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• Carbohydrates are a group of organic compounds
consisting of C, H, O usually in the ratio of 1: 2: 1
and include such well known compounds as sugars,
starch, cellulose etc.
• Previously, the carbohydrates were regarded as
hydrates of carbon and corresponded to general
formula (C.H2O) n. Some carbohydrates also contain
nitrogen, phosphorus, or sulfur.
• Carbohydrates are
broadly defined as
polyhydroxy
aldehydes or ketones
and their derivatives
or as substances that
yields one of these
compounds
• -ose indicates sugar
• About 65% of the foods in our diet consist of
carbohydrates.
• Each day we utilize carbohydrates in foods such as
bread, pasta, potatoes, and rice.
• Other carbohydrates called disaccharides include
sucrose (table sugar) and lactose in milk.
• During digestion and cellular metabolism,
carbohydrates are converted into glucose, which is
oxidized further in our cells to provide our bodies with
energy and to provide the cells with carbon atoms for
building molecules of protein, lipids, and nucleic acids.
• In plants, a polymer of glucose called cellulose builds
the structural framework. Cellulose has other
important uses, too.
• The wood in our furniture, the pages in your notebook,
and the cotton in our clothing are made of cellulose.
Sources of Carbohydrates
• Cereals
• Wheat
• Rice
• Potatoes
• Sugarcane
• Fruits
• Bread
• Milk
Function of Carbohydrates in Cells
• Major source of energy for the cell
• Major structural component of plant cell
• Immediate energy in the form of GLUCOSE
• Reserve or stored energy in the form of GLYCOGEN
• Classification of the Carbohydrates:
• Depending upon their complexity and behaviour on
hydrolysis, the carbohydrates are classified into
following 3 categories
Monosaccharides
• The simplest of the
carbohydrates, the
monosaccharides, are either
aldehydes or ketones with two
or more hydroxyl groups.
• Monosaccharides are
colorless, crystalline solids that
are freely soluble in water but
insoluble in nonpolar solvents.
• Most have a sweet taste.
• Examples of monosaccharides
include glucose (dextrose),
fructose and galactose.
• The backbones of common monosaccharides are
unbranched carbon chains in which all the carbon
atoms are linked by single bonds.
• In the open-chain form, one of the carbon atoms is
double-bonded to an oxygen atom to form a
carbonyl group; each of the other carbon atoms has
a hydroxyl group.
• If the carbonyl group is at an end of the carbon
chain (that is, in an aldehyde goup) the
monosaccharide is an aldose.
• If the carbonyl group is at any other position (in a
ketone group) the monosaccharide is a ketose.
Classification by Carbon Atoms
Sugar Structure
formula
Aldoses Ketoses
Triose C3H6O3
Glyceraldehydes Dehydroxy
acetone
Tetroses C4H8O4
Erythrose, Threose Erthrulose
Pentoses C5H10O5
Xylose
Ribose
Arabinose
Ribulose
Hexoses C6H12O6
Glucose
Galactose
Mannose
Fructose
Steriochemistry
• Optical isomers (= enantiomers) differ from each
other in the disposition of the various atoms or
groups of atoms in space around the asymmetric
carbon atom.
• These are, in fact, the mirror image of each other.
• These may also be likened to left- and right-handed
gloves.
• One form in which H atom at carbon 2 is projected
to the left side and OH group to the right is
designated as D-form and the other form where H
atom is projected to the right side and OH group to
the left is called as L-form (note the use of small
capital letters D and L).
For example, the glyceraldehyde has only one
asymmetric carbon atom (numbered as 2) and it
can, therefore, exist in 2 isomeric forms :
Properties of monosaccharides
1. Mutarotation :
• when a monosaccharide is dissolved in water, the
optical rotatory power of the solution gradually
changes until it reaches a constant value.
• For ex : when D-glucose is dissolved in water, a specific
rotation of +112.2° is obtained, but this slowly changes
, so that at 24h the value has become +52.7°.
