2.

Carbohydrates
Mubashra Gul
lecturer
• 2. Carbohydrates
 CARBOHYDRATES
• CARBOHYDRATES ARE ALDEHYDE OR KETONE DERIVATIVES OF
POLYHYDRIC ALCOHOLS
Classification
• Monosaccharide
• Disaccharides
• Oligosaccharides
• Polysaccharides
1. homopolysaccharides
2. heteropolysaccharides
 Monosaccharides
• Monosaccharides are those sugars that cannot be hydrolyzed into
simpler carbohydrates
• aldoses or ketoses, depending upon whether they have an aldehyde
or ketone functional group.
• Aldehyde and ketone groups are called carbonyl groups
• Aldehyde group present at the end.
• Ketone group is not present at the end but at some where else
Monosaccharides Are Aldoses and Ketoses

• Monosaccharides are colorless, crystalline solids,

• Freely soluble in water but insoluble in nonpolar
solvents,
• Most have a sweet taste.
• carbon atoms at backbone are linked by single bonds.
• In the open-chain form, one of the carbon atoms is
double-bonded to an oxygen atom to form a carbonyl
group; each of the other carbon atoms has a hydroxyl
group.
• Monosaccharides with four, five, six, and seven carbon
atoms in their backbones are called, respectively tetroses,
pentoses, hexoses, and heptoses.
• D-glucose is an aldohexose and D-fructose is the
ketohexose.
Aldoses and ketoses
Properties in Reference to Glucose
• General Asymmetric carbon: A carbon atom to which four different
atoms or groups of atoms are attached is said to be asymmetric.
Van’t Hoff’s rule of ‘n’:
The number of possible isomers of any given compound depends upon
the number of asymmetric carbon atoms the molecule possesses.
Asymmetric carbon According to Van’t Hoff’s rule of ‘n’; 2n equals the
possible isomers of that compound, where, n = represents the number
of asymmetric carbon atoms in a compound.
Stereoisomerism
The presence of asymmetric carbon atoms in a compound gives rise to the formation
of isomers of that compound.
Such compounds which are identical in composition and differs only in spatial
configuration are called stereoisomers.
Two such isomers of glucose, D-Glucose and L-Glucose are mirror image of each other.
D-Series and L-Series: The orientation of the H and OH groups around the carbon
atom just adjacent to the terminal primary alcohol carbon, e.g. C atom 5 in glucose
determines the series.
When the – OH group on this carbon is on the right, it belongs to D-series, when the –
OH group is on the left, it is a member of L-series.
Most of the monosaccharides occurring in mammals are D-sugars, and the enzymes
responsible for their metabolism are specific for this configuration.
Optical activity:
Presence of asymmetric carbon atoms also confers optical activity on the
compound.
When a beam of plane-polarised light is passed through a solution exhibiting
optical activity, it will be rotated to the right or left in accordance with the type of
compound, i.e. the optical isomers or enantiomorphs;
• when it is rotated to right, the compound is called • Dextrorotatory (D or + sign),
• when rotated to left, the compound is called • Laevorotatory (I or – sign).
Racemic: When equal amounts of dextrorotatory and laevorotatory isomers are
present, the resulting mixture has no optical activity, since the activities of each
isomer cancels each other. Such a mixture is said to be Racemic. Resolution: The
separation of optically active isomers from a racemic mixture is called resolution.
Cyclization of glucose
As the two reacting groups aldehyde and alcoholic group belong to the
same molecule, a cyclic structure takes place. If the open-chain form of
D-Glucose, which may be called as Aldehydo-D-Glucose is taken, and
condense the aldehyde group on carbon-1, with the alcoholic-OH group
on carbon-5, two different forms of glucose are formed.
When the OH group extends to right, it is α -D-Glucose.
and when it extends to left, it is β -D-Glucose.
Anomers and anomeric carbon
Generally, hemiacetal formation in glucose develop a new chiral center,
(formed at the former carbonyl carbon) which is now called the
anomeric carbon.
The two cyclic compounds, α and β have different optical rotations, but
they will not be same because the compounds as a whole are not
mirror-images of each other.
• Hemiacetal (aldehyde and alcohol)
• Hemiketal  (Ketone and alcohol)
 Epimers
Epimers: Isomers differing as a result of variations in configuration of
the —OH and —H on carbon atoms 2, 3, and 4 of glucose are known as
Epimers.
