Definition and function, Classification, Isomerism of monosaccharide, Properties of monosaccharide,

Structure and functions of modified monosaccharide, disaccharides, oligosaccharides, polysaccharides and

Definition
Carbohydrates are indeed the most abundant organic molecules found in nature and play crucial roles in
various biological processes. They are generally characterized by their composition of carbon (C), hydrogen
(H), and oxygen (O), often in the ratio that resembles the empirical formula (C.H2O)n. where n is 3 or more.
This formula suggests that carbohydrates can be thought of as "hydrates of carbon," where one carbon
atom is associated with one water molecule.
However, as you mentioned, this definition has its limitations. Certain compounds, such as acetic acid
(C₂H₄O₂) and lactic acid (C₃H₆O₃), fit the structural formula of carbohydrates yet do not function as
carbohydrates because they lack the polyhydroxy structure or do not produce aldehydes or ketones upon
hydrolysis.
Moreover, there are true carbohydrates, like rhamnohexose (C₆H₁₂O₅) and deoxyribose (C₅H₁₀O₄), that do
not adhere strictly to the (C.H₂O)n formula. This complexity indicates that while the general formula is
helpful, it is not sufficient to categorize all compounds as carbohydrates.
In a more precise definition, carbohydrates can be classified as polyhydroxy aldehydes or ketones. They
can also be broken down into simpler sugars, known as monosaccharides, and more complex forms like
disaccharides, oligosaccharides, and polysaccharides. The term "sugar" typically refers to the simpler
carbohydrates that are sweet-tasting and soluble in water, such as glucose and fructose.
So, Carbohydrates are organic compounds consisting of carbon, hydrogen, and oxygen, typically with a
hydrogen-to-oxygen ratio of 2:1, similar to water (hence the name "carbohydrate," derived from "carbon"
and "hydrates"). They serve as a major source of energy for the body and are found in a variety of foods,
including grains, fruits, vegetables, and dairy products.
Function
1. Energy Source: Carbohydrates are a major source of energy for the body. Upon digestion, they are
broken down into glucose, which is used by cells for energy. This is particularly essential for high-
energy activities and for organs like the brain, which relies heavily on glucose.
2. Energy Storage: Carbohydrates are stored in the body as glycogen in the liver and muscles.
Glycogen can be converted back into glucose when the body needs a quick source of energy.
3. Structural Components: Certain carbohydrates play structural roles in organisms. For instance,
cellulose, a polysaccharide, is a key component of the cell wall in plants, providing rigidity and
support.
4. Cell Recognition and Signaling: Carbohydrates are involved in cell recognition and communication.
Glycoproteins and glycolipids, which have carbohydrate moieties, are crucial for cell signaling,
adhesion, and recognition processes.
5. Metabolic Precursors: Carbohydrates can serve as precursors for the biosynthesis of various
biomolecules. For example, ribose and deoxyribose are carbohydrates that form part of the
structure of RNA and DNA, respectively. Carbohydrates are precursors for many organic compounds
(fats, amino acids).
6. Regulation of Blood Sugar Levels: The intake and digestion of carbohydrates help regulate blood
sugar levels. The body uses insulin and glucagon to manage glucose levels, maintaining
homeostasis.
7. Fiber: Some carbohydrates, particularly dietary fiber, are not digestible but play a crucial role in
digestive health. Fiber aids in bowel regularity, helps manage blood sugar levels, and can contribute
to cardiovascular health.
8. Flavor and Texture: In food, carbohydrates contribute to flavor and texture, enhancing the
palatability and enjoyment of various foods.
Classification
Carbohydrates can be classified into several categories based on their structure, size, and complexity. The
main classifications are:
1. Based on Structure:
 Monosaccharides: These are the simplest form of carbohydrates, consisting of single sugar units.
Examples include glucose, fructose, and galactose.
 Disaccharides: These are formed by the combination of two monosaccharides through a glycosidic
bond. Examples include sucrose (glucose + fructose), lactose (glucose + galactose), and maltose
(glucose + glucose).
 Oligosaccharides: These consist of 3 to 10 monosaccharides. Common examples are raffinose and
stachyose, which are often found in beans and other vegetables.
 Polysaccharides: These are large molecules made up of long chains of monosaccharides. They are
typically used for energy storage or structural purposes. Examples include starch, glycogen, and
cellulose.
2. Based on Function:
 Storage Carbohydrates: These provide energy reserves. Examples include starch in plants and
glycogen in animals.
 Structural Carbohydrates: These provide structural support. Examples include cellulose in plant cell
walls and chitin in the exoskeletons of arthropods.
3. Based on Solubility:
 Soluble Fiber: This type dissolves in water and can help lower blood cholesterol levels. Examples
include pectin and some gums.
 Insoluble Fiber: This type does not dissolve in water and aids in digestive health. Examples include
cellulose and lignin.
4. Based on the Number of Sugar Units:
 Trioses: Three carbon sugars (e.g., glyceraldehyde).
 Tetroses: Four carbon sugars (e.g., erythrose).
 Pentoses: Five carbon sugars (e.g., ribose).
 Hexoses: Six carbon sugars (e.g., glucose).
 Heptoses: Seven carbon sugars (less common, e.g., sedoheptulose).
5. Based on Chemical Behavior:
 Reducing Sugars: Carbohydrates that can donate electrons to other molecules (e.g., glucose and
fructose).
 Non-reducing Sugars: Carbohydrates that cannot act as reducing agents (e.g., sucrose).

Isomerism in monosaccharides:
Isomerism in monosaccharides is a fascinating topic in carbohydrate chemistry, primarily due to the
presence of chiral centers and the structural variability of these molecules. Here are some key points
regarding the basis of isomerism in monosaccharides:
1. Chiral Carbon Atoms:
 Chirality: A carbon atom is considered chiral if it is attached to four different groups. In
monosaccharides, chiral carbons are crucial because they give rise to stereoisomers.
 Stereogenic Centers: The number of chiral centers in a sugar molecule determines how many
stereoisomers (i.e., possible configurations) it can have.
2. Number of Isomers:
 The formula to determine the maximum number of stereoisomers for a sugar with n chiral centers
is 2n.
 o For example, a monosaccharide with 3 chiral centers would have 23=8 possible
stereoisomers.

Isomerism in monosaccharides refers to the phenomenon wherein two or more compounds have the same
chemical formula but different structural or spatial arrangements. There are several types of isomerism
that can be observed in monosaccharides:
1. Structural Isomerism (Constitutional Isomerism): This type of isomerism occurs when the atoms in
a molecule are connected in different ways. In monosaccharides, this can manifest in several ways:
o Aldose vs. Ketose: Monosaccharides can either have an aldehyde group (-CHO) or a ketone
group (C=O). For example, glucose is an aldose, while fructose is a ketose.
o Chain Isomerism: This occurs when monosaccharides differ in the arrangement of carbon
atoms. For instance, D-glucose and D-mannose are both C6H12O6 but have different
structural arrangements.
2. Stereoisomerism: This type of isomerism occurs when compounds have the same structure but
differ in the spatial arrangement of atoms. For monosaccharides, this can include:
o Geometric Isomerism: While less common in monosaccharides, some cyclic forms can
exhibit geometric isomerism.
o Enantiomerism: This refers to a type of stereoisomerism where two isomers are non-
superimposable mirror images of each other. For example, D-glucose and L-glucose are
enantiomers.
o Diastereoisomerism: This occurs in monosaccharides that have two or more chiral centers.
For instance, D-glucose and D-mannose are diastereomers since they differ in configuration
at one of the chiral centers.
3. Anomeric Isomerism: This type of stereoisomerism is specific to cyclic forms of monosaccharides. It
occurs at the anomeric carbon (the carbon derived from the carbonyl carbon during cyclization).
For example, in D-glucose, the cyclic form can exist as α\alphaα-D-glucose (with the -OH on the
anomeric carbon pointing down) or β\betaβ-D-glucose (with the -OH pointing up).

Enantiomers:
 These are a pair of molecules that are non-superimposable mirror images of each other. Think of
your left and right hands—they're mirror images but can't perfectly overlap.
 Enantiomers have identical physical properties (like boiling point) but differ in the way they
rotate plane-polarized light and how they interact with other chiral molecules.
 Example: D-glucose and L-glucose.
Diastereomers:
 These are stereoisomers (molecules with the same molecular formula and bonding sequence)
that are not mirror images of each other.
 They have different physical and chemical properties, unlike enantiomers.
 Example: Cis-trans isomers in alkenes, or D-threose and D-erythrose.
Epimers:
 A special type of diastereomer, where the two molecules differ in configuration at only one
specific carbon atom out of several chiral centers.
 Example: D-glucose and D-mannose differ only at the C2 carbon.
Anomers:
 Another subtype of diastereomers, but specific to cyclic molecules, like sugars.
 Anomers differ at the anomeric carbon—the carbon derived from the carbonyl group during
cyclization (C1 in glucose, for example).
 Example: α-D-glucose and β-D-glucose differ in the orientation of the -OH group at the anomeric
carbon.

