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• The term carbohydrate is derived from the french: hydrate de

carbone
• Most abundant organic compounds in nature (cellulose: 100 billion
tons annually) Also called saccharides, which means “sugars”
• A major source of energy from our diet

• Compounds composed of C, H, and O

• (CH2O)n when n = 5 then C5H10O5

• not all carbohydrates have this empirical formula: deoxysugars,

aminosugars
• Produced by photosynthesis in plants
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• Most carbohydrates are found naturally in bound form rather than
as simple sugars

• Polysaccharides (starch, cellulose, inulin, gums)

• Glycoproteins and proteoglycans (hormones, blood group
substances, antibodies)
• Glycolipids (cerebrosides, gangliosides)
• Glycosides
• Mucopolysaccharides (hyaluronic acid)
• Nucleic acids

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• sources of energy
• intermediates in the biosynthesis of other basic biochemical
entities (fats and proteins)
• associated with other entities such as glycosides, vitamins and
antibiotics)
• form structural tissues in plants and in microorganisms
(cellulose, lignin, murein)
• participate in biological transport, cell-cell recognition, activation
of growth factors, modulation of the immune system

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• Monosaccharides (monoses or glycoses)
 the simplest carbohydrates
 Empirical formula = CH2O
• Trioses, tetroses, pentoses, hexoses

• Oligosaccharides
• Di, tri, tetra, penta, up to 9 or 10
• Most important are the disaccharides

• Polysaccharides or glycans
• Homopolysaccharides
• Heteropolysaccharides
• Complex carbohydrates

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• also known as simple sugars

• classified by 1. the number of carbons and 2. whether aldoses or

ketoses
• most (99%) are straight chain compounds

• D-glyceraldehyde is the simplest of the aldoses (aldotriose)

• all other sugars have the ending ose (glucose, galactose, ribose,
lactose, etc…)

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• Monosaccharides are also classified according to the number
of carbon atoms
• A triose has three carbons; a tetrose has four carbons; a
pentose has five carbons; and a hexose has six carbons.

CH2OH
O
CHO
CHO HO H
HO H
HO H H OH H OH

CH2OH CH2OH H OH
CH2OH
OH
triose tetrose hexose
aldotriose aldotetrose ketohexose
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  Monosaccharides
Two- and three-carbon carbohydrates
H C O CH2OH
H C O H C O C O
CH2OH CH2OH CH2OH
Glycol aldehyde Glyceraldehyde Dihydroxyacetone
(aldehyde) (ketone)

1 H C O H C O CH2OH H C O
2 H C OH HO C H C O H C OH
3 HO C H H C OH HO C H HO C H
4 H C OH HO C H H C OH HO C H
5 H OH HO H H OH H C OH
6 CH2OH CH2OH CH2OH CH2OH
D-Glucose L-Glucose D-Fructose D-Galactose
(Aldose) (Aldose) (Ketose) (Aldose)

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Typical six-carbon carbohydrates
 Aldose sugars
H H H H H

C O C O C O C O C O

(H C OH)n H C OH H C OH H C OH H C OH

CH2OH CH2OH H C OH H C OH H C OH

Aldose Aldotriose CH2OH H C OH H C OH

n=1
Aldotetrose CH2OH
n=2 H C OH
Aldopentose
CH2OH
n=3
Aldohexose
n=4

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 Ketose sugars

CH2OH CH2OH
CH2OH
CH2OH
C O C O CH2OH
C O
C O
(H C OH)n H C OH C O
H C OH
CH2OH
CH2OH H C OH H C OH
CH2OH
CH2OH H OH
Ketose Ketotriose Ketotetrose
n=1 Ketopentose H C OH
n=0
n=2
CH2OH
Ketohexose
n=3

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 Monosaccharides
CH2OH
H O H
H α-D-Glucose
6C OH H
H
C O OH OH α-D-Glucopyranose
O
5
H C H C H 4 1 H OH
H
C C
3 2 H O CH2OH
H H
H α-D-Fructose
Pyran Pyranose H HO
structure OH OH α-D-Fructopyranose
OH H

