CARBOHYDRATE – a polyhydroxyaldehyde or MONOSACCHARIDE – a carbohydrate that

polyhydroxyketone or a substance that gives cannot be hydrolyzed to a simpler compound.

their compunds on hydrolysis.
SACCHARIDE – a simpler member of the
carbohydrate family.
KETOSE – a monosaccharide containing a ketone
group.
GLYCOSIDE – a carbohydrate in which the –OH
on its anomeric carbon is replaced by –OR.
GLYCOSIDIC BOND – the bond from the
anomeric carbon or a glycoside to an –OR group.
ALDOSE – a monosaccharide containing an
aldehyde group.
ANOMERS – monosaccharides that differ in
configuration only at their anomeric carbons.
FURANOSE – a five-membered cyclic hemiacetal
form of a monosaccharide.

ALDITOL – the product formed when the C=O
group of a monosaccharide is reduced to a CHOH
group.
REDUCING SUGAR – a carbohydrate that
reacts with a mild oxidizing agent under basic
conditions to give an aldonic acid; the
carbohydrate reduces the oxidizing agent.
PENULTIMATE CARBON – the stereocenter of
a monosaccharide farthest from the carbonyl
group.
ANOMERIC CARBON – the hemiacetal carbon
of the cyclic form of a monosaccaride.
PYRANOSE - a six-membered cyclic hemiacetal
form of a monosaccharide.
DISACCHARIDE – a carbohydrate containg two
monosaccharide units joined by a glycosidic
bond.
OLIGOSACCHARIDE – a carbohydrate containg
from four to ten monosaccharide units, each
joined to the next by a glycosidic bond.
POLYSACCHARIDE – a carbohydrate containing
a large number of monosaccharide units, each
joined to the next by one or more glycosidic
bond.

Carbohydrates are the most abundant organic compounds in the plant world. The name
“carbohydrate” means hydrate of carbon. The simpler members of the carbohydrate family are often
referred to as saccharides.

Monosaccharides have the general formula CnH2nOn , with one of the carbons being the carbonyl
group of either an aldehyde or ketone. The most common monosaccharides have three to eight carbon
atoms. The suffix “-ose’ indicates that a molecule is a carbohydrate, and the prefixes “tri-,” “tetr-,”
“pent-,” and so forth indicate the number of carbon atoms in the chain.

Carbohydrates consist of carbon, hydrogen, and oxygen. The general empirical structure for
carbohydrates is (CH2O)n. They are organic compounds organized in the form of aldehydes or ketones
with multiple hydroxyl groups coming off the carbon chain. The building blocks of all carbohydrates are
the simple sugars called monosaccharides. A monosaccharide can be a polyhydroxy aldehyde (aldose) or a
polyhydroxy ketone (ketose).
 Both Aldose and Ketose are monosaccharides that can be differentiate as: Aldose is the
monosaccharide that contains Aldehyde group in its structure along with the carbon chain, whereas
ketose is the monosaccharide that contains ketone group along with the carbon chain.

An Aldehyde group is a compound A Ketone group is a functional group with

containg a functional group with the structure – the structure RC(=O)R’ , where R and R’ can be a
CHO, consisting of a carbonyl center ( a carbon variety of carbon-containing substituents.
double-bonded to oxygen) with the carbon atom
also bonded to hydrogen and to an R group.

Hawort Projections D- and L- Monosaccharides

A common way of representing the cyclic The configuration of carbohydrates as

structure of monosaccharides is the Haworth
Projection, named after the English chemist Sir
Walter N. Haworth. In Haworth Projection, a
five- or six-membered cyclic hemiacetel is
represented as a planar pentagon or hexagon.
The new carbon stereocenter created in forming
the cyclic structure is called anomeric carbon.
Stereoisomers that differ in configuration only
is called anomers. A six-membered hemiacetal
ring is indicated by the infix “-pyran-,” and the
five-membered hemiacetal ring is indicated by
the infix “-furan-.” The terms fuuranose and
pyranose are used because monosaccharide five-
and six-membered rings correspond to the
heterocyclic compounds furan and pyran.
well as those of amino acids and many other
compounds in biochemistry is commonly
designated by the D,L system proposed by Emil
Fisher in 1891. At that time, it was known that
one enantiomer of glyceraldehyde that has a
specific roation of +13.5°; the other has a
specific rotation of –13.5°. The reference point
is the stereocenter farthest from the carbonyl
group. Because this stereocenter is always the
next to the last carbon on the chain it is called
penultimate carbon. A D-monosaccharide has the
same configuration at its penultimate carbon as
D-glyceraldehyde, its –OH is on the right. A L-
monosaccharide has the same configuration at
its penultimate carbon as L-glyceraldehyde, its –
OH is on the left.
Fisher Projection Formula Conformation Representations

Chemists commonly used two-dimensional It is also known as Chair Conformation, it

representations called Fisher Projections to is the most stable conformation of a
show the configurations of carbohydrates. cyclohexane ring; all bond angles are
Sugars are shown in their open chain form by approximately 109.5°. In a chair conformation,
Fischer projections. This is when they form a the twelve C–H bonds are arranged in two
long chain of carbons in a line, rather than their different orientations. Six of them are called
cyclic form. The carbon atoms of the main chain axial bonds, and the other six are called
in the carbohydrate molecule are connected equatorial bonds. Axial bonds are parallel to the
vertically, while hydroxyl groups and hydrogen axis while the Equatorial bonds are
atoms are bonded horizontally. approximately perpendicular to the axis.