 Optical Activity of Sugars: Sugars are optically active due to the presence of chiral carbon atoms.
When plane-polarized light passes through a sugar solution, the light's plane is rotated. Sugars can be
classified as dextrorotatory (rotate light to the right, denoted as "+") or levorotatory (rotate light to the
left, denoted as "−"). The degree of rotation depends on the sugar's concentration, the length of the
polarimeter tube, and the specific sugar molecule.
 Mutarotation: This is the change in the optical rotation of a sugar solution over time due to the
interconversion between its α- and β-anomers in aqueous solutions. For example, in D-glucose, the α-
anomer has a specific rotation of +112°, and the β-anomer has +19°. When dissolved, they reach an
equilibrium mixture with a specific rotation of +52.5°. This phenomenon occurs because of the ring-chain
tautomerism of sugars.
 Racemic Mixture: A racemic mixture contains equal amounts of two enantiomers (mirror-image
isomers) of a chiral molecule. Such mixtures are optically inactive because the rotations caused by the
two enantiomers cancel each other out. For example, a racemic mixture of lactic acid would have no net
optical rotation.
Structure of Monosaccharides Monosaccharides are the
Monosaccharides are simplest carbohydrates and
carbohydrates with the general serve as the fundamental
formula (CH₂O)ₙ. Here are some building blocks for more complex
details: carbohydrates like disaccharides
and polysaccharides. Key
Open Chain Form: Contains a characteristics include:
carbon chain with one carbonyl 1. Basic Structure:
group (C=O) and multiple Composed of carbon (C),
hydroxyl groups (-OH). hydrogen (H), and oxygen
(O) in the formula
Aldoses: Contain an aldehyde (CH₂O)ₙ, with common
group (-CHO), e.g., Glucose. examples like glucose,
fructose, and galactose.
Ketoses: Contain a keto group (- 2. Classification: They can
CO-), e.g., Fructose. be classified by carbon
count (triose, tetrose,
Cyclic Form: In aqueous pentose, hexose) and by
solutions, monosaccharides functional groups
often exist in a ring form due to (aldoses like glucose and
the reaction between the ketoses like fructose).
carbonyl group and a hydroxyl 3. Stereochemistry: They
group. can possess multiple
chiral centers, leading to
Furanose: 5-membered ring. D- and L- stereoisomers.
4. Solubility: Generally
Pyranose: 6-membered ring. water-soluble due to
hydroxyl groups forming
Below is a basic structure for hydrogen bonds.
glucose: 5. Sweetness: Many, such
as glucose and fructose,
Fischer Projection (Open Chain are sweet and important
Form): in food.
6. Reactivity: Can undergo
CHO oxidation, reduction, and
| glycosylation reactions.
H-C-OH Notable reactions include:
|  Reduction: Converts
HO-C-H monosaccharides to sugar
| alcohols (e.g., glucose to
H-C-OH sorbitol).
|  Oxidation: Converts them
H-C-OH to acids (e.g., glucose to
| gluconic acid).
CH₂OH  Benedict's Test: Reduces
Haworth Projection (Cyclic Form copper(II) ions to a
- β-D-Glucopyranose): reddish precipitate in
certain conditions.
O  Formation of
/\ Disaccharides: Two
H-C-OH | monosaccharides
| | condense to form
HO-C-H | disaccharides, like
| | glucose and fructose
H-C-OH forming sucrose.
|
CH₂OH
Important Reactions of
Monosaccharides
Reduction:

The carbonyl group in aldoses

Example: Glucose → Sorbitol.

Oxidation:

The aldehyde group is oxidized to

Example: Glucose → Gluconic

Glycosidic Bond Formation:

Two monosaccharides combine

Example: Glucose + Fructose →

Benedict’s Test:

Reducing sugars reduce

Used to identify reducing sugars

Fermentation:

Monosaccharides are converted

Example: Glucose → Ethanol +

Mutarotation:
In aqueous solution,
monosaccharides alternate
between α and β anomers due to
the opening and closing of the
ring structure.

Example: α-D-Glucose ⇌ Open

Formation of Derivatives:

Monosaccharides form
derivatives like amino sugars or
deoxy sugars.

Example: Glucose → N-
Acetylglucosamine.