Course code: BIO203
Course title: General Physiology
Content: The Chemistry of Carbohydrates
Lecturer: Dr M. O. Jimoh
Carbohydrates
- Carbohydrates are polyhydroxy aldehydes or ketones, or substances that yield such
compounds on hydrolysis.
- Carbohydrates have the empirical formula (CH2O)n.
- Carbohydrates are the most abundant biomolecules on earth.
- Oxidation of carbohydrates is the central energy-yielding pathway in most non-
photosynthetic cells.
General properties of carbohydrates
- Carbohydrates act as energy reserves, also stores fuels, and metabolic intermediates.
- Ribose and deoxyribose sugars forms the structural frame of the genetic
material, RNA and DNA.
- Polysaccharides like cellulose are the structural elements in the cell walls of bacteria
and plants.
- Carbohydrates are linked to proteins and lipids that play important roles in cell
interactions.
- Carbohydrates are organic compounds; they are aldehydes or ketones with many
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hydroxyl groups.
Physical Properties of Carbohydrates:
- Stereoisomerism- Compounds having the same structural formula but they differ in
spatial configuration. Example: Glucose has two isomers with respect to penultimate
carbon atom. They are D-glucose and L-glucose.
- Optical Activity- It is the rotation of plane polarized light forming (+) glucose and (-)
glucose.
- Diastereoisomerism- It is the configurational change with respect to C2, C3, or C4 in
glucose. Example: Mannose, galactose.
- Anomerism- It is the spatial configuration with respect to the first carbon atom in aldoses
and second carbon atom in ketoses.
Biological Importance of Carbohydrates
- Carbohydrates are chief energy source, in many animals, they are instant source of
energy. Glucose is broken down by glycolysis/ Kreb's cycle to yield ATP.
- Glucose is the source of storage energy. It is stored as glycogen in animals and starch in
plants.
- Stored carbohydrates act as energy source instead of proteins.
- Carbohydrates are intermediates in biosynthesis of fats and proteins.
- Carbohydrates aid in regulation of nerve tissue and as the energy source for brain.
- Carbohydrates get associated with lipids and proteins to form surface antigens, receptor
molecules, vitamins and antibiotics.
- They form structural and protective components, like in cell wall of plants and
microorganisms.
- In animals they are important constituent of connective tissues.
- They participate in biological transport, cell-cell communication and activation of
growth factors.
- Carbohydrates rich in fibre content help to prevent constipation.
- Also, they help in modulation of immune system.
Classes of carbohydrates
There are three major classes of carbohydrates:
i. Monosaccharides
- Monosaccharides, or simple sugars, consist of a single polyhydroxy aldehyde or
ketone unit.
- The most abundant monosaccharide in nature is the six-carbon sugar D- glucose,
sometimes referred to as dextrose.
- Other monosaccharides are fructose, galactose and xylose.
ii. Disaccharides
- Disaccharides are simple sugars.
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- They are formed when two monosaccharides joined together by glycosidic linkages
- They are soluble in water.
- Examples of disaccharides are sucrose, maltose and lactose
iii. Oligosaccharides
- An oligosaccharide is a saccharide polymer containing typically three to nine of
simple sugars.
- Oligosaccharides consist of short chains of monosaccharide units (3-9), or
residues, joined by characteristic linkages called glycosidic bonds.
- Oligosaccharides can have many functions, for example, they are commonly
found on the plasma membrane of animal cells where they can play a role in cell-
cell recognition.
- Common examples are raffinose, maltodextrins, stachyose.
iv. Polysaccharides
- The polysaccharides are sugar polymers containing 10 or more monosaccharide
units.
- Some have hundreds or thousands of monosaccharide units.
- Polysaccharides are of two types based on their function and composition.
- Based on functions, polysaccharides are of two types: storage and structural.
a. Storage polysaccharide – starch and glycogen
b. Structural polysaccharide – cellulose and chitin
Monosaccharides
- The word “Monosaccharides” derived from the Greek word “Mono” means Single and
“saccharide” means sugar.
- Monosaccharides are polyhydroxy aldehydes or ketones which cannot be further
hydrolysed to simple sugar.
- Monosaccharides are simple sugars.
- They are sweet in taste.
- They are soluble in water.
- They are crystalline in nature.
- They contain 3 to 10 carbon atoms, 2 or more hydroxyl (OH) groups and one aldehyde
(CHO) or one ketone (CO) group.
Classification of Monosaccharides
- Monosaccharides are classified in two ways.
i. Based on the number of carbon atoms present in them.
ii. Based on the presence of carbonyl group.
i. Based on the number of carbon atoms present in them
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- The naturally occurring monosaccharides contain three to seven carbon atoms
per molecule.