Biologically, Epimers of glucose are mannose (epimerized at carbon 2)
and galactose (epimerized at carbon 4).
 Disaccharides
• Disaccharides are condensation products of two monosaccharide
units; examples are maltose and sucrose.
• Glucose +glucose_________maltose
• Glucose +galactose________lactose
• Glucose +fructose_________sucrose
• Joined through o-glycosidic linkage
PROPERTIES OF DISACCHARIDES
1. Maltose:
Maltose or malt sugar is an intermediary in acid hydrolysis of starch and
can also be obtained by enzyme hydrolysis of starch. In the body,
dietary starch digestion by Amylase in gut yields maltose, which
requires a specific enzyme maltase to form glucose. It is a rather sweet
sugar and is very soluble in water. Since it has one aldehyde ‘free’ or
potentially free .it has reducing properties, and forms characteristic
osazones, which has characteristic appearance ‘Sunflower’ like.
On hydrolysis Maltose yields two molecules of glucose.
2. Lactose:
• Lactose is milk sugar and found in appreciable quantities in milk to the
extent of about 5 per cent and occurs at body temperature as an
equilibrium mixture of the α and β forms.
• It is not very soluble and is not so sweet. It is dextrorotatory. Specific
enzyme which hydrolyses is lactase present in intestinal juice. On
hydrolysis it yields one molecule of D-Glucose and one molecule of D-
Galactose.
• Because it contains galactose as one of its constituents, it yields mucic
acid on being treated with Conc HNO3 after hydrolysis. As one of the
aldehyde group is free or potentially free it has reducing properties and
can form osazones(Lactosazone).
3. Sucrose
Ordinary table sugar is sucrose. It is also called as ‘Cane sugar’, as it can
be obtained from sugarcane. Also obtained from sugar beet, and sugar
maple. Also occurs free in most fruits and vegetables, e.g. pineapples,
and carrots.
It is very soluble and very sweet and on hydrolysis yields one molecule
of D-Glucose and one molecule of D-Fructose. The specific enzyme
which hydrolyses sucrose is sucrase present in intestinal juice.
As both aldehyde and ketone groups are linked together (α1 → 2), it
does not have reducing properties, and cannot form osazones.
4. Lactulose:
• A ketodisaccharide structure, It is O-α-D-galactopyranosyl-(1→4)-β-D-
fructofuranose.
• Source: Heated milk (small amounts).
• Mainly obtained synthetically.
• It is used clinically in medicine as an osmotice laxative
 Oligosaccharides
• Oligosaccharides are condensation products of three to ten
monosaccharides. Most are not digested by human enzymes.
• On hydrolysis yield 2-10 monosaccharides
• Α dextrin contain 8 glucose units.
• Maltotriose contain 3 glucose units.
 Polysaccharides
• Polysaccharides are condensation products of more than ten
monosaccharide units
• 100-1000 units of monosaccharides.
• Stores of fuels e.g glycogen, starch.
• Structural element of cell.
 homopolysaccharides
One hydrolysis yield only one type of monomer
• Starch
• Glycogen
• Cellulose
• Dextran biopolymer produce by certain bacteria
1. Starch
• Starch is a homopolymer of glucose forming an α-glucosidic chain, called a
glucosan or glucan. It is the most important dietary carbohydrate in cereals,
potatoes, legumes, and other vegetables.
• The two main constituents are amylose (15–20%),(6 glucose units per each
helix) which has a nonbranching helical structure, and amylopectin (80–85%),
which consists of branched chains composed of 24–30 glucose residues
united by α-1, 4 linkages in the chains and by α-1, 6 linkages at the branch
points.
• The glycemic index of a starchy food is a measure of its digestibility, based on
the extent to which it raises the blood concentration of glucose compared
with an equivalent amount of glucose or a reference food such as white bread
or boiled rice.
STRUCTURE OF STARCH
2.Glycogen
is the storage polysaccharide in animals and is sometimes called animal
starch. It is a more highly branched structure than amylopectin with
chains of 12–14 α D -glucopyranose residues (in α 1 ,4 glucosidic
linkage) with branching by means of α 1,6 glucosidic bonds.
3. Inulin
is a polysaccharide of fructose (and hence a fructosan) found in tubers
and roots.
4. Dextrins
Dextrin are intermediates in the hydrolysis of starch.
