CARBOHYDRATE

S
1: 2 :1
CLASSES OF CARBOHYDRATES
 Monosaccharides
 made up of 1 unit of sugar (simple sugar)

 Disaccharides
 made up of 2 units of monosaccharides

 Oligosaccharides
 made up of 2-10 monosaccharides units

 Polysaccharides
 made up of many units of sugar bonded together
 hydrolyze to many monosaccharide units.
 E.g., starch and cellulose have > 1000 glucose units.
 MONOSACCHARIDES
 Building blocks of all carbohydrates
 Common monosaccharides:
 Glucose
 Energy source for cells

 Fructose
 Sugar in fruits
C6H12O6
 Galactose
 Sugar in milk
 MONOSACCHARIDES
Classification of monosaccharides

Functional group No. of carbon atom

• Aldehyde : Aldose • 3 C : Triose

• Ketone : Ketose • 4 C : Tetrose

• 5 C : Pentose

• 6 C : Hexose
 No of Aldehyde Ketone
carbon (aldose) (ketose)
3C aldotriose ketotriose

4C aldotetrose ketotetrose

5C aldopentose ketopentose

6C aldohexose ketohexose

7C aldoheptose ketoheptose
ALDOSES
KETOSES
Exercise:
Classify the following monosaccharides according to their functional group
and number of carbon.

(a) (b) (c) (d)

 TYPE

• STEREOISOMERISM : Same molecular formula but different

structural formula.
• ENANTIOMER
• DIASTEREOMER
• EPIMER
ENANTIOMER
Enantiomer (optical isomer): Stereoisomers that are mirror
images to each other.
 Consist chiral carbon.

 TYPE

D AND L SUGAR
 Depends on the – OH position at 2nd last C.
 TYPE

EPIMER : Isomers differ at only 1 chiral center.

 TYPE

DIASTEREOMER : Isomers differ at more than 1 chiral center

but not mirror image.
HAWORTH PROJECTION
From linear (Fischer) carbohydrate to cyclic (Haworth) structure
Aldohexoses : hexagon
Ketohexoses : pentagon
EXERCISE
 Convert the following ketohexose into furan structure.
• Nomenclature
• Aldoses : pyran
• 2 structure ( α and β pyran)

• Ketoses : furan
• 2 structure ( α and β furan)
 CYCLIC - PYRAN

HAWORTH PROJECTION
EXERCISE
Convert the following monosaccharides into Haworth
projection. Identify and name the anomers.

D-galactose D-mannose
1. Convert the above monosaccharide to Fisher Projection.
2. Monosaccharide X is a C-3 epimer of the above monosaccharide. Draw
the structure of Monosaccharide X.
 CYCLIC - FURAN

HAWORTH PROJECTION

1. Shows the mechanism of the lone pair at –OH C-5 with C=O.

2. Put – O at the center (link btwn C-2 & C-5)

3. Lay down the Fisher projection.

right = down, left = up

4. Draw the furan structure. Fill in H and OH.

5. Produce anomers.
 CYCLIC - FURAN
HAWORTH PROJECTION

D-Fructose
 CYCLIC - FURAN
HAWORTH PROJECTION

b - D - Fructofuranose a - D - Fructofuranose
 DISACCHARIDES
1. Maltose = Glucose + Glucose
2. Lactose = Glucose + Galactose
3. Sucrose = Glucose + Fructose
LACTOSE
B-D-galactose + B-D-glucose
SUCROSE
a-D-glucose + B-D-fructose
SUCROSE
a-D-glucose + B-D-fructose
 CHEMICAL
REACTION
1. REDUCTION
- Aldehyde reduced to primary alcohol.
- Aldose produced Alditol.
 CHEMICAL
2. OXIDATION REACTION
a) by bromine water.
- aldehyde oxidized to carboxylic acid.
- Aldose produced Aldonic acid
 CHEMICAL
2. OXIDATION REACTION

b) by nitric acid
- Aldose produced Aldaric acid.

CHO CO2H
H OH H OH
HNO3 HO H
HO H
H OH H OH
H OH H OH
CH2OH CO2H
Glucaric acid