- Monosaccharides of specific sizes may be indicated by names composed of a stem
denoting the number of carbon atoms and the suffix -ose.
- For example, the terms triose, tetrose, pentose, and hexose signify
monosaccharides with, respectively, three, four, five, and six carbon atoms.
Trioses
- Trioses are monosaccharides containing 3 carbon atoms.
- The molecular formula of triose is C3H6O3
Characteristics of trioses
- Trioses are simple sugars.
- They are soluble in water.
- They are sweet in taste.
- The triose may contain an aldehyde group (aldotriose) or a ketone group (ketotriose).
- Examples are glyceraldehyde and dihydroxyacetone
Tetroses
- Tetroses are monosaccharides containing 4 carbon atoms.
- The molecular formula of a tetrose is C4H8O4
Characteristics:
- Tetroses are simple sugars.
- Tetroses are soluble in water.
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- They are sweet in taste.
- They are crystalline forms.
- The tetroses may contain an aldehyde group (aldotetrose) or a ketone group
(ketotetrose).
Pentoses
- Pentoses are monosaccharides containing 5 carbon atoms.
- It is an important component of nucleic acids (DNA & RNA).
- The molecular formula of Pentose is C5H10O5
Characteristics of pentoses
- Pentoses are simple sugars
- Pentoses are soluble in water
- They are sweet in taste.
- They are crystalline forms.
- The pentoses may contain aldehyde group (aldopentoses) or ketone group
(ketopentoses)
Pentose
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Hexoses
- Hexoses are monosaccharides containing 6 carbon atoms.
- The molecular formula of Hexose is C6H12O6
Characteristics:
- Hexoses are simple sugars
- Hexoses are soluble in water.
- They are sweet in taste.
- They are crystalline forms.
- The hexoses may contain an aldehyde group (aldohexose) or a ketone group
(ketohexose).
ii. Based on the presence of carbonyl group
- Monosaccharides are also classified as aldoses or ketoses.
- Those monosaccharides that contain an aldehyde functional group are called
aldoses.
- Those containing a ketone functional group on the second carbon atom are
ketoses.
- Combining these classification systems gives general names that indicate both the
type of carbonyl group and the number of carbon atoms in a molecule.
- Thus, monosaccharides are described as aldopentoses, aldohexoses, ketopentoses,
ketohexoses, and so forth.
- Glucose and fructose are specific examples of an aldohexose and a ketohexose,
respectively.
Structure of Monosaccharides
i. Straight or Open Chain Structure
- Here, the 6 carbon atoms of glucose are arranged in a straight line.
- It is also called open chain structure because the two ends remain separate, and
they are not linked.
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- Open chain structures are of two types:
a. Structure proposed by Fittig and Baeyer
b. Structure proposed by Fischer known as Fischer’s Projection Formula
ii. Cyclic or Ring Structure
- Here the atoms are arranged in the form of a ring.
- Haworth (1929) proposed this formula and hence the name Haworth’s Projection
Formula.
- The sugar molecules exist in two type of rings which are as follows
a. Furanose ring – 5 membered ring
b. Pyranose ring- 6 membered ring
Properties of Monosaccharides
- Colour – colourless
- Shape – crystalline
- Solubility – in Water
- Taste – sweet
- Optical activity – Optically active.
a. Dextrorotatory (‘D’ form) and
b. Levorotatory (‘L’ form)
- Mutarotation – The change in specific rotation of an optically active compound is
called mutarotation. +1120 +52.50 +190 α-D-glucose β -D-glucose
- Glucoside formation
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Glucose + Methyl alcohol = Methyl glucoside
- Esterification –
- Reducing agents –
- Monosaccharides reduce oxidizing agent such as hydrogen peroxide. In such
reaction, sugar is oxidized at the carbonyl group and oxidizing agent becomes
reduced.
- Formation of Osazone –
Disaccharides
- Disaccharides consist of two sugars joined by an O-glycosidic bond.
- The most abundant disaccharides are sucrose, lactose and maltose.
- Other disaccharides include isomaltose, cellobiose and trehalose.
Classifications of disaccharides
i. Homodisaccharides
ii. Heterodisaccharides
Homodisaccharides are formed from similar monosaccharide units
Homodisaccharides Maltose (malt sugar) Isomaltose Cellobiose
Structure 2α-glucose 2 α-glucose 2β-D-glucose
Type of bond α-1-4 glucosidic bond α1-6 glucosidic bond β1-4 glucosidic bond.
