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Carbohydrates

Carbohydrates are one if the 4 most impt classes of biological molecules that make up the bodies of all living organisms

Carbohydrates, proteins, lipids and nucleic acids account for over 90% of total dry mass of the cell

These four most impt classes of biological molecules are organic (contains Carbon, Hydrogen and Oxygen)

Insoluble carbohydrate polymers serve as structural and protective elements in cell walls and connective tissues of animals

Other carbohydrate polymers lubricate skeletal joints and participate in the recognition and adhesion between cells

More complex carbohydrate polymers covalently attach to proteins or lipids (Glycoproteins / Glycolipids) and involved in
receiving signals from external surroundings

The unique feature of carbon atom

Small atom, low in mass

Each carbon is able to form 4 strong and stale covalent bonds with a variety of other atoms like hydrogen, oxygen, nitrogen,
phosphorous and sulfur

There is a tetrahedral arrangement when a carbon atom is bond to 4 other atoms

Carbon has the unusual ability to bond with itself, forming carbon-carbon bonds, thus building up large carbon skeletons with
ring and/or chain structures

Classes of Carbohydrates

Carbohydrates are hydrates of carbon and hence have a general formula of Cx(H2O)y

They are made up of units containing carbon, hydrogen and oxygen atoms in the ratio of 1:2:1

There are 3 main classes of carbohydrates


-Monosaccharides
-Disaccharides
-Polysaccharides

Monosaccharides

A monosaccharide is a carbohydrate that cannot be hydrolysed to simpler carbohydrates

They are classified according to the number of carbon atoms in the molecule

Number of C atoms Name Examples


3C Triose Glyceraldehyde
4C Tetrose Threose
5C Pentose Ribose, Ribulose
6C Hexose Glucose, Galactose, Fructose
7C Heptose Sedoheptulose

Of these, 5C and 6 C are the most common


Structure of Monosaccharides

General formula of (CH20)n where n>3

Monosaccharides show isomerism

Glucose and Fructose are Structural isomers (a big difference in structure)

Glucose and Galactose are stereoisomers (one portion of the chain is mirrored)

There are 3 types of isomers of monosaccharides

-Aldose and Ketose


-Open-chain form and ring form
-alpha isomer and beta-isomer

Aldose and Ketose

Aldose has an aldehyde functional group

Ketose has a keto group

Open-chain form and ring form

Linear form is rare due to its instability

Almost all glucose molecules in a solution spontaneously react to form one of the two ring structures, the alpha and beta
forms of glucose

Both alpha and beta forms exist in equilibrium, but beta forms more commonly as it is slightly more stable than the alpha
form

The ring form of monosaccharides are used to make disaccharides and polysaccharides

In glucose, C1 combines with the oxygen atom on C5 to form a 6-sided structure known as a pyranose ring

In the case of fructose, C2 links to the oxygen atom in C5 rather than C1 to form a 5-sided structure known as a furanose ring

Alpha-isomer and beta-isomer

Glucose can exist in 2 possible ring forms

The -OH on C1 can project below the plane of the ring (with C6 on the top) to form alpha-glucose, or it can be prosecuted
above the plane of the ring (same plane as C6) to form a beta-glucose

A glucose molecule in solution can switch spontaneously from the open-chain form to either of the two ring forms and back
again

Alpha and beta glucose have similar properties, however, the relatively small difference in the structure explains why storage
polysaccharides like starch and glycogen are made up of alpha-glucose while structural polysaccharides like cellose are made
up of beta-glucose

Properties of Monosaccharides

Physical:
-Small
-Low Mr
-sweet
-Crystalline in appearance
-Readily soluble in water (polar), hence exerts osmotic pressure

Chemical:
-All monosaccharides are reducing sugars
-Monosaccharides can be oxidized by relatively mild oxidizing agents like Cu2+ present in Benedict’s solution
-The carbonyl carbon is oxidized t a carboxyl group. Sugars capable of reducing ferric Cu2+ are called reducing sugars

-All carbohydrates are the source of energy or plants and animals, but monosaccharides can act as respiratory substrates
-Monosaccharides are raw materials for synthesis of other carbohydrates like polysaccharides, proteins, lipids, nucleic acids
and coenzymes
-In plant cells, the osmotic pressure monosaccharides exert accounts for the turgidity of plant cells, elongation of young plant
cells and transportation of water from cell to cell and opening and closing of the stomata

Disaccharides

A disaccharide is made by joining two monosaccharides

Examples are maltose, lactose and sucrose

Disaccharides are formed by glycosidic linkages

General formula of disaccharides: C12H22O11

Formation of disaccharides from two monosaccharides is a condensation reaction

Glycosidic bonds are usually formed between C1 and C4, hence the bond name would be ,4 glycosidic bond

This reaction is reversible through the process of hydrolysis

Properties of disaccharides

Physical:
-Small
-Low Mr
-Sweet
Crystalline in appearance
-Polar, thus exert osmotic pressure

Chemical:
-Some disaccharides are reducing (maltose and lactose) while others aren’t (sucrose)
-Disaccharides can be hydrolysed into monosaccharides by:
-incubating it with a dilute acid at 100*C
-incubating it with an enzyme at room temp

Functions of Disaccharides

Disaccharides have the same functions as monosaccharides (respiratory substrates, raw materials for synthesis)since the
latter are produced when disaccharides are hydrolysed

Disaccharides are also osmotically active substances and thus have the same osmotic functions as that of monosaccharides

Disaccharide Composition Functions


Maltose Glucose + Glucose Respiratory substrate
Production of starch digestion by
amylase
Lactose Glucose + Galactose Respiratory substrate
Found exclusively in milk
Impt carbohydrate source for young
mammals
Sucrose Glucose + Fructose Respiratory substrate
Chief form of transported sugars in
plants due to high solubility (Sugars
largely stored as starch)
Storage in some plants (onion)

Polysaccharides

A polysaccharide is a polymer whose constituent monomers (usually hexoses) are monosaccharides

Example, starch, glycogen, cellulose

General formula of (C6H10O5)n where n = number of hexose units linked together in a polysaccharide

A polysaccharide consists of many repeating units of monosaccharides joined together by glycosidic bonds, forming long
straight chains (in cellulose), helical chains (in amylose), or branched chains (in amylopectin)

If 1,4 glycosidic bonds and 1,6 glycosidic bonds are formed between 2 alpha isomers, then they are called alpha(1→4)
glycosidic bond/linkage and alpha(1→6) glycosidic bond/linkage respectively

Properties of Polysaccharides

Physical:
-Not sweet
-Not crystalline in appearance
-Insoluble in water, thus does not exert osmotic pressure

Chemical:
-Non-reducing
-Can be hydrolysed to disaccharides and monosaccharides by concentrated acids and in the presence of amylase
Functions of Polysaccharides

Based on functions, polysaccharides can be divided into 2 groups, Storage polysaccharides ad Structural polysaccharides

Storage polysaccharides function mainly as food and energy stores, while structural polysaccharides are used to make certain
structural materials of cells

Starch: Storage Polysaccharides in Plants

Main storage polysaccharide in plant (absent in animals)

Consist of two components - amylose and amylopectin, both of which are made up of many alpha-glucose units

A suspension of amylose in water gives a blue-black colour with iodine-potassium iodide solution, whereas that of
amylopectin gives a red-violet colour (this forms the basis for the test of starch)

Amylose:

It is an unbranched polymer of several hundreds to few thousands of alpha-glucose linked together by alpha(1→4) glycosidic
bonds, which cause the amylose chain to coil helically into more compact shape

For every complete turn of the helix, there are 6 alpha-glucoses units

Helix is held together by hydrogen bonds formed between -OH groups

Since most of the -OH groups of the alpha-glucose units project into the interior of the helix, cross-linking of amylose chains
is not possible

Amylose is not polar, unless the temp is high enough to overcome the hydrogen bonds holding the helix together

Amylopectin:

It is a branched polymer of alpha-glucose units whose number is more than twice of that in amylose

The alpha-glucose units in the main chain are linked by alpha(1→4) glycosidic bonds, while the side chains are attached to
the main chain by alpha(1→6) glycosidic bonds

Branching decreases the ability of the chains to bind together with one another and increases the binding of water molecules
to the chains, amylopectin is more soluble than thee unbranched amylose in water

Both components of starch form a complex 3D structure where the amylose helices are entangled in the branches of the
amylopectin molecules

Structure of Amylopectin

In plants, it is packed into spherical plastids called starch grains, which occur particularly in chloroplasts of plant cells or in
specialized structures such as seeds or potato tubers

2 ways to hydrolyse starch back to glucose:


-chemical method: incubate starch with dilute acid @ 100*C
-enzymatic method: incubate starch with enzymes at room temp

Glycogen: A highly branched storage polysaccharide in animals

Animal equivalent of starch


Found in liver and skeletal muscles of vertebrae animals and many fungi

Glycogen is the most branched out of the 3, so it is also the most soluble

Cellulose: A structural Polysaccharide in Plants

Most abundant organic molecule on earth (abt 50% of carbon found in plants is in cellulose)

Structural component of ALL cell walls

Polymer of about 10,000 beta-glucose units linked by beta(1→4) glycosidic bonds, forming unbranched, linear chain rather
than a helix chain, as the glycosidic bonds occur alternatively on opposite ends

H-bonds may form between the protruding -OH groups on adjacent cellulose chains, resulting in rigid cross-linking between
chains

Cross-link chains associate in groups to form micelles, which are arranged in larger bundles to form micro fibrils, which
combine to form macro fibrils, which are of great tensile strength

The tensile strength provides the support and mechanical strength to plant cells and prevent them from bursting when placed
in hypotonic solutions

There are large spaces between the cellulose macro fibrils to allow water and solute molecules to pass through the cell walls