5. Cellulose
Cellulose is a polymer of glucose. It is not hydrolyzed
readily by dilute acids, but heating with fairly high
concentrations of acids yields, the disaccharide
Cellobiose and D-Glucose. Cellobiose is made up of two
molecules of D-Glucose linked together by β -Glucosidic
linkage between C1 and C4 of adjacent glucose units.
 Heteropolysaccharides
• This is very large group containing 2 or more type of monosaccharides
derivatives along with other molecules
1. Glycos-amino-glycans or mucopolysaccharides
• hyaluronic acid
• chondroitin sulfate
• heparin
2. Glycoconjugates
Proteoglycan
Glycoprotein
glycolipids
3. Mucilages agar, vegetable gum and pectin
Glycosaminoglycans
Glycosaminoglycans (mucopolysaccharides) are complex
carbohydrates containing amino sugars and uronic acids. They may be
attached to a protein molecule to form a proteoglycan. Proteoglycans
provide the ground or packing substance of connective tissue. They
hold large quantities of water and occupy space, thus cushioning or
lubricating other structures, because of the large number of —OH
groups and negative charges on the molecule which, by repulsion, keep
the carbohydrate chains apart.
Examples are hyaluronic acid, chondroitin sulfate, and heparin
1. Hyaluronic Acid
A sulphate free mucopolysaccharide. It was first isolated from vitreous
humour of eye. Later it was found to be present in synovial fluid, skin,
umbilical cord, haemolytic streptococci and in rheumatic nodule. It
occurs both free and salt-like combination with proteins and forms so
called ground substance of mesenchyme, an integral part of gel-like
ground substance of connective and other tissues.
Composition:
It is composed of repeating units of N-acetyl glucosamine and D-
Glucuronic acid. On hydrolysis, it yields equimolecular quantities of D-
Glucosamine, D-Glucoronic acid and acetic acid.
2. Chondroitin Sulphates;
They are principal MPS in the ground substance of mammalian tissues
and cartilage. They occur in combination with proteins and are called as
Chondroproteins. Four chondroitin sulphates have been isolated so far.
They are named as chondroitin SO4 A, B, C and D.
3. Heparin
It is also called α -Heparin. It is an anticoagulant present in liver and it is
produced mainly by mast cells of liver (Originally isolated from liver). In
addition, it is also found in lungs, thymus, spleen, walls of large arteries,
skin and in small quantities in blood.
Structure:
It is a polymer of repeating disaccharide units of D-Glucosamine (Glc N)
and either of the two uronic acids-D-Glucuronic acid (Glc UA) and L-
Iduronic acid (IDUA).
Importance of carbohydrates
• Carbohydrates are used in pharmacy:
• for the preparation of simple syrup( sucrose). as diluents&
binders for the preparation of tablets(lactose, starch, gums)
& for coating sugar-coated tablets(liquid glucose).
• for preparation of infants’ food(starch & dextrin). for
preparation of sterile iv solutions(dextrose). In anti –diarrhea
drugs (pectin).
• As laxatives (mucilage, lactulose), antacids(sucral fate) or
diuretic drugs (manitol & sorbitol).
• as emulsifying agents(gums).
• as nutrient media for both bacteria and tissue cultures (agar).
• In the preparation of surgical dressing(cellulose) &
plasters( gums).
• In the preparation of surgical dressing(cellulose) & plasters( gums).
• Some carbohydrate derivatives have various therapeutic use such as
ascorbic acid, glucosamine, dextran and others.
• Uses of sucrose in Pharmaceutical industries, sucrose is used in syrup
preparation and tablet manufacture.
• It is used as nutrient and demulcent.
• Food is obtained from Starch.
• Cellulose is the source of clothes in the form of cotton, rayon, linen &
shelter materials like wood is also obtained from cellulose.
• GLUCOSE serve as instant source of energy.
• It serves as starting material for the preparation of vitamin C. It finds extensive
applications in the pharmaceutical preparations as tonicity agents, tablet binders &
diluents.
• It is also used in the manufacture of confectionary, jams, syrups.
• SUCROSE is an important source of sweetening agent & food. It is also used as
preservative for fruit products.
• LACTOSE is an ingredient of foods especially for children & is also employed as
diluent & excipient for compressed tablets & capsules.
• MALTOSE is an important disaccharide present in germinating seeds used in brewing,
soft drinks, food industry.
• STARCH in addition to providing food, is widely used in pharmacy as diluent,
disintegrant, binder, adhesive, absorbent, suspending agent & emulsifying agent.
• DEXTRIN is used as diluents for tablets & capsules.