1.

CARBOHYDRATES

General Information:
Carbohydrates are the most abundant class of organic compounds found in living organisms. They originate as products of photosynthesis, an endothermic reductive condensation of carbon dioxide requiring light energy and the pigment chlorophyll.

n H2O + CO2 + Energy

CnH2nOn + n O2

General Information:
The formulas of many carbohydrates can be written as carbon hydrates, Cn(H2O)n, hence their name. The carbohydrates are a major source of metabolic energy, both for plants and for animals that depend on plants for food. Aside from the sugars and starches that meet this vital nutritional role, carbohydrates also serve as a structural material (cellulose), a component of the energy transport compound ATP, and one of three essential components of DNA and RNA. Carbohydrates are called saccharides or, if they are relatively small, sugars.

A- Simple Sugars
Contain the elements carbon, hydrogen, and oxygen. The name carbohydrate literally means water compounds of carbon. The general formula for simple sugars is Cn(H2O)n. This class of compounds is better described as Polyhydroxy aldehydes and ketones. The simplest carbohydrates are glyceraldehyde and dihydroxyacetone.
O HC C HO H CH2OH O HOH2C C CH2OH

glyceraldehyde

dihydroxyacetone

A - Methods of Classification:
Several methods are used to classify carbohydrates. 1-One method of classification is based on whether the carbohydrate can be broken down into smaller units. Monosaccharides cannot be broken down into smaller units by hydrolysis. Sometimes called simple sugars. Disaccharides can be broken down (hydrolyzed) into two monosaccharide units. Oligosaccharides can be broken into three to six monosaccharide units. Polysaccharides composed of 7 or more mono-saccharide units.

A - Methods of Classification:
Several methods are used to classify carbohydrates.

2-Another method is based on the number of carbons found in a simple sugar.

If it has 3 carbons it is called a triose. If it has 4 carbons it is called a tetrose. If it has 5 carbons it is called a pentose. If it has 6 carbons it is called a hexose.

A - Methods of Classification:
Several methods are used to classify carbohydrates. 3-Another method uses the kind of carbonyl group. A- Aldose: A monosaccharide with an aldehyde group.
O HC H H C C OH OH

CH2OH erythrose

A - Methods of Classification:
Several methods are used to classify carbohydrates.

3-Another method uses the kind of carbonyl group. B- Ketose A monosaccharide with a ketone group..
CH2OH C O HO C H H C OH H C OH CH2OH fructose

Usually combine the carbonyl classification and the number classification together.
H C H H C H C OH HO O H H C C C C OH H OH OH HO H H O CH2OH C C C C O H OH OH

CH2OH glyceraldehyde aldotriose

CH2OH glucose aldohexose

CH2OH fructose ketohexose

B- Stereoconfigurations of simple sugars.

Carbohydrates contain many stereocenters. 1- If the OH group is found on the right side of the carbon chain, the sugar is designated as a D sugar. 2- If the OH group is found on the left side of the chain of carbons, the sugar is designated as an L sugar.
H H C C O OH H HO C C O H

CH2OH D-glyceraldehyde D-aldotriose

CH2OH L-glyceraldehyde L-aldotriose

B- Stereoconfigurations of simple sugars.

CHO H C OH CH2OH D-glyceraldehyde CHO H H C OH C OH CH2OH D-erythrose CHO HO C H H H C OH C OH CH2OH D-arabinose CHO HO C H HO C H H H C OH C OH CH2OH D-mannose H H H CHO C OH C OH C OH CH2OH D-glucose HO C H H H CHO HO C H C OH C OH CH2OH D-altrose H C OH H H H CHO H C OH H H C OH C OH CH2OH D-ribose CHO C OH C OH C OH CH2OH D-allose CHO HO C H HO C H H C OH CH2OH D-lyxose CHO HO C H HO C H HO C H H C OH CH2OH D-tallose H CHO C OH HO C H HO C H H C OH CH2OH D-galactose H H HO C H C OH C OH CH2OH D-idose HO C H H H H CHO HO C H C OH CH2OH D-threose CHO C OH C OH CH2OH D-xylose CHO H H H CHO C OH C OH C OH CH2OH D-gulose HO C H

H C OH

HO C H

B- Stereoconfigurations of simple sugars.

CH2OH C O CH2OH dihydroxyacetone

CH2OH C H C O OH

CH2OH D-erythrulose CH2OH C HO H C C O H OH H H

CH2OH C C C O OH OH

CH2OH D-xylulose

CH2OH D-ribulose

CH2OH C HO HO H C C C O H H OH H HO H

CH2OH C C C C O OH H OH HO H H

CH2OH C C C C O H OH OH H H H

CH2OH C C C C O OH OH OH

CH2OH D-tagatose

CH2OH D-sorbose

CH2OH D-fructose

CH2OH D-psicose

Cyclic Structures:
Five membered sugar rings are known as furanose rings.
H C O HO CH2 H H OH OH O H OH H HO CH2 + H OH OH H O H H OH

H C OH H C OH H C OH CH2OH D-ribose

-D-ribofuranose

-D-ribofuranose

Cyclic Structures: Six membered sugar rings are known as

pyranose rings.
H H H H C O HO CH2 H OH OH H HO OH H OH HO CH2 H O OH OH H HO H H OH C OH C OH C OH CH 2OH D-glucose

