CARBOHYDRATES

• Definition. Carbohydrates are defined chemically as

polyhydroxy aldehydes or ketones, or compounds which
yield these derivatives on hydrolysis.

• Carbohydrates comprises of Carbon, Hydrogen and

Oxygen.
• That’s why carbohydrates are also called Hydrates of
Carbon.
• Their General formula is Cn(H2O)n.

• Ribose C5H10O5 Glucose C6H12O6

 CLASSIFICATION OF
CARBOHYDRATES

• Have been classified into 4 main

groups
• – Monosaccharides
• – Disaccharides
• – Oligosaccharides
• – Polysaccharides
 1. MONOSACCHARIDES

• Carbohydrates which can’t further bebroken down

into simpler units by acid hydrolysis
• Usually have 3-9 carbon atoms
• Further sub-classified into aldoses and ketoses
• Exact name is based on
– number of carbons atoms
– presence of aldehyde or ketone groups
i.e aldotriose or ketotriose
• Monosaccharides also include derivatives of
above mentioned monosaccharides e.g.
amino sugars, sugar alcohols, sugar acids.
 2. DISACCHARIDES

• Formed when two monosaccharides undergo a

condensation reaction which involves the
elimination of a small molecule, such as water.

Glucose Fructose
 IMPORTANT DISACCHARIDES

• Maltose- Glucose + Glucose

• Sucrose- Glucose + Fructose
• Lactose- Glucose + Galactose
 3. OLIGOSACCHARIDES

• Greek word oligos, meaning "a few", and sacchar

which means "sugar“
• Saccharide polymers containing a small number
(typically three to ten) Monosaccharides.

• For example
• Raffinose, Stachyose and Verbascose (in beans,
peas, lentils, cabbage, whole grains)
• Lactosucrose (produced from lactose and sucrose)
 Important Oligosaccharides

• 1. Raffinose Glucose + Frucotse + Galactose

• 2. Stachyose Glucose + Frucotse + Galactose+ Galactose
• 3. Verbascose Glucose + Frucotse + Galactose+ Galactose+
Galactose
 4. POLYSACCHARIDES

• Polymeric carbohydrate structures, formed by repeating

units (either mono- or di- saccharides) joined together by
glycoside bond
• Such structures are often linear, but may contain various
degrees of branching
• Polysaccharides have a general formula of (C6 H10O5)n
• Not sweet, hence called non-sugars

• Starch, glycogen, agar,

 IMPORTANCE OF CARBOHYDRATES

• Provide major source of energy (4.1C)

• Supporting tissues in plants
• Serve also as stored forms of energy as
glycogen in liver and muscles
• Protein sparing action
• Reduce breakdown of fatty acids and
preventing ketosis
Flavoring and Sweetening agents
Dietary fiber (Cellulose)
Important components of brain cells as
neuraminic acids, cerebrosides (Glycolipids)
and gangliosides
Important component of nucleic acids as
pentose sugars - ribose and deoxyribose
Function as physiological anticoagulant
(Heparin)
Carbohydrates are also used in Pharmacy
Preparation of syrup (Sucrose).
As diluents and binders (Starch, Lactose,
Gum).
For Sugar-coating (Liquid Glucose).
Preparation of sterile I/V solutions
(Dextrose).
Preparation of Infants‘ food (Starch,
Dextrin).
ISOMERISM
 1. FUNCTIONAL GROUP ISOMERISM

• Same molecular formula but different functional

groups.
• Aldose-Ketose Isomerism
• For example: Fructose is a functional group
isomer of glucose.
Glceraldehyde Dihydroxyacetone
(Aldose) (Ketose)
 2. STEREOISOMERISM

• Compounds with same molecular formula but

different arrangement of atoms in space
(configuration) are called as stereoisomers and
this phenomenon is called as stereoisomerism.
Two such isomers of glceraldehyde D-Glyceraldehyde
and L-Glyceraldehyde

