Module 3.

1
DEMONSTRATING THE NATURE AND FUNCTION
OF BIOMOLECULES: CARBOHYDRATES

LO 3.1 Demonstrate the Nature and Function of

Biomolecules: Carbohydrates.
 Polyhydroxyketone or polyhydroxyaldehyde:

CO2 + H2O C6H12O6 + O2

CATEGORIES:
According to the number of saccharide:
•disaccharide – consisted of two monosaccharide units; can
be hydrolyzed into two simple sugars
•oligosaccharide – consisted of 3 – 10 saccharide units
•polysaccharide – consisted of more than 10 monosaccharide
According to the function of the carbonyl group:
•Aldoses – carbonyl group is an aldehyde
•Ketoses – carbonyl group is a ketone
•-monosaccharide – simple sugars; cannot be converted into
simpler sugars
According to the number of carbon atoms:
•Trioses – contain 3 carbon atoms
•Tetroses – contain 4 carbon atoms
•Pentoses – contain 5 carbon atoms
•Hexoses – contain 6 carbon atoms
D-ALDOSES
D-KETOSES
Koolman, J., & Röhm, K. H. (2005). Color atlas of biochemistry. Thieme Stuttgart.
 CARBOHYDRATE AS CELLULAR INFORMATION-
The ABO blood group antigens
Oligosaccharide components of glycolipids on surface of an
individual’s erythrocytes and other cells
ABO classifications of individuals is based on the oligosaccharide (a
chain of 3 to 10 monosaccharide units) assembly on the surface of
the red blood cells. These oligosaccharides act as antigens ( a foreign
substance that stimulate the production of antibodies (protein
molecules synthesize by the body to counteract foreign substances)

* A antigen is α-D-N-acetylgalactosamine

* B antigen is α-D-galactose

* A-type blood has A antigens on the surface of the red blood

cells and carries anti-B antibodies.

* B-type blood has B antigens on the surface of the red blood

cells and carries anti-A antibodies.

* AB-type blood has both A and B antigens on the surface of the

red blood cells and carries no anti-A and anti- B antibodies.

* O-type blood has neither A nor B antigens on the surface of the

red blood cells and carries both anti-A and anti- B antibodies.
 Physical Characters
• Condition:
Sugars are white, crystalline in shape and with sharp
melting points, while polysaccharides are white
amorphous solids.
• Taste:
Sugars have a sweet taste. Polysaccharides are
tasteless.
• Solubility:
Monosaccharides are soluble in cold water and hot
alcohol. Polysaccharides are partially soluble in hot
water.
• Optical activity:
• A compound is optically active when, in solution, it is capable to rotate the
plane of polarized light either to right (dextrorotatory, + or d) or to the left
(levorotatory, - or l).

• The optical activity of a compound is measured by determination of its

specific optical rotation ([] Dt) using a polarimeter, and applying the
following equation:
[]D25 =  /LC
Where:  = extension of rotation,
L = length of tube (light path) in decimeter,
C = concentration g /ml,
25 = operating temperature (t) in 0C,

D = line spectrum of sodium light (589 nm).

• Mutarotation
When a sugar is dissolved in water, the specific rotation of the
solution gradually changes until it reaches to a constant value
due to equilibrium between the a and b forms.
e.g. freshly prepared solution of b -glucose has a specific rotation
+112o. When this solution is allowed to stand the rotation falls till
reach + 52.7o.
The equilibrium reached is:
36% a –D- glucose [a]D = + 18.7 0
64% b –D- glucose [a]D = + 112 0
The sum is + 52.7o
 Chemical Reaction Related to Colour Tests for
Carbohydrates
• Effect of conc. acids:
Treatment with conc. mineral acid (HCl or H2SO4) leads to dehydration of sugars
and formation of the corresponding furfural.
• Reaction of furfural with amines resulted in Schiff’s bases with
different colours used as colour tests such as:
• Molisch’s test:
– Any carbohydrate + Alcoholic a-naphthol then add conc. H2SO4 on the wall
of the test tube Violet ring between the two layers.

• Resorcinol test (for keto-hexoses):

– Sugar solution + few crystals of Resorcinol + Equal volume of conc. HCl and
warm on water bath Rose Red Colour.

• Furfural test (Differentiate between Pentoses and Hexoses):

– Pentose + Coc. Acid and heat, expose the vapours to Aniline acetate paper
Red colour
– Hexoses give negative result.
 Effect of Alkalis
• Strong alkalis:
• Decomposition/Polymerization.
• Weak alkalis:
• Isomerization.
 Oxidation
• Mild Oxidation:
• These are oxidizing agents like Bromine water that convert the CHO group to COOH to
produce “onic acids”.
• Colour tests based on this reaction:
– Fehling’s reduction test:
Sugar solutions + Fehling’s A (CuSO4) + Fehling’s B (NaOH, NaK tartarate rochell salt),
heat on water bath Red Precipitate
RCHO + Cu++ RCOOH + Cu2O

CHO COOH
CH OH CH OH
I2 or Fehling's
HO CH HO CH
CH OH CH OH
CH OH CH OH
CH2OH CH2OH
D-Glucose Gluconic acid

- Barfoed’s test:
Sugar solution + Barfoed’s reagent (Cu Acetate/Acetic acid), heat for 3 minutes on boiling
water bath Red ppt with monosaccharides only.
Acidic medium decreases the oxidation power of Cu ++
 Strong Oxidation
• These are oxidizing agents like HNO3 that convert the CHO and
CH2OH group to COOH to produce “aric acids”.
CHO COOH
CH OH CH OH
HNO3
HO CH HO CH
CH OH CH OH
CH OH CH OH
CH2OH COOH
D-Glucose Saccharic acid
 • Galactaric acid (Mucic acid) test:
– Oxidation of galactose resulted in the formation of Galactaric
acid. It is a meso compound insoluble in water and have zero
optical rotation.

CHO COOH
CH OH CH OH
HNO3
HO CH HO CH
HO CH HO CH
CH OH CH OH
CH2OH COOH
D-Galactose Galactaric acid

A meso compound is a molecule with multiple stereocenters that is

superimposable on its mirror image. These particular traits lead to
specific qualities that meso compounds do not share with most other
stereoisomers. One such quality is the internal mirror plane.
 Enzymatic oxidation
• Takes place in plants and resulted in the oxidation of the primary
alcohol group only producing “uronic acids”.

CHO CHO COOH

CH OH CH OH O
H H OH
HO CH HO CH
CH OH CH OH
OHOH H H
CH OH CH OH
CH2OH COOH H OH
D-Glucose Glucuronic acid
 Reduction
• This resulted in the reduction of the CHO to CH2OH
producing “Sugar Alcohols”. Sodium borohydride or
H2/Pt are examples of reducing agents.
– Glucose Sorbitol
– Galactose Dulcitol
– Mannose Mannitol
CHO CH2OH
CH OH CH OH
HO CH HO CH
CH OH CH OH
CH OH CH OH
CH2OH CH2OH
D-Glucose Sorbitol