• This gradual change in specific rotation is known as
mutarotation.
• This phenomenon is shown by number of pentoses,
hexoses and reducing disaccharides.
2. Glucoside formation :
when D-glucose solution is treated with
methanol and HCl, two compounds are formed,
these are α – and β-D- glucosides.
Thus, formed glucosides are not reducing sugar and
also doesnot show phenomenon of mutarotation
3. Reducing power :
Sugars having free or potentially free aldehyde or
ketone group have an ability to reduce the cupric copper to
cuprous
Reducing sugar + 2 Cu++ oxidized + 2Cu+
(cupric) sugar (cuprous)
4. Oxidation / Reduction: The alcoholic OH, aldehyde (COH) or
keto (C=O) group are oxidized to carboxyl group with certain
oxidizing agents. The oxidation may be brought under mild
or with vigorous oxidizing condition
i. With mild oxidant like BrH2O : In this group only aldehyde is
oxidized to produce gluconic acid (monocarbonic). Ketoses
do not respond to this reaction.
• ii. With strong Oxidizing agent like Conc HNO3 :
Both aldehyde or ketone groups are oxidized to
yield dicarboxylic acids
• iii. Oxidation with metal hydroxides: Metal
hydroxides like Cu(OH)2, Ag OH oxidize free
aldehyde or ketone group of mutarotating sugar
and reduce themselves to lower oxides of free
metals
• Reduction: The aldehyde or ketone group present
can be reduced to its respective alcohol with
sodium amalgum.
• For ex: Fructose and glucose give the hexahydric
alcohol i.e. Sorbitol and Mannitol
• Dehydration : The monosaccharides when treated
with Conc H2SO4, it get dehydrated to from 5 –
hydroxyl – methyl furfural derivative
• Methylation or Esterification : The glucosidic and
alcoholic OH group of monosaccharides and
reducing disaccharides react with acetylating agent
like acetic anhydride in pyridine to from acetate
derivatives called esters.
Oligosaccharides
• These are compound sugars that yield 2 to 10 molecules
of the same or different monosaccharides on hydrolysis.
Accordingly, an oligosaccharide yielding 2 molecules of
monosaccharide on hydrolysis is designated as a
disaccharide, and the one yielding 3 molecules of
monosaccharide as a trisaccharide and so on.
• Disaccharides – Sucrose, Lactose, Maltose, Cellobiose,
Trehalose, Gentiobiose, Melibiose
• Trisaccharides – Rhamninose, Gentianose, Raffinose (=
Melitose), Rabinose, Melezitose
• Tetrasaccharides – Stachyose, Scorodose
• Pentasaccharide – Verbascose
Disaccharides
• Composed of 2 monosaccharides
• cells can make disaccharides by joining two
monosaccharides by biosynthesis.
• Glucose + fructose = sucrose
Table sugar
• Found naturally in plants: sugar cane, sugar beets,
honey, maple syrup
• Sucrose may be purified from plant sources into
Brown, White and Powdered Sugars.
• Glucose + galactose = lactose
• The primary sugar in milk and milk products.
• Many people have problems digesting large amounts
of lactose (lactose intolerance)
• Glucose + glucose = Maltose
• Produced when starch breaks down.
• Used naturally in fermentation reactions of alcohol
and beer manufacturing.
Trisaccharides:
Composed of three
monosaccharide ex:
Raffinose (Formed by
one mole of each i.e.
glu, fruc, galac)
Tetrasaccharides :
ex: Stachyose
(composed of two
moles of galactose one
mole of glu & one mole
of fruct)
• Polysaccharides Containing 10 or more
monosaccharide units attached together
Examples
1. Starch- digestible
2. Glycogen- digestible
3. Fiber- indigestible
Long chains of glucose units form these polysaccharides
• Cellulose gives structure to plants, fiber to our diet
• Glycogen is an energy storage sugar produced by
animals
• Liver cells synthesize glycogen after a meal to maintain
blood glucose levels
Polysaccharides
• A great majority of carbohydrates of nature occur
as polysaccharides.