O H2COH O CH2OH
6C C1
O
H C C H H HO α-D-Fructose
5 2
C C H OH α-D-Fructofuranose
H H 4 3 OH H
Furan Furanose
structure 14
Structure of a simple aldose and a simple ketose

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• Isomerism is the phenomenon whereby certain compounds, with the
same molecular formula, exist in different forms owing to their different organizations
of atoms.
•Isomers are molecules that have the same molecular formula, but have a
different arrangement of the atoms in space
• Structural Isomers are compounds that have the same molecular formula,
but the atoms are joined together in a different order.
•It arises owing to:
• Arrangement of Carbon skeleton
• Position of Functional group
• Different Functional groups

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• Arrangement of Carbon skeleton
e.g. The formula C4H10 represents two possible structural formulae, butane and
methylpropane:

• Position of Functional group

e.g. propan-1-ol and propan-2-ol

• different Functional groups

e.g. the molecular formula C2H60 represents both ethanol and methoxymethane.

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• Geometric isomers have atoms joined in the same order, but differ in
the orientation of groups around a double bond.
• e.g. cis-but-2-ene and trans-but-2-ene

• In the trans configuration, the methyl groups are on opposite sides of the
double bond.
• In the cis configuration, the methyl groups are on the same side of the
double bond.

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•Optical isomerism
•Involves an atom, usually carbon, bonded to four different atoms or groups of
atoms. They exist in pairs, in which one isomer is the mirror image of the other.

•These isomers are referred to as enantiomers.

•Enantiomers have identical physical constants, such as melting points and

boiling points, but are said to be optically active since they can be
distinguished from each other by their ability to rotate the plane of polarised
light in opposite directions.

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 H H
H H C O C O
C O C O HO C H HO C H
H C OH OH C H HO C H HO C H
H C OH OH C H H C OH HO C H
CH2OH CH2OH
H C OH H C OH
these two aldotetroses are enantiomers.
They are stereoisomers that are mirror CH2OH CH2OH
images of each other
these two aldohexoses are C-4 epimers.
they differ only in the position of the
hydroxyl group on one asymmetric carbo
(carbon 4)

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• Used to represent carbohydrates (chiral carbons)
• Places the most oxidized group at the top
• Uses horizontal lines for bonds that come forward
• Uses vertical lines for bonds that go back
• By convention, the letter L is assigned to the structure with
the —OH on the left
• The letter D is assigned to the structure with
—OH on the right
• The —OH on the chiral atom farthest from the carbonyl
group is used to assign the D or L configuration

D
D L

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• Most common hexose
• Found in fruits, corn syrup,
and honey
• An aldohexose with the
formula C6H12O6
• Known as blood sugar in the
body
• Building block for many
disaccharides and
polysaccharides
• Ketohexose C6H12O6
• Differ from glucose at C1 and C2 (location
of carbonyl)
CH2OH
• The sweetest carbohydrate (2x sucrose)
C O
• Found in fruit juices and honey
HO C H
• Formed from hydrolysis of sucrose
H C OH
• Converts to glucose in the body
H C OH
CH2OH

D-Fructose 30
• Aldohexose
• Differ from D-glucose at C4 CHO
• Not found in the free form in H C OH
nature HO C H
HO C H
• Obtained from lactose, a
H C OH
disaccharide (milk products)
CH2OH
• Important in cellular membranes
in CNS D-Galactose
• Anomers are isomers which differ in placement of hydroxyl on
C1
• The –OH is drawn down for the -anomer, and up for the -
anomer
CH2OH CH2OH
O 
O
OH
OH OH
OH OH OH
OH
 OH
-D-Glucose -D-Glucose
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• As a ketohexose, fructose forms a cyclic structure
when the —OH on C5 reacts with the ketone on C2
• Result is 5-atom ring
• Anomeric carbon is C2

CH2OH
C O CH2OH CH2OH CH2OH OH
O O
HO C H OH OH
H C OH OH CH2OH
H C OH OH OH

CH2OH
D-Fructose
-D-Fructose -D-Fructose 33
• A linear or branched carbohydrate usually from two to six monosaccharide units joined
by means of glycosidic bonds.

