If the glycosidic linkage involves the carbonyl
groups of both sugars, the resulting
disaccaride is non-reducing.
• If the glycosidic linkage involves the carbonyl
groups of one sugar, the resulting disaccharide
is reducing.

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Disaccharides: Maltose
• Maltose (Malt sugar) is formed by the action of amylase
enzyme on starch.
• It is formed of 2 molecules of α-D-glucopyranose linked by α-
1,4 glycosidic linkage.
• It is a reducing disaccharide.
• It is hydrolyzed by maltase enzyme to 2 molecules of α-D-
glucose. 6 CH OH 6 CH OH
2 2
5 O 5 O
H H H H
H H
1 4 1
4 OH H OH H

OH O OH
3 2 3 2
Maltose H OH
H OH Fall 2020 22
Disaccharides: Lactose
• Lactose (milk sugar) is formed of 1 molecule of β-D-
galactopyranose and 1 molecule of β-D-glucopyranose linked
by β-1,4 glycosidic linkage.
• It is a reducing disaccharide.
• It is hydrolyzed by lactase enzyme to galactose and glucose.

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Lactose
Disaccharides: Sucrose
• Sucrose (table sugar) is formed of 1 molecule of α-D-
glucopyranose and 1 molecule of β-D-fructofuranose linked by
α-1-β-2 glycosidic linkage.
• It is a non-reducing disaccaride.
• It is hydrolyzed by sucrase enzyme to fructose and glucose.

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Draw the following
• 2 Glucose molecules linked by β1,4
• Sucrose molecule

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Disaccharides: Sucrose

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Week 2 Students
• Prepare your own slides to explain lipid
classification in 15 mins.

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Thank You

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