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Carbohydrates
Dr. N. G. Telkapalliwar
(M.Sc., NET, SET, Ph.D., PGD-NSNT)
Associate Professor
Department of Chemistry,
Dr. Ambedkar College, Deekshabhoomi, Nagpur
 Definition, classification and reaction of glucose.
 Mechanism of osazone formation.
 Determination of structure of glucose.
 Determination of ring size of monosaccharides.
 Epimerisation and mutarotation
 Conversion of glucose into fructose and vice-versa.
 Chain lengthening and shortening of aldoses (Wohl’s degradation).
 Introduction to structures of
Maltose, Sucrose, Lactose, Starch , Cellulose, Ribose and Deoxyribose
Carbohydrates
What are Carbohydrates?
• Carbohydrates are organic biomolecules abundantly
present in the nature.
• Found in the cells of plants and animals.
• The term “Carbohydrate” was coined by “Karl Schmidt”.
Carbohydrates Biosynthesis
• Carbohydrates are predominantly biosynthesized by plants
through photosynthesis.
• Glucose is synthesized in plants from CO2, H2O, and solar
energy from the sun.
chlorophyll
6 CO2 + 6 H2O C6H12O6 + 6 O2
Sunlight Glucose
(Simple Carbohydrate)
(+)-Glucose Starch or Cellulose
(Complex Carbohydrates Of Plants)
Photosynthesis
• Carbohydrate (Glucose) is oxidized in living cells of
human body to produce CO2, H2O, and energy(ATP).
• Carbohydrates provide skeletal framework to cells ,
tissues, and organs of body.(Structural role)
• Carbohydrates are associated to many other roles
with human beings.
DEFINITION
OF
CARBOHYDRATES
Old Definition of Carbohydrates
• Empirical formula/General formula for simple carbohydrates :
Cn (H2O)n
• Where n = number of carbon atom present in carbohydrate
structure.
• Old Definition-
Carbohydrates are “Hydrates of Carbon”
• Old definition is not valid since-
• Certain Carbohydrates –
Rhamnose did not fit in the empirical formula of carbohydrates.
• Certain non Carbohydrates –
Lactate and Acetate fitted in the empirical formulae.
Observe the following chemical
structures of
simple Carbohydrates:
Glucose and Fructose
Aldose
(e.g., Glucose) have an
aldehyde group at one
end.
Ketose
(e.g., Fructose) have a
ketone group, usually
at C2.
C
C OH
H
C H
HO
C OH
H
C OH
H
CH2OH
D-glucose
O
H
C H
HO
C OH
H
C OH
H
CH2OH
CH2OH
C O
D-fructose
• Simple Carbohydrates has many Hydroxyl groups
(Polyhydroxy).
• Simple Carbohydrates has carbonyl/ functional groups as
Aldehyde or Ketone.
• Simple Carbohydrates(Glucose/Fructose) repeatedly linked to
form its condensed complex carbohydrates for ex Starch
• The hydroxyl groups may be free or substituted by any
other groups.
• Simple Carbohydrates on chemical reactions produces
derivatives of Carbohydrates.
New Definition
of
Carbohydrates
Carbohydrates are organic biomolecules,
abundantly present in the plant and animal
bodies, chemically composed of Polyhydroxy
Aldehyde or Polyhydroxy Ketone, their
condensed products or their derivatives.
• Depending Upon Number of Saccharide Units
• Four Main Classes of Carbohydrates
• Monosaccharides
(1 Saccharide Unit)
• Disaccharides
(2 Saccharide Units)
• Oligosaccharides
( 3-9 Saccharide Units)
• Polysaccharides
( More than 10 Saccharide Units)
Classification Of Carbohydrates
Monosaccharides Sub Classification
• Monosaccharides are sub classified on
the basis of:
–Functional Group
–Number of Carbon atoms.
Number of
Carbon Atoms Aldoses
(Aldehyde-CHO)
Ketoses
(Ketone -C=O)
3
Triose
Aldo Triose
Glyceraldehyde
Keto Triose
Di HydroxyAcetone
4
Tetrose
Aldo Tetrose
Erythrose
Keto Tetrulose
Erythrulose
5
Pentose
Aldo Pentose
Ribose, Xylose, Arabinose
Keto Pentulose
Ribulose, Xylulose
6
Hexose
Aldo Hexose
Glucose, Galactose ,Mannose
Keto Hexose
Fructose
7
Heptose
Aldo Heptose
SedoHeptose
Keto Heptulose
SedoHeptulose
Disaccharides
• Disaccharides has 2 Monosaccharide units linked
by glycosidic bond.
• Disaccharides may be reducing or non reducing
Types of Disaccharides
Reducing Disaccharides –
Lactose
Maltose
Non reducing Disaccharides-
Sucrose
Oligosaccharides Sub Classification
• Oligosaccharides has 3-9 Monosaccharide units linked by
glycosidic bonds.
• Oligosaccharides are sub classified on the basis of number
of Saccharide units.
Number of
Monosaccharide Units
Type Of Oligosaccharides
(3-10 Monosaccharide Units )
3 Trisaccharides
Maltotriose
Raffinose
4 Tetrasaccharides
Stachyose
5 Pentasaccharides
Verbascose
Polysaccharide Sub Classification
• Polysaccharides/ Glycans contain more than 10, same/
different Monosaccharide units linked by glycosidic linkages.
• Homopolysaccharides/Homoglycans-
Contains more than 10 same repeating units.
Example: Starch, Cellulose
• Heteropolysaccharides / Heteroglycans-
Contains more than 10, different repeating units.
Example: Inulin
Types of Polysaccharides
POLYSACCHARIDES/ Glycans
( More than 10 Monosaccharide Units )
Homopolysaccharides/ Homoglycans
( > 10 Same Repeating Units )
Glucosans
(Repeating Unit of
Glucose/Polymer of Glucose)
Starch
Glycogen
Cellulose
Dextrin
Dextran
Fructosans
(Repeating Unit of
Fructose/Polymer
of Fructose)
Inulin
Hetero Polysaccharides
( More than 10 Different Repeating Units )
Animal Heteropolysacchrides
Mucopolysaccharides (MPS)
OR
Glycosaminoglycans (GAGs)
Types And Examples of Mucopolysaccharides
Acidic Non Sulfated MPS:
Hyaluronic Acid
Acidic Sulfated MPS:
Heparin
Heparan Sulfate
Chondritin Sulfate
Dermatan Sulfate
Keratan Sulfate
Plant Heteropolysaccharides
• Agar
• Pectin
• Lignin
• Gum
What are Sugars?
• Sugars are chemically simple Carbohydrates
Monosaccharides and Disaccharides.
• Sugars are Crystalline Solid substances.
• Soluble in water
• Sweet in taste
• Structure possess asymmetric /chiral
carbon atoms/stereogenic centers.
Types Of Sugars
• Reducing Sugars
• Non Reducing Sugars
Reducing Sugar
• Sugar structure possessing free or potential(reactive)
aldehyde or ketone group is termed as reducing sugar.
• Reducing sugars show reducing property efficiently in
alkaline medium and reduces certain metallic ions as-
Cu++;Bi++;Fe+++
Reducing Sugars answer following tests positive
 Benedict’s Test
 Fehling’s test
 Nylander’s Test
 Form Osazones.
 Reducing Shows Mutarotation (Change in Optical activity)
All Monosaccharides are reducing sugars.
Monosaccharides are strong reducing agents.
Monosaccharides–Ribose, Glucose, Galactose, Fructose.
Disaccharides are weak reducing agents.
Reducing Disaccharides- Lactose, Maltose.
Examples Of Reducing Sugars
Non Reducing Sugars
• Sugar structure not possessing free
or potential aldehyde or ketone
group in its structure is termed as
non reducing sugar.
• Non reducing sugar does not show
reducing property and do not reduce
metallic ions.
• Non reducing sugars give following reducing
tests negative.
• Benedict’s Test
• Fehling’s test
• Nylander’s Test
• Do not form Osazones
• Non Reducing sugars do not exhibit
Mutarotation (Change in Optical activity)
Examples of Non reducing Sugars
• Non reducing Disaccharides.
–Sucrose (Biomedically Important)
–Trehalose (Glu-Glu linked with α(1-
1) glycosidic bond)
• Polysaccharides/Complex
Carbohydrates are Non reducing.
Chemical reactions of
Glucose
Structure of Carbohydrates
-D-Glucose -D-Glucose
-D-Fructose
-D-Fructose
Maltose
Sucrose
Lactose
Cellulