MONOSACCHARIDES -

ISOMERISM; ANOMERISM;
SUGAR DERIVATIVES,
DISACCHARIDES, AND
POLYSACCHARIDES
Presented By : Hudha K
Josiyamol Mathew
Karthikeyan SI
 OVERVIEW
Introduction Structure of Types of
Disaccharides Polysaccharides
Monosaccharides
Examples of Functions of
Isomerism Disaccharides Polysaccharide
Polysaccharides Conclusion
Sugar Derivatives
Characteristics of Reference
Disaccharides Polysaccharides
 INTRODUCTION

Carbohydrates are fundamental biomolecules that play critical roles in the structure
and function of living organisms.The carbohydrates are sometimes referred to as
The saccharides. Carbohydrates are divided into 3 major groups based on the
Degree of polymerization: monosaccharides,disaccharides and Polysaccharides.
Monosaccharides are the building blocks of more complex carbohydrates.
Disaccharides are formed by the linkage of two monosaccharides through glycosidic
bonds.These compounds, such as sucrose and lactose, are essential for energy
storage and transfer in living organisms. Finally,
polysaccharides, the most complex carbohydrates, consist of long chains of
monosaccharide units.They serve various structural and storage functions
exemplified by cellulose in plants and glycogen in animals.
 MONOSACCHARIDES

• Those carbohydrates such as glucose and fructose that

cannot behydrolyzed into simpler compounds are called
simple sugars
• Monosaccharides( are the building blocks of more complex
carbohydrates such as disaccharides and polysaccharides

These simple sugars are

• Colourless
• Crystalline solids that are
• Soluble in water and insoluble in a nonpolar solvent.
• The general formula for representing monosaccharide
structure is Cn(H2O)n or (CH2O)n.
 CLASSIFICATION

FUNCTIONAL GROUPS
Aldoses and ketoses
• aldoses or aldehyde-containing monoses (R-CHO)
• Glucose, galactose, mannose, erythrose, talose, etc. are aldoses.
Erythrulose, xylulose, ribulose, fructose, sorbose, etc. are ketoses.
• The carbonyl group is attached to the C-1 in aldoses
• So, oxygen forms a double bond with C-1(ultimate carbon)in aldoses,
• ketone-containing monoses are called
ketoses
• Erythrulose, xylulose, ribulose,fructose,
sorbose,
etc. are ketoses
• The carbonyl group is attached to the C-2 In
ketoses
• oxygen forms a double bond with C-2
(penultimate carbon) in ketoses.
• ketoses as the derivatives of
dihydroxyacetone .
C ARBON CHAIN LENGTH

• Monosaccharides usually have 3 to

7 carbon atoms and an aldehyde
or ketone function.
• Based on the number of carbon
atoms, monosaccharides can be
classified in to
 CHEMIC AL PROPERTIES

1.Glycosidic bonding
Monosaccharides can form glycosidic bonds through a
dehydration reaction between the hydroxyl group of one
monosaccharide and the anomeric carbon of another.
Example: Glucose and fructose can form sucrose via an α-
1,2-glycosidic bond.
2.Reducing Properties
Monosaccharides, particularly aldoses (like glucose), have a
free aldehyde group in their open-chain form that can act as
a reducing agent. Ketoses (like fructose) can also act as
reducing sugars after tautomerization to aldoses.
Example: Glucose can reduce copper(II) ions in Benedict's
solution, forming a red precipitate of copper(I) oxide.
 PHYSIC AL PROPERTIES

SolubilityMonosaccharides are highly soluble in water

due to their multiple hydroxyl groups, which form hydrogen
bonds with water molecules.
Crystalline Nature: Monosaccharides typically crystallize
into solid forms. For example, glucose can crystallize into
different forms, such as alpha-glucose and beta-glucose.
Optical Activity: Monosaccharides are optically active due
to the presence of one or more chiral centers.They can
rotate plane-polarized light, with D- and L- forms based on
their configuration relative to glyceraldehyde.
 BIOLAGICAL PROPERTIES