Two such isomers of glucose—D-Glucose and L-

Glucose
• The number of isomers depend upon the
number of asymmetric carbon atoms in the
compound.
• The number of these isomers = 2n
• (Where n is the number of asymmetric
carbon atoms)
• Stereoisomers are mirror image of each
other but can not be superimposed on each
other.
• Stereoisomers are also called as
enantiomers.
 3. OPTICAL ISOMERISM
• Compounds have same molecular formula but differ in
the direction of rotation of plane polarized light (PPL).
• The presence of asymmetric carbon atom causes plane
polarized light to rotate.
• Optical isomers or enantiomers
• Dextoroation, d (+)
• Levorotation, l (-)
• D Glucose – D (+) Glucose
• D Fructose- D (-) Fructose
en a beam of plane polarized light is passed through the solution of
a carbohydrate.

Rotation of light to right Rotation of light to left

Dextro rotatory (+) (d) Levo rotatory (-) (l)

Glucose is Dextro rotatory (+) (d) D-Fructose is Levo rotatory (-)

 4. EPIMERISM

• Sugars which differ from each other with respect

to single carbon atom.
• D-Galactose and D-Mannose are epimers of D-
Glucose.
 5. ANOMERISM

• Anomers are cyclic monosaccharides that dfifer

in the configuration of C-1 (in case of Aldose)or
C-2 (in case of Ketose).
 FISCHER PROJECTION

• Definition. Fischer projection is defined as the method of

presenting three-dimensional organic molecules in two-
dimensional structures on a two-dimensional plane such
as a paper.

• Horizons and vertical lines are used to represent the

bonds and the intersection of a horizontal and a
vertical line represents the central carbon atom.
• The horizontal lines represent the bonds point out of
the plane, and the vertical lines represent the bonds
that point behind the plane.
• Conventions
• There are a few rules to be followed while the Fischer
projection is to be used:
The carbon atoms in a chain are represented on a
vertical line
The carbon atoms may not be represented by the letter
itself and the intersection of the two lines will depict the
carbon atom at the center.
All the horizontal lines of a Fischer projection are
projected towards the viewer and all the vertical lines
are projected away from the viewers.
Isomers of different sugars in organic chemistry are the
most common representations of Fischer projection.
• Applications. Fischer projections are used to
represent molecules and compounds in
biochemistry and organic chemistry, especially
structures of monosaccharides and amino acids.
• Using Fischer projection, the structure of
monosaccharides can be visualized easily.
• Apart from showing structures of organic
compounds, Fischer projection can also be used to
differentiate between L-sugars and D-sugars. L-
sugars are depicted by hydrogen atoms on the
right and hydroxyl groups on the left, and D-sugars
are presented by hydrogen atoms on the left and
the hydroxyl groups on the right.
 CYCLIC STRUCTURES AND
ANOMERIC FORMS
• Although Fischer projections are useful for
presenting the structures of particular
monosaccharides and their stereoisomers ,
they ignore one of the most interesting facts
of sugar structure
—the ability to form cyclic structures with
formation of an additional asymmetric
centre
 HAWORTH PROJECTION

• Definition. The Haworth projection is a method

used to draw cyclic monosaccharides (or sugars).
The Haworth structure shows the bonds on the
compound and the 3D orientation of the bonds.
• A Haworth projection differs from a Fischer
projection in that it is used to represent the
carbohydrate in its cyclical form. This is especially
useful for sugars which have a ring structure. It
was devised by the English chemist Sir Norman
Haworth who expanded on the work of Fischer,
characterizing many more carbohydrates.
• Alcohols react readily with aldehydes to form
hemiacetals
• A British Chemist Sir Norman Haworth showed
that the linear form of glucose and other
aldohexoses could undergo a similar
intramolecular reaction to form a cyclic hemiacetal
• The resulting six- membered, oxygen-containing
ring is similar to pyran and is designated as
pyranose-glucopyranose. The reaction is catalysed
by acid or base and is readily reversible

Pyran
• An analogous intramolecular reaction of a
ketose sugar such as fructose yields a cyclic
hemiketal
• The five-membered ring thus formed is
reminiscent of furan and is referred to as a
furanose
• The cyclic pyranose and furanose forms are
the preferred structures for monosaccharides
in aqueous solution
 MUTAROTATION

• Definition. Change in specific optical rotation of a

sugar representing the interconversion of ⍺ and β
forms to an equilibrium mixture.
• When a sugar is first dissolved in water and the
solution is put in optical path so that plane polarized
light is passed, the initial optical rotation shown by the
sugar gradually changes until a constant fixed rotation
characteristic of the sugar is reached. This pheno-
menon of change of rotation is called as
mutarotation.
•
• When the ⍺ D-glucose is dissolved in water, at first, it
exhibits a specific rotation of +112.2 °, but
this changes with time to +52.6 °.
• The same happens with the β forms of D-glucose
where the specific rotation changes from +18.7 ° to
+52.6 °.

• It is due to the fact that on being disssolved in water,

the glucose molecules go on changing from one form
to another, each having a different optical rotation.
• At equilibrium, the mixture is composed of 37% of the
ɑ anomer, 63% of the β anomer, and only trace
amounts of the acyclic hydroxy aldehyde.
• The mechanism of muta- rotation probably involves
opening of the hemiacetal ring to form traces of the
aldehyde form, and then recondensation to the cyclic
forms. The aldehyde form is extremely unstable and
exists only as a transient intermediate.
• Monosaccharides
• 1.Glucose
• It is an aldohexose with the molecular formula C6H12O6.
• It is the main sugar in human body.
• Sucrose is the most common source of glucose.
• It is the first line of nutrition for the production of
energy through glycolosis and citric acid cycle.
• Among all carbohydrates brain utilizes only glucose for
its energy requirement.
• Low level of glucose may cause hypoglycemia.
• Normal blood glucose level is: 100 to 120 mg/dl.
• If glucose is present in excess it is converted into
glycogen which is stored in liver and muscles.
• 2. Fructose
• It is a ketohexose. It is the sweetest of all sugar.
• The most common source of fructose is sucrose.
• Pure honey is made up of fructose only.
• Fructose is converted to glucose in liver.
• 3. Galactose
• It is an aldohexose.
It is epimer of glucose and is present in lactose.
• It readily converts into glucose and is used by the
body for the development of brain tissues
(cerebrosides and gangliosides).
• 4. Mannose
• It is an aldohexose and is convertd to glucose in vivo.
• Disaccharides
• Maltose
• It is a disaccharide formed from two units of glucose
joined with an α(1→4) linkage.
• Also known as Fruit sugar.
• Maltase hydrolyzes maltose and produce two glucose
molecules.
• 2. Lactose
• Lactose is a disaccharide of galactose and glucose
and have a
• ß-1,4-glycosidic bond (between ß-galactose and ß-
glucose).
• It is also called Milk sugar.
• Lactase present in intestine, hydrolyzes lactose and
yields glucose and galactose.
• 3.Sucrose
• It is a disaccharide formed by the linkage of Glucose and Fructose.
• It has an α,β-1,2-glycosidic bond (between α-glucose and β-
fructose).
• It is also known as Cane sugar and is commonly known as Table
sugar.
• Sucrose is very soluble and very sweet.
• Sucrase present in intestine, hydrolyzes sucrose into glucose and
fructose.
A. Homopolysaccharides:
•Upon hydrolysis, these yield only one type of monosaccharide
units.
•Animal source: Glycogen.
•Plant source: Starch, cellulose.
•All of these contain glucose
• Starch:
• Starch is a polymer of glucose and occurs in many
plants as storage foods.
• It is of two types i.e. amylose and amylopectin.
• Source:
• Starch is the most abundant and widely distributed plant
substance next to cellulose and hemicellulose.
• The most common commercial sources are the
graminaceous fruits (e.g. rice and wheat ), maize and
potato tubers
• Amylose:
• • Composed of α-glucose in a continuous (un-
branched) chain.
• Has α-1,4 glycosidic bond between α-glucose units
(250-4000 units).
• Amylopectin:
• Has α -1,4 glycosidic bond between glucose
units.
• Has α -1,6 glycosidic bond to branches the
glucose units.
• 2. Glycogen
• It is present mainly in liver and muscles, where it act
as a storage polysaccharides for glucose.
• Also known as animal starch. It is similar to
amylopectin (more highly branched-every 10-15
units).
• During fasting, liver glycogen maintains blood
glucose level.
• Cellulose
• Cellulose, a major constituent of plant cell walls, consists of
long linear chains of glucose with ß-1,4 linkages.
• Humans don’t have cellulase hence cannot digest cellulose.
• It is present mainly in plants.
• Sources: Whole grain cereal, breads, fruits, vegetables and
legumes.
• Heteropolysaccharides
• Agar
• Gum
• Pectin
• Agar is obtained from red algae and seaweed
such as Gracilaria and Gelidium.
• s found in nature, agar is a mixture of two
components, the linear polysaccharide agarose
and a heterogeneous mixture of smaller
molecules called agaropectin
• It is used in microbiology,
• Making gelly, desserts, custards
• Gum is one of the herbal
biopolysaccharides, which is extracted
from Acaccia arabica.
• Consists of branched polysaccharide-based
structure having various sugars—such as
arabinose, rhamnose, galactose,
glucuronic acid, etc.
• Used in printing, paints, glues.
• Thickening agent in chewgum.
• Pectin is heteroploysaccharides obtained
from fruits.
• Pectins, also known as pectic
polysaccharides, are rich in galacturonic
acid.
• Galactsoe, arabinose, rhamnose are also
present.
• The main use for pectin is as a
gelling agent, thickening agent and
stabiliser in food.
Aldaric acid
Bromine water

Aldonic acid
• 3-Formation of Amino Sugars
• A hydroxyl group of monosaccharide can be replaced
by an amino group forming an amino sugar.

NH3

-H2O
Amino group
• 4. Deoxy Sugars
• These are monosaccharides in which -OH is
replaced with H.
• E.g 2-deoxyribose which is constituent of DNA.
 CHEMICAL PROPERTIES

1.Reduction
2. Oxidation
3. Fehling‘s solution test
4. Tollen‘s reagent test
5. Benedict‘s test
6. Barfoed‘s test General formula Aldosugars
7. Molish‘s test Ketosugars
Trioses Glyceraldehyde
8. Fromation of osazones Dihydroxyacetone
Tetroses Erythrose
Erythrulose
Pentoses Ribose
• 1. Reduction to form sugar alcohols
• Both aldoses and ketoses may be reduced at their aldehyde or
ketone group to form polyhydroxy alcohols.
• 2. Oxidation
With mild oxidizing agents like bromine water, glucose is oxidized
to glucuronic acid.
 3.FEHLING‘S SOLUTION TEST

• Fehling’s test is a chemical test used to differentiate between reducing and non-
reducing sugars.
• The carbohydrates having free or potentially free carbonyl groups (aldehyde or ketone)
can act as reducing sugars.
• The Fehling’s solution appears deep blue in color and consists of copper sulfate mixed
with potassium sodium tartrate and strong alkali, which is usually sodium hydroxide.
 4. TOLLEN‘S REAGENT TEST

• Tollens’ test, also known as silver-mirror test, is a qualitative

laboratory test used to distinguish between an aldehyde and a
ketone.
• It exploits the fact that aldehydes are readily oxidized ,
whereas ketones are not.
• Tollens’ test uses a reagent known as Tollens’ reagent, which is
a colorless, basic, aqueous solution containing silver ions
coordinated to ammonia [Ag(NH3)2+
• When glucose is heated with tollen‘s reagent, there is a deposit
of silver on the walls of the test tube to form silver mirror.
 5. BENEDICT‘S TEST

• Benedict’s test is a chemical test that can be used to check for

the presence of reducing sugars in a given analyte.
• Therefore, simple carbohydrates containing a free ketone or
aldehyde functional group can be identified with this test.
• The test is based on Benedict’s reagent (also known as
Benedict’s solution), which is a complex mixture of sodium
citrate, sodium carbonate, and the pentahydrate of copper(II)
sulfate.
 6. BARFOED‘S TEST

• To detect reducing carbohydrates.