 Colorless, crystalline solid

 Soluble in water (good H–bonds between –

OH groups and water)

 Most are sweet to the taste

Formation of Glycosides Reduction to Alditols

Glycosides are formed when the anomeric The carbonyl group of a monosaccharide
(hemiac-etal or hemiketal) hydroxyl group of a can be reduced to a hydroxyl group by a variety
monosaccharide undergoes condensation with of reducing agents, including hydrogen in the
the hydroxyl group of a second molecule, with presence of a transition metal catalyst. The
the elimination of water. Formation reduction products are known as alditols.
of glycosides is an example of acetal formation,
which is a reaction between a hemiacetal group
and another hydroxyl group.
The linkage resulting from such a reaction is
known as a glycosidic bond.
Oxidation to Aldonic Acid. Reducing Sugars Oxidation to Uronic Acid

The Aldehyde group of an aldose can be Enzyme-catalyzed oxidation of the

oxidized, under basic conditions, to a
carboxylate group. Under these conditions, the
cyclic form of an aldose is in equilibrium with the
open-chain form, which is then oxidized by the
mild oxidizing agent. Any carbohydrate that
reacts with an oxidizing agent to form an aldonic
acid is classified as a reducing sugar.
primary hydroxyl group at C-6 of a hexose yields
a uronic acid.
Phosphoric Esters
Mono- and diphosphoric esters are
important intermediates in the metabolism of
monosaccharides. The phosphoric acid is a
strong acid, at the pH of cellular and
intercellular fluids, both acidic protons of a
phosphoric esters are ionized giving the ester
group a charge.

Disacharides

Disaccharide, also called double sugar, any substance that is composed of two molecules of
simple sugars called monosaccharides linked to each other. Disaccharides are crystalline water-
soluble compounds. The monosaccharides within them are linked by a glycosidic bond.

Maltose Lactose

Maltose derives its name from its Lactose is a principal sugar present in
presence of malt, the juice from sprouted barley milk. It makes up about 5 to 8 percent of human
and any other cereal grains. Maltose consists of milk and 4 to 6 percent of cow’s milk. It consists
two molecules of D-glucopyranose joined by a of D-galactopyranose bonded by a β-1,4-
glycosidic bond between C-1 of one unit and C-4 glycosidic bond to C-4 of D-glucopyranose.
of the other unit.
Sucrose

Sucrose is the most abundant

disaccharide in the biological world. It is
obtained principally from the juice of sugar cane
and sugar beets. In sucrose, C-1 of α-D-
glucopyranoseis joined to C-2 of D-
fructofuranose by an α1,2-glycosidic bond.

Oligosaccharides

A carbohydrate containing from four to ten monosaccharides units, each joined to the next by a
glycosidic bond.
 Raffinose

It can be found in beans, cabbage,

brussels sprouts, broccoli, asparagus, other
vegetables, and whole grains. Raffinose is a
trisaccharide composed of galactose, glucose,
and fructose. In raffinose,C-1 of α-D-
galactopyranose joined to C-1 of α-D-
glucopyranose is joined to C-2 of D-
fructofuranose.

Polysaccharides

Polysaccharides consists of large numbers of monosaccharide units joined together by glycosidic

bonds. Three important polysaccharides, all made up of glucose units, are starch,glycogen, and cellulose.

Glycogen Cellulose

Glycogen is the energy-reserve Cellulose, the most widely distributes

carbohydrate for animlas. Glycogen is a
6
branched polysaccharide of approximately 10 D-
glucose units joined by a α-1,4- and α-1,6-
glycosidic bonds.
plant skeletal polysaccharide, constitutes almost
half of the cell wall material of wood. Cellulose is
a linear polysaccharide of D-glucose units joined
by β-1,4-glycosidic bonds.

Starch. Amylose and Amylopectin

Starch is used for energy storage in

plants. It is found in all plants seeds and tubers
and is the form in which glucose is stored for
later use. Starch can be separated into two
principal polysaccharides: amylose and
amylopectin. Amylose is composed of continuous,
unbranched chains up to 4000 D-glucose units
joined by α-1,4-glycosidic bonds. Amylopectin
contains chains up to 10,000 D-glucose joined by
α-1,4-glycosidic bonds.
Acidic Polysaccharides

Acidic polysaccharides are a group of polysaccharides that contain carboxyl groups and/or
sulfuric ester group. These compounds play important roles in the structure and function of connective
tissues, the matrix between organs and cells that provides mechanical strength and also filters the flow
of molecular information between cells.

Hyaluronic Acid Heparin

Hyaluronic acid is the simplest acidic Heparin is a heterogeneous misture of

polysaccharide present in connective tissue.
Hyaluronic acid is composed of D-glucuronic acid
linked by a β-1,3-glycosidic bond to N-acetyl-D-
glucosamine, which is in turn linked to D-
glucuronic acid by a β-1,4-glycosidic bond.
variably sulfonated polysaccharide chains. This
acidic polysaccharide is synthesized and stored
in mast cells of tissues, particularly the liver,
lungs, and gut. Heparin has many biological
functions, best known and understood of which
is its anticoagulant activity. The repeating
monosaccharide units of heparin are D-
glucosamine, D-glucuronic acid and L-ioduronic
acid bonded by a combination of α-1,4-and β-1,4-
glycosidic bonds.