• Energy Source: Monosaccharides like glucose are primary

energy sources for cells.They are metabolized via
glycolysis
and other pathways to produce ATP.
• Building Blocks: Monosaccharides serve as building blocks
for larger carbohydrates, including disaccharides,
oligosaccharides, and polysaccharides.
• Signaling and Recognition: Monosaccharides and their
derivatives play critical roles in cell signaling, recognition,
and adhesion processes. For example, glycoproteins and
glycolipids on cell surfaces are involved in immune
responses and cell communication.
 ANALYTICAL TECHNIQUES

• Chromatography: Techniques like HPLC and GC for

• separating and identifying monosaccharides.
• Mass Spectrometry (MS): For molecular identification
• and structural analysis.
• NMR Spectroscopy: For detailed structural information.
• Electrophoresis: For separating monosaccharides based
• on size and charge.
 EX AMPLES OF SOME
MONOSACC HARIDES

• Glucose (C6H12O6):The primary energy source in cells.

• Fructose (C6H12O6): Found in fruits; a ketohexose.
• Galactose (C6H12O6): Part of lactose; an aldohexose.
 FORENSIC RELEVANCE

The detection of glucose and other

sugars can be critical in cases of diabetes-related deaths or
in postmortem biochemistry to determine the physiological
state before death.
 FUNCTIONS OF MONOSAC ARIDES

• ● Glucose is an important source of energy in humans and

plants. Plants store
• the excess glucose as starch which humans and herbivores
consume.
• ● The presence of galactose is in milk sugar (lactose), and
fructose in fruits and
• honey makes these foods sweet.
• ● Ribose is a structural element of nucleic acids and some
coenzymes.
• ● Mannose is a constituent of mucoproteins and glycoproteins
required for the
• proper functioning of the body.
ISOMERISM
Isomers are defined as molecules with the same chemical formula, but
have different structural formulae.
Isomerism can be of two types: Structural isomerism and Stereoisomerism.

1.Structural Isomerism:
(A) Chain Isomerism:
Occurs when the carbon skeleton
of the molecule can be rearranged.
Eg: glucose and fructose.
Both having formula C6H12​O6.
2. Stereoisomerism:
((A) Enantiomers:
Non-superimposable mirror
images of each other.
Monosaccharides often
exhibit enantiomerism due to
the presence of chiral centres
(asymmetric carbon atoms).
Eg : D-glucose and L-glucose.
(B) Diastereomers:
These are stereoisomers that
are not mirror images of each
other.
Eg : D-glucose and D-
galactose are diastereomers.
They differ in the arrangement
of groups around one or more
chiral centres but are not
mirror images.
(C) Epimers:
A subtype of diastereomers
that differ in configuration at
only one specific carbon atom.
D-glucose and D-mannose are
epimers differing only at the
C-2 position.
(D) Anomers:
Isomers that differ at the anomeric carbon.
Eg : α-D-glucose and β-D-glucose.
α- glucose and β- glucose differ only in the configuration of
hydroxyl group (-OH) at anomeric carbon.
The six-membered cyclic structure of glucose is called pyranose
structure.
Pyranose structure of glucose: The six membered ring contains an
oxygen atom because of its resemblance with pyran is called
pyranose form.
3. Conformational Isomerism:
This type of isomerism arises due to the different spatial orientations
of the atoms that can be adopted by rotating around single bonds.
Eg : the chair and boat forms of glucose are conformational isomers.
The chair form is more stable and less strained conformation.
4. Tautomers:
Isomers that can
interconvert by a chemical
reaction, typically
involving the shift of a
hydrogen atom and a
double bond.
Eg : D-glucose can
tautomerize to D-fructose
under certain conditions,
involving a shift from an
aldehyde form to a ketone
form through an ene-diol
intermediate.
SUGAR DERIVATIVES
Sugar derivatives of monosaccharides are modified forms of simple
sugars (monosaccharides) where the chemical structure is altered
through the addition, substitution, or removal of certain functional
groups.
Here are some common sugar derivatives of monosaccharides:

1.Sugar Alcohols (Alditols):

Sorbitol: Derived from glucose.
Mannitol: Derived from mannose.
Xylitol: Derived from xylose.
Erythritol: Derived from erythrose.
Sorbitol can be synthesized Mannitol is the product of the
through catalytic hydrogenation of reaction of the reaction mannose
d-glucose to form d-sorbitol. with a reducing agent
𝑁𝑎𝐵𝐻4 𝑜𝑟 𝐻2/𝑃𝑑 can be used as (e.g. NaBH4/H3O+; H2/Ni; Na-Hg)
reagent.
 Reduction of
D-xylose to xylitol
by Xylose
Reductase (XR)

Erythritol was shown to be

an excellent HO• radical
scavenger. The reaction of
erythritol with hydroxyl
radicals resulted in the
formation of erythrose and
erythrulose by abstraction
of a carbon-bound
hydrogen atom.
2.Sugar Acids:
Aldonic Acids: Formed by the oxidation of the aldehyde group of
aldoses to a carboxylic acid. Example: Gluconic acid (from glucose).
Uronic Acids: Formed by the oxidation of the terminal primary alcohol
group of aldoses to a carboxylic acid. Example: Glucuronic acid (from
glucose).
Aldaric Acids: Formed by the oxidation of both the aldehyde group and
the terminal primary alcohol group to carboxylic acids. Example:
Glucaric acid (from glucose).

Gluconic acid is produced by

oxidizing glucose in the presence of
bromine water.
Two-steps synthesis of D-glucaric acid via D-gluconic acid
by electrocatalytic oxidation of D-glucose on gold electrode
3. Amino Sugars:
Glucosamine: Derived from glucose, where the hydroxyl group on
carbon 2 is replaced by an amino group.
Galactosamine: Derived from galactose, where the hydroxyl group on
carbon 2 is replaced by an amino group.
4. Deoxy Sugars:
Deoxyribose: A component of DNA, derived from ribose by removing
an oxygen atom from carbon 2.
Fucose (C6H12O5): A deoxyhexose sugar often found in
glycoconjugates.

Fucose
5. Phosphorylated Sugars:
Glucose-6-phosphate: A phosphorylated derivative of glucose,
important in glycolysis.
Fructose-1,6-bisphosphate: A phosphorylated derivative of
fructose, also significant in glycolysis.
6. Glycosides:
Formed by the reaction of a sugar with another molecule,
typically an alcohol or another sugar, leading to a glycosidic
bond.
Eg : Maltose (formed from two glucose molecules).
7. N-Acetyl Sugars:
N-Acetylglucosamine (GlcNAc, C8H15NO6): Formed by adding an
acetyl group to the amino sugar glucosamine.
N-Acetylmuramic Acid (NAM, C11H19NO8): A component of
bacterial cell walls, derived from GlcNAc.
These derivatives play critical roles in various biological processes, including
energy metabolism, structural functions in cells, and signaling.

N-Acetylglucosamine
DISACCHARIDES
A disaccharide (also called a double sugar ) is the sugar formed when two
monosaccharides (simple sugars) are joined by glycosidic linkage.
Like monosaccharides, disaccharides are soluble in water.
Three common examples are sucrose, lactose, and maltose.
Disaccharides are those carbohydrates that on hydrolysis with acids or
enzymes give two molecules of monosaccharides which can either be the same
or different.
The oxide linkage is formed after the loss of the water molecule and then the
two monosaccharides are formed by that linkage. When two monosaccharide
units are joined via the oxygen atom then that linkage is called a glycosidic
linkage.
STRUCTURE OF DISACCHARIDES
(SUCROSE)
The most common disaccharide is sucrose which gives D -(+)- glucose and D-
(-)- fructose on hydrolysis.
Both the monosaccharides i.e. glucose and fructose are connected through the
glycosidic linkage between alpha glucose and second carbon beta fructose.
Sucrose is a non-reducing sugar as both the reducing groups of glucose and
fructose are involved in the glycosidic bond formation.
EXAMPLES OF DISACCHARIDES
1. SUCROSE
Sucrose being dextrorotatory in nature
gives dextrorotatory glucose as well as
levorotatory fructose on hydrolysis.
The overall mixture is levorotatory and
this is because the levorotation of
fructose (-92.4) is more than the
dextrorotation of glucose (+52.5).
2. MALTOSE
Maltose is also one of the disaccharides
which have two α -D-glucose units
which are connected by the first carbon
of the glucose and also linked to the
fourth carbon of another glucose unit.
In the solution, a free aldehyde can be
produced at the first carbon of the
second glucose of the solution and it is
a reducing sugar as it shows reducing
properties.
3. LACTOSE

