Structure of Monosaccharides

Dr. Mohana Marimuthu

23rd January 2023
 Classification of carbohydrates
• Based on number of sugar units:

Monosachcarides Single sugar unit

Disaccharides Two sugar units
Trisachcarides Three sugar units
Oligosaccharides up to 9 sugar units
Polysaccharides > 10 sugar units

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 Monosaccharides, Continued
• Monosaccharides that contain an aldehyde group are
referred to as an aldose. Those that contain a ketone
group are referred to as a ketose.

• Monosaccharides are classified according to the

number of carbon atoms. Most common
monosaccharides have three to six carbon atoms.
– Triose contains three carbons.
– Tetrose contains four carbons.
– Pentose contains five carbons.
– Hexose contains six carbons.

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 Monosaccharides, Continued

• Carbohydrates are further classified on whether they

contain an aldehyde or ketone group.

• For example, glucose, the most abundant

monosaccharide found is nature, contains six carbons
and an aldehyde group. It is classified as an
aldohexose.

• Fructose, known as fruit sugar, contains six carbons

and a ketone group. It is classified as a ketohexose.

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 Monosaccharides, Continued

Aldohexose and ketopentose differ in the number of

carbon atoms and in the type of carbonyl group they
contain.

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 Monosaccharides, Continued

Stereochemistry in Monosaccharides

Multiple chiral centers

• Recall that a chiral center is a carbon atom that has
four different atoms or groups of atoms attached to
it.
• Glucose, a ketohexose, contains four different chiral
centers, each with a tetrahedral geometry.

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 Monosaccharides, Continued

Multiple chiral centers

• Carbons 2 through 5 of glucose
are tetrahedral and have four
different atoms or groups of
atoms attached. Carbons 1 and
6 are not chiral centers. Why?

C
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 Monosaccharides, Continued
Multiple chiral centers
• Groups bonded to each chiral center have two
different arrangements or mirror images, which
result in stereoisomers.
• The number of stereoisomers for a molecule
increases with the number of chiral centers in the
molecule.
• The general formula for determining the number of
stereoisomers is 2n, where n is the number of chiral
centers present in the molecule.
• Glucose has 4 chiral centers, so there are 16
stereoisomers, 24 = 16.
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 Monosaccharides, Continued

Representing stereoisomers—the Fischer projection

• Fischer projection is a simple way of indicating chiral
molecules by showing their three-dimensional
structure in two dimensions, without showing all the
wedges and dashes on all the chiral centers.
• In the Fischer projection, horizontal lines on a chiral
center represent wedges, and vertical lines on a
chiral center represent dashes.

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 Fischer Projections
• Used to represent carbohydrates (chiral carbons)
• Places the most oxidized group at the top (C1)
• Uses horizontal lines for bonds that come forward
• Uses vertical lines for bonds that go back
 D and L Notations
• 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
 D and L Monosaccharides
• Stereochemistry determined by the asymmetric center
farthest from the carbonyl group
• Most monosaccharides found in living organisms are D

D
D L
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 Monosaccharides, Continued

Representing stereoisomers—the Fischer

projection
• Enantiomers are written as if there is a mirror
placed between the two molecules.
• Enantiomers of D- and L-glucose are:

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 Monosaccharides, Continued

Stereoisomers that are not enantiomers

• How are all stereoisomers of D-glucose related since
only one mirror image exists for any stereoisomer?
• Stereoisomers that are not enantiomers are called
diastereomers.
• Diastereomers are stereoisomers that are not exact
mirror images.

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 Monosaccharides, Continued

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 Monosaccharides, Continued

• Galactose is found combined with glucose in the

disaccharide lactose, which is present in milk and
other dairy products.

• A single chiral center (carbon 4) in galactose is

arranged opposite that of glucose, which makes it a
diastereomer of glucose.

• Diastereomers that differ by one chiral center are

called epimers.

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 Monosaccharides, Continued

• Mannose, a monosaccharide, is found in some fruits

and vegetables.

• Cranberries contain high amounts of mannose, which

has been shown to be effective in urinary tract
infections.

• Mannose is an epimer of glucose.

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