• To distinguish reducing monosaccharides from disaccharides.
• The Barfoed reagent is made up of copper acetate in a dilute
solution of acetic acid.
 7.MOLISH‘S TEST

• Molisch’s test is a chemical test which is used to check for the

presence of carbohydrates in a given analyte.
• Molisch’s test involves the addition of Molisch’s reagent (a
solution of ∝-naphthol in ethanol) to the analyte and the
subsequent addition of a few drops of concentrated H2SO4 (
sulphuric acid) to the mixture.
• The formation of a purple or a purplish-red ring at the point of
contact between the H2SO4 and the analyte + Molisch’s
reagent mixture confirms the presence of carbohydrates in the
analyte
8. Formation of osazones

Heating sugar solution with phenylhydrazine results in the

formation of phenylosazones which are yellowish crystalline
compounds.

Glucose+ 3(C6H5NHNH2) Glucosazone+C6H5NH2+ NH3+2H2O

9. Formation of glycosides
• Glycoside, any of a wide variety of naturally occurring substances in which a
carbohydrate portion, is combined with a hydroxy compound (alcoholic residue) which
is called aglycone and is non carbohydrate.
• 10. formation of esters
• Hydroxyl groups of sugars can be esterified to give esters such as phosphates,
acetates, propionates, stearates.
• Sugar phosphates (esters of sugars with phophoric acid) are of great biological
importance.
• Glucose-6-phosphate
• 11. formation of amino sugars
• A hydroxyl group of monosaccharide can be replaced by an amino group forming an
amino sugar.
SOME IMPORTANT CARBOHYDRATES

• Monosaccharides
• 1.D-glucose

• Also called as grape sugar.

• Dextro rotatory and widely distributed in nature.
• Occurs in combination with other sugars.
• Commercially obtained from starch.
• 60-100 mg/dl in blood.
• On reduction, glucose forms alcohol, sorbitol.
• On oxidation, glucose forms sugar acids.
• 2. D-fructose

• Also called as fruit sugar.

• Occurs in plant kingdom as such or in combination with glucose.
• Small amounts also present in animal tissues.
• B. Disaccharides

• Also called as saccharose and is common table sugar.

• On hydrolysis, yields D-glucose and D-fructose.
• Does not contain free anomeric carbon, does not possess
reducing properties.
• Does not form osazones
• Does not show the property of mutarotation.
• Sucrose is dextrorotatory.
• 2. Maltose

• Formed o glycosidic linkage between one molecule of ⍺-D-

glucose with another molecule of ⍺-D-glucose with the
elimination of water molecule.

CH2OH CH2OH
• 3. lactose

• Also called as milk sugar.

• Least sweet.
(O-glycosidic linkage Β-D galactose and D-glucose)
• Polysaccharides
• Starch
• Main form in which carbohydrates are ingested by man.
• Two types of polysaccharide units, amylose and amylopectin.
• Both are made up of ⍺-D glucose.
• Amylose
• Straight chain.
• Gives blue colour with iodine.
• Amylopectin

• Branched chain.
• Forms 70-80 percent starch.
• Two types of linkages. (about 90 percent, 1-4 linkage as in
amylose)
• (1-6 linkage)
Homopolysaccharides (homoglycans):
Polymer of same monosaccharide units.

Examples—Starch, glycogen, cellulose, dextrans, inulin.

Heteropolysaccharides (heteroglycans):
Polymer of different monosaccharide units or their
derivatives.

Example—Mucopolysaccharides (glycosaminoglycans).
• pectin, lignin