Commonly it is called milk sugar as

this disaccharide is found in milk.
It is made up of Beta-D-galactose and
β-D-glucose.
The bond is between the first carbon of
galactose and the fourth carbon of
glucose.
This is also a reducing sugar.
POLYSACCHARIDES
Polysaccharides are major classes of biomolecules.
They are long chains of carbohydrate molecules, composed of several smaller
monosaccharides.
These complex bio-macromolecules function as an important source of
energy in animal cells and form a structural component of a plant cell.
It can be a homopolysaccharide or a heteropolysaccharide depending upon
the type of the monosaccharides.
Polysaccharides can be a straight chain of monosaccharides known as linear
polysaccharides, or it can be branched known as a branched polysaccharide.
CHARACTERISTICS OF
POLYSACCHARIDES
Polysaccharides have the following properties:
They are not sweet in taste.
Many are insoluble in water.
They are hydrophobic in nature.
They do not form crystals on desiccation.
Can be extracted to form a white powder.
They are high molecular weight carbohydrates.
Inside the cells, they are compact and osmotically inactive.
They consist of hydrogen, carbon, and oxygen. The hydrogen to oxygen ratio
is 2:1
 TYPES OF POLYSACCHARIDES
Polysaccharides are categorized into two types:

A) Homopolysaccharides :

A polysaccharide that contains the same type of monosaccharides is known as

a homopolysaccharide.
Some of the important homopolysaccharides are:
1. Glycogen
2. Cellulose
3. Starch
4. Inulin
B) Heteropolysaccharides :

A polysaccharide that contains different types of monosaccharides is known

as heteropolysaccharide.
Some of the important heteropolysaccharides are:
1. Hyaluronic Acid
2. Heparin
3. Chondroitin-4-sulfate
4. Gamma globulin
 FUNCTIONS OF POLYSACCHARIDES
The polysaccharides serve as a structural organization in animals and
plants.
Other functions of polysaccharides include:

1. They store energy in organisms.

2. Due to the presence of multiple hydrogen bonds, the water cannot invade the
molecules making them hydrophobic.
3. They allow for changes in the concentration gradient which influences the
uptake of nutrients and water by the cells.
4. Many polysaccharides become covalently bonded with lipids and proteins
to form glycolipids and glycoproteins. These glycolipids and glycoproteins
are used to send messages or signals between and within the cells.
5. They provide support to the cells. The cell wall of plants is made up of
polysaccharide cellulose, which provides support to the cell wall of the
plant. In insects and fungi, chitin plays an important role in providing
support to the extracellular matrix around the cells.
CONCLUSION
Carbohydrates are one of the four major essential biomolecules required by
living organisms.
Organisms consume them in several forms, and they are classified into four
groups based on the number of monomer units their structure has.
They include monosaccharides, disaccharides, oligosaccharides, and
polysaccharides.
All carbohydrates contain molecules like glucose, fructose, cellulose,
starch, glycoproteins, and chitin which are involved in several organismal
functions. Their functions range from providing energy to the cells,
supporting the structural integrity of cells, to supporting the organism’s
growth and development.
 REFERENCES
BOOKS
Cell biology biochemistry - Prof. K. K.Bhaskaran & Prof. A. R.Ajith Kumar
Ramesh
LINKS
https://epgp.inflibnet.ac.in/
https://theory.labster.com/isomers/
https://byjus.com/
THANK YOU