• Chemically, the polysaccharides may be
distinguished into homopolysaccharides, which
yield, on hydrolysis, a single monosaccharide and
heteropolysaccharides ,which produce a mixture of
monosaccharides on hydrolysis.
• Based on their functional aspect, the
polysaccharides may be grouped under two heads:
(a) Nutrient (or digestible) polysaccharides. These act
as metabolic reserve of monosaccharides in plants
and animals, e.g., starch, glycogen and inulin.
(b) Structural (or indigestible) polysaccharides. These
serve as rigid mechanical structures in plants and
animals, e.g.,cellulose, pectin and chitin and also
hyaluronic acid and chondroitin.
Types of Polysaccharides
1. Starch
• The major digestible polysaccharide in our diet.
• The storage form of carbohydrate in plants.
• Sources: Wheat, rice, corn, rye, barley, potatoes,
tubers, yams, etc.
• Two types of plant starch:
• 1. Amylose
• 2. Amylopectin
Amylose:
It is in the form of straight chain linked together
with α- 1-4, linkages indicating 300 – 5,500 glucose
units per molecules, molecular wt range from 105 to
106.
Generally it is water soluble and gives blue colour
with iodine.
Amylopectins:
It contain beside straight chain several branched
chains, which are arranged in α—1-4 and β-1-6 linkage
units, one molecule of amylopectin contains 50,000 to
5,00,000 glucose molecules, molecular wt. range from
107 to 108, it is insoluble in water and gives purple
colour with iodine .
2. Cellulose
• form cell walls in plant
cells
• also called fiber or ruffage
• indigestible by humans
3. Glycogen
• The storage form of glucose in the body.
• Stored in the liver and muscles.
• Found in tiny amounts in meat sources.
• Not found in plants.
• Not a significant food source of carbohydrate.
Carbohydrates introduction, classification and properties

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Carbohydrates introduction, classification and properties

  • 1.
  • 2. • Carbohydrates are a group of organic compounds consisting of C, H, O usually in the ratio of 1: 2: 1 and include such well known compounds as sugars, starch, cellulose etc. • Previously, the carbohydrates were regarded as hydrates of carbon and corresponded to general formula (C.H2O) n. Some carbohydrates also contain nitrogen, phosphorus, or sulfur.
  • 3. • Carbohydrates are broadly defined as polyhydroxy aldehydes or ketones and their derivatives or as substances that yields one of these compounds • -ose indicates sugar
  • 4.
  • 5. • About 65% of the foods in our diet consist of carbohydrates. • Each day we utilize carbohydrates in foods such as bread, pasta, potatoes, and rice. • Other carbohydrates called disaccharides include sucrose (table sugar) and lactose in milk. • During digestion and cellular metabolism, carbohydrates are converted into glucose, which is oxidized further in our cells to provide our bodies with energy and to provide the cells with carbon atoms for building molecules of protein, lipids, and nucleic acids. • In plants, a polymer of glucose called cellulose builds the structural framework. Cellulose has other important uses, too. • The wood in our furniture, the pages in your notebook, and the cotton in our clothing are made of cellulose.
  • 6. Sources of Carbohydrates • Cereals • Wheat • Rice • Potatoes • Sugarcane • Fruits • Bread • Milk
  • 7. Function of Carbohydrates in Cells • Major source of energy for the cell • Major structural component of plant cell • Immediate energy in the form of GLUCOSE • Reserve or stored energy in the form of GLYCOGEN • Classification of the Carbohydrates: • Depending upon their complexity and behaviour on hydrolysis, the carbohydrates are classified into following 3 categories
  • 8.