• Most common are the disaccharides

• Sucrose, lactose, and maltose
• Maltose hydrolyzes to 2 molecules of D-glucose
• Lactose hydrolyzes to a molecule of glucose and a molecule of galactose
• Sucrose hydrolyzes to a moledule of glucose and a molecule of fructose
• Glycosidic bond - The bond between the anomeric carbon of a carbohydrate and
some other group or molecule; the C-O in disaccharides and the C-N in nucleosides
are two examples.
• The glycosidic bond involves only the anomeric carbon.

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 CH 2OH CH 2OH
-D-Maltose
H O H H O H
H
O--D-Glucopyranosyl-(14)-
H
OH H
1 4
OH H -D-glucopyranose
OH O OH (glucose+glucose)
H OH H OH Reducing
group Reducing
CH 2OH CH 2OH group
-D-Lactose OH O H O OH
O--D-Galactopyranosyl-(14)- H H
OH
1  O 4
OH 
-D-glucopyranose H H
(glucose+galactose) H H H
H OH H OH
CH2OH
H CH2OH
O H H Sucrose
H O
1   2
H HO O--D-Glucopyranosyl-(12)-
OH H
OH O CH2OH -D-fructofuranose
H OH
(glucose+fructose)
OH H 35
36
 CH2 OH
O CH2 OH
1 O
OH
OH OH OH 1
OH OH
OH
alpha-D-Glucose
O alpha,beta-1,2-glycosidic bond
+
CH2 OHO OH CH2 OH O
OH 2 OH 2
CH2 OH CH2 OH
OH OH
beta-D-Fructose Sucrose 37
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 Hydrolysis of Sucrose
• Sucrose is hydrolyzed by the enzyme sucrase, which is secreted in the small
intestine
• The glucose and fructose can then be absorbed into the bloodstream
(disaccharides are too large to be absorbed)

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Maltose is
• A disaccharide also known as malt sugar.
• Maltose results from hydrolysis of starch by the enzyme
diastase
• Composed of two D-glucose molecules.
• Linked by an -1,4-glycosidic bond formed from the
 −OH on C1 of the first glucose and −OH on C4 of the
second glucose.
• Used in cereals, candies, and brewing.
• Found in both the - and β - forms.

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Lactose
• Is a disaccharide of β-D-
galactose and α- or β-D-
glucose.
• Contains a β -1,4-
glycosidic bond.
• Is found in milk and milk
products.
α-form

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In nature, carbohydrates are most often found as high molecular weight
polymers of monosaccharides.
These polysaccharides (sometimes called glycans) can be
homopolysaccharides (if all of the repeating units are the same), or
heteropolysaccharides (if the repeating units are not the same).
• Polysaccharides serve structural
purposes (cellulose and chitin), or serve
as fuel reserves (glycogen and starch).
• Polysaccharides do not have a defined
molecular weight. Remember that this is
in contrast to proteins. Any given protein
will always have the same molecular
weight and amino acid composition. This
because they are synthesized on a
template. This is not the case for
polysaccharides.
Starch is used by plants to store energy. It is found in all plant
seeds and tubers and is the principal form of glucose storage.
Starch can be separated into two principal polysaccharides,
amylose and amylopectin. Most plants (although exact numbers
vary) contain about 25% amylose and 75% quarters amylopectin.

Amylose is
• A polymer of α-D-glucose molecules.
• Linked by -1,4 glycosidic bonds.
• A continuous (unbranched) chain.
Amylopectin
• Is a polymer of α-D-
glucose molecules.
• Is a branched-chain
polysaccharide.
• Has α-1,4-glycosidic
bonds between the
glucose units.
• Has α-1,6 bonds to
branches.»

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Cellulose
• Is a polysaccharide of glucose
units in unbranched chains.
• Has β-1,4-glycosidic bonds.
• Cannot be digested by
humans because humans
cannot break down β-1,4-
glycosidic bonds.
• It constitutes over half of the
cell wall material of wood.
• Cotton is almost pure
cellulose.

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