HO C H

-D-glucopyranose

-D-glucopyranose

Important Carbohydrates * Monosaccharides

composed of three to seven carbon atoms.
1- Glucose The most abundant hexose in our diet. The building block of complex carbohydrates. Component of the disaccharides: sucrose, maltose and lactose. Found in the polysaccharides: starch, cellulose and glycogen. CHO
CH2OH H H H C OH C OH C OH CH2OH HO C H H O H OH H OH H,OH

OH H

Important Carbohydrates * Monosaccharides

composed of three to seven carbon atoms.
2. Galactose Found in the disaccharide, lactose. Found in the cellular membranes of the brain and nervous system. Galactose is the C-4 epimer of glucose.
CHO H C OH HO C H HO C H H C OH CH2OH HO H H OH CH2OH O H OH H H,OH

Important Carbohydrates * Monosaccharides

composed of three to seven carbon atoms.

3. Fructose Sweetest of the carbohydrates. Component of the disaccharide sucrose. Fructose is a keto sugar.

Important Carbohydrates * Disaccharides

composed of 2 monosaccharide units.

1. Maltose - malt sugar. Used in cereals, candies and Composed of two D-glucose sugars joined by an -1,4 linkage.
CH2OH H H OH OH H OH O H H O H OH H H OH CH2OH O OH H H

Important Carbohydrates * Disaccharides

composed of 2 monosaccharide units.
2. Lactose - milk sugar. Found in milk and milk products. Composed of one galactose and one glucose unit joined by a -1,4 linkage.
CH2OH OH H OH H O H H OH H OH O H H OH CH2OH O OH H H

Important Carbohydrates * Disaccharides

composed of 2 monosaccharide units.
3. Sucrose - table sugar. Product of sugar cane and sugar beets. Composed of one glucose and one fructose unit. Linkage is at both anomeric carbons.
CH2OH H H OH OH H OH O H H O OH H CH2OH O H OH CH2OH H

Important Carbohydrates * Polysaccharides

composed of many (more than 10) monosaccharide units.

1- Cellulose: Major structural material of plant cells. Consists of many glucose units joined by 1,4 linkages.

Important Carbohydrates * Polysaccharides

composed of many (more than 10) monosaccharide units. 2. Starch: Storage form of glucose found in rice wheat, potatoes, grains and cereals. Consists of many glucose units joined by -1,4 linkages. Maltose is the disaccharide starting material.

Important Carbohydrates * Polysaccharides

composed of many (more than 10) monosaccharide units. 3. Glycogen: Animal starch. Storage form of glucose found in the liver and muscle of animals. Contains many highly branched glucose units. Joined by -1,4 linkages and branched by -1,6 linkages.

Important Carbohydrates * Polysaccharides

composed of many (more than 10) monosaccharide units.

4. Dextrin: Mixture of branched and un-branched soluble polysaccharides produced by partial hydrolysis of starch by acids or amylases.

Reducing sugars
Any sugar that contains either: 1- A free aldehyde group. 2- An -hydroxy ketone group. 3- A hemiacetal linkage The presence of any of these groups allows the carbohydrate to undergo easy oxidation. If the sugar gets oxidized it causes reduction. Thus the name reducing sugar.

QUALITATIVE TESTS FOR CARBOHYDRATES

Exp. 1

Molisch Test

It is the general test for all carbohydrates. Monosaccharides give a rapid positive test. Disaccharides and polysaccharides react slower.

WHY???

Exp. 1

Molisch Test

Principle: The reaction is due to the formation of Furfural and its derivatives by the dehydrating action of acid on sugar in the event of Sugar being (poly saccharide or disaccharide) the acid first hydrolyzes it into monosaccharides and then acts as a dehydrating agent

Exp. 1

Molisch Test

The Molisch reagent dehydrates pentoses to form furfural. dehydrates hexoses to form 5hydroxymethyl furfural. The furfurals further react with naphthol present in the test reagent to produce a purple product.

Exp. 1

Molisch Test

Method: 1ml test solution + 2 drops of -naphthol mix well add conc. H2SO4 down the side of the tube to form the ring at the interface of the two layers.

- ve

+ ve

Exp. 2

Iodine Test (Test for Polysaccharides)

Poly Saccharides absorb I2 And form colour complex Starch gives blue colour while glycogen gives reddish-brown colour .

Note: On heating (poly saccharide-Iodine) complexes losses blue colour because of dissociating the complex while on cooling the blue colour again appears due to reassociation of complex

Exp. 2

Iodine Test

(Test for Polysaccharides) 1- Starch: 1/2 mL of the fresh starch solution + 1 drop of the iodine solution. A dark blue color indicates a positive test for starch. If the yellow color of the iodine reagent simply becomes diluted, no starch is present. Record the observation as positive (blue) or negative (yellow).

Exp. 2

Iodine Test
(Test for Polysaccharides)

2- Dextrin: 1/2 mL of the fresh dextrin solution + 1 drop of the iodine solution. A violet color indicates a positive test for dextrin. If the yellow color of the iodine reagent simply becomes diluted, no dextrin is present. Record the observation as positive (violet) or negative (yellow).