  • 9. Monosaccharides • The simplest of the carbohydrates, the monosaccharides, are either aldehydes or ketones with two or more hydroxyl groups. • Monosaccharides are colorless, crystalline solids that are freely soluble in water but insoluble in nonpolar solvents. • Most have a sweet taste. • Examples of monosaccharides include glucose (dextrose), fructose and galactose.
  • 10. • The backbones of common monosaccharides are unbranched carbon chains in which all the carbon atoms are linked by single bonds. • In the open-chain form, one of the carbon atoms is double-bonded to an oxygen atom to form a carbonyl group; each of the other carbon atoms has a hydroxyl group. • If the carbonyl group is at an end of the carbon chain (that is, in an aldehyde goup) the monosaccharide is an aldose. • If the carbonyl group is at any other position (in a ketone group) the monosaccharide is a ketose.
  • 11. Classification by Carbon Atoms Sugar Structure formula Aldoses Ketoses Triose C3H6O3 Glyceraldehydes Dehydroxy acetone Tetroses C4H8O4 Erythrose, Threose Erthrulose Pentoses C5H10O5 Xylose Ribose Arabinose Ribulose Hexoses C6H12O6 Glucose Galactose Mannose Fructose
  • 12. Steriochemistry • Optical isomers (= enantiomers) differ from each other in the disposition of the various atoms or groups of atoms in space around the asymmetric carbon atom. • These are, in fact, the mirror image of each other. • These may also be likened to left- and right-handed gloves.
  • 13. • One form in which H atom at carbon 2 is projected to the left side and OH group to the right is designated as D-form and the other form where H atom is projected to the right side and OH group to the left is called as L-form (note the use of small capital letters D and L). For example, the glyceraldehyde has only one asymmetric carbon atom (numbered as 2) and it can, therefore, exist in 2 isomeric forms :
  • 14.
  • 15. Properties of monosaccharides 1. Mutarotation : • when a monosaccharide is dissolved in water, the optical rotatory power of the solution gradually changes until it reaches a constant value. • For ex : when D-glucose is dissolved in water, a specific rotation of +112.2° is obtained, but this slowly changes , so that at 24h the value has become +52.7°. • This gradual change in specific rotation is known as mutarotation. • This phenomenon is shown by number of pentoses, hexoses and reducing disaccharides.
  • 16. 2. Glucoside formation : when D-glucose solution is treated with methanol and HCl, two compounds are formed, these are Îą – and β-D- glucosides. Thus, formed glucosides are not reducing sugar and also doesnot show phenomenon of mutarotation
  • 17. 3. Reducing power : Sugars having free or potentially free aldehyde or ketone group have an ability to reduce the cupric copper to cuprous Reducing sugar + 2 Cu++ oxidized + 2Cu+ (cupric) sugar (cuprous) 4. Oxidation / Reduction: The alcoholic OH, aldehyde (COH) or keto (C=O) group are oxidized to carboxyl group with certain oxidizing agents. The oxidation may be brought under mild or with vigorous oxidizing condition i. With mild oxidant like BrH2O : In this group only aldehyde is oxidized to produce gluconic acid (monocarbonic). Ketoses do not respond to this reaction.
  • 18. • ii. With strong Oxidizing agent like Conc HNO3 : Both aldehyde or ketone groups are oxidized to yield dicarboxylic acids • iii. Oxidation with metal hydroxides: Metal hydroxides like Cu(OH)2, Ag OH oxidize free aldehyde or ketone group of mutarotating sugar and reduce themselves to lower oxides of free metals • Reduction: The aldehyde or ketone group present can be reduced to its respective alcohol with sodium amalgum. • For ex: Fructose and glucose give the hexahydric alcohol i.e. Sorbitol and Mannitol
  • 19. • Dehydration : The monosaccharides when treated with Conc H2SO4, it get dehydrated to from 5 – hydroxyl – methyl furfural derivative • Methylation or Esterification : The glucosidic and alcoholic OH group of monosaccharides and reducing disaccharides react with acetylating agent like acetic anhydride in pyridine to from acetate derivatives called esters.