Anomeric Carbon Free Free Free
Reducing Property Reducing Reducing Reducing
Produced by It is produced from by the hydrolysis of By the acid hydrolysis
starch by the action of some of cellulose
amylase polysaccharides
such as dextran
Heterodisaccharides are formed of 2 different monosaccharide units
Heterodisaccharides Sucrose Lactose
Composition α-D-glucose+ β–D-fructose β-D-galactose and β-D-glucose
Type of bond α-1-β-2 glucosidic bond OR a β (1-4) galactosidic bond
β 2-α-1 fructosidic bond
Anomeric C no free aldehyde or ketone group Free
Reducing property is not a reducing sugar Reducing
Composition α-D-glucose+β–D-fructose β-D-galactose and β-D- glucose
Effect of hydrolysis The hydrolysis of sucrose to Hydrolysed by the intestinal
glucose and fructose is catalysed lactase enzyme into galactose and
by sucrase (also called invertase) glucose
Present in Table sugar Cane sugar, beet Milk sugar. It may appear in urine in
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sugar late pregnancy and during lactation
Polysaccharides
- Polysaccharides contain hundreds or thousands of carbohydrate units.
- Polysaccharides are not reducing sugars, since the anomeric carbons are
connected through glycosidic linkages.
Nomenclature:
- Homopolysaccharide- a polysaccharide is made up of one type of
monosaccharide unit
- Heteropolysaccharide- a polysaccharide is made up of more than one type of
monosaccharide unit
Starch
- Starch is a polymer consisting of D-glucose units.
- Starch is a storage polysaccharide in plants, and made of glucose units
- It is a homopolysaccharide made up of two components: amylose and amylopectin.
- Most starch is 10-30% amylose and 70-90% amylopectin.
- Amylose – a straight chain structure formed by 1,4 glycosidic bonds between α-D-
glucose molecules.
- Starches (and other glucose polymers) are usually insoluble in water because of
the high molecular weight, but they can form thick colloidal suspensions with
water.
6CH OH CH2OH
C H2OH 2 CH2OH CH2OH
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HH O HH
H H H H
H1 OH
OH H1 4 OH OH OH
OH
OH
3 2
OH H OH H OH OH H OH
amylose
Glycogen
- Glycogen is the storage polysaccharide in animals
- Glycogen constitutes up to 10% of liver mass and 1-2% of muscle mass
- Glycogen is stored energy for the organism.
- Similar in structure to amylopectin, only difference from starch: number of branches
- Alpha (1,6) branches every 8-12 residues.
- Like amylopectin, glycogen gives a red-violet color with iodine.
Cellulose
- In cellulose, the β-glucose molecules are joined by condensation, i.e. the removal of
water, forming β-(1,4) glycosidic linkages.
- The glucose units are linked into straight chains each 100-1000 units long.
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- Weak hydrogen bonds are formed between parallel chains binding them into cellulose
microfibrils.
- The cellulose fibres are often “glued” together by other compounds such as
hemicelluloses and calcium pectate to form complex structures such as plant cell walls.
- Because of the β-linkages, cellulose has a different overall shape from amylose,
forming extended straight chains which hydrogen bond to each other, resulting in a very
rigid structure.
- Cellulose is an important structural polysaccharide.
- It is the single most abundant organic compound on earth.
- It is the material in plant cell walls that provides strength and rigidity; wood is 50%
cellulose.
- Most animals lack the enzymes needed to digest cellulose, although it does provide
needed roughage (dietary fiber) to stimulate contraction of the intestines and thus help
pass food along through the digestive system.
- Some animals, such as cows, sheep, and horses, can process cellulose through the use
of colonies of bacteria in the digestive system which are capable of breaking cellulose
down to glucose.
- Ruminants use a series of stomachs to allow cellulose a longer time to digest.
- Some other animals such as rabbits reprocess digested food to allow more time for the
breakdown of cellulose to occur.
- Cellulose is also important industrially, from its presence in wood, paper, cotton,
cellophane, rayon, linen, nitrocellulose (gun cotton), photographic films (cellulose
acetate), etc.
Chitin
- Chitin is a polymer that can be found in anything from the shells of beetles to webs of
spiders.
- It is present all around us, in plant and animal creatures.
- It is sometimes considered to be a spinoff of cellulose, because the two are very
molecularly similar.
- Cellulose contains a hydroxy group, and chitin contains acetamide.
- Chitin is unusual because it is a "natural polymer," or a combination of elements
that exists naturally on earth.
- Usually, polymers are man-made. Crabs, beetles, worms and mushrooms contain large
amount of chitin.
- Chitin is a very firm material, and it helps to protect an insect against harm and
pressure.
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