  • 20.
  • 21. Oligosaccharides • These are compound sugars that yield 2 to 10 molecules of the same or different monosaccharides on hydrolysis. Accordingly, an oligosaccharide yielding 2 molecules of monosaccharide on hydrolysis is designated as a disaccharide, and the one yielding 3 molecules of monosaccharide as a trisaccharide and so on. • Disaccharides – Sucrose, Lactose, Maltose, Cellobiose, Trehalose, Gentiobiose, Melibiose • Trisaccharides – Rhamninose, Gentianose, Raffinose (= Melitose), Rabinose, Melezitose • Tetrasaccharides – Stachyose, Scorodose • Pentasaccharide – Verbascose
  • 22.
  • 23. Disaccharides • Composed of 2 monosaccharides • cells can make disaccharides by joining two monosaccharides by biosynthesis. • Glucose + fructose = sucrose Table sugar • Found naturally in plants: sugar cane, sugar beets, honey, maple syrup • Sucrose may be purified from plant sources into Brown, White and Powdered Sugars.
  • 24. • Glucose + galactose = lactose • The primary sugar in milk and milk products. • Many people have problems digesting large amounts of lactose (lactose intolerance) • Glucose + glucose = Maltose • Produced when starch breaks down. • Used naturally in fermentation reactions of alcohol and beer manufacturing.
  • 25.
  • 26. Trisaccharides: Composed of three monosaccharide ex: Raffinose (Formed by one mole of each i.e. glu, fruc, galac) Tetrasaccharides : ex: Stachyose (composed of two moles of galactose one mole of glu & one mole of fruct)
  • 27. • Polysaccharides Containing 10 or more monosaccharide units attached together Examples 1. Starch- digestible 2. Glycogen- digestible 3. Fiber- indigestible Long chains of glucose units form these polysaccharides • Cellulose gives structure to plants, fiber to our diet • Glycogen is an energy storage sugar produced by animals • Liver cells synthesize glycogen after a meal to maintain blood glucose levels Polysaccharides
  • 28. • A great majority of carbohydrates of nature occur as polysaccharides. • Chemically, the polysaccharides may be distinguished into homopolysaccharides, which yield, on hydrolysis, a single monosaccharide and heteropolysaccharides ,which produce a mixture of monosaccharides on hydrolysis. • Based on their functional aspect, the polysaccharides may be grouped under two heads: (a) Nutrient (or digestible) polysaccharides. These act as metabolic reserve of monosaccharides in plants and animals, e.g., starch, glycogen and inulin.
  • 29.
  • 30. (b) Structural (or indigestible) polysaccharides. These serve as rigid mechanical structures in plants and animals, e.g.,cellulose, pectin and chitin and also hyaluronic acid and chondroitin.
  • 31. Types of Polysaccharides 1. Starch • The major digestible polysaccharide in our diet. • The storage form of carbohydrate in plants. • Sources: Wheat, rice, corn, rye, barley, potatoes, tubers, yams, etc. • Two types of plant starch: • 1. Amylose • 2. Amylopectin
  • 32. Amylose: It is in the form of straight chain linked together with Îą- 1-4, linkages indicating 300 – 5,500 glucose units per molecules, molecular wt range from 105 to 106. Generally it is water soluble and gives blue colour with iodine. Amylopectins: It contain beside straight chain several branched chains, which are arranged in α—1-4 and β-1-6 linkage units, one molecule of amylopectin contains 50,000 to 5,00,000 glucose molecules, molecular wt. range from 107 to 108, it is insoluble in water and gives purple colour with iodine .
  • 33.
  • 34. 2. Cellulose • form cell walls in plant cells • also called fiber or ruffage • indigestible by humans
  • 35. 3. Glycogen • The storage form of glucose in the body. • Stored in the liver and muscles. • Found in tiny amounts in meat sources. • Not found in plants. • Not a significant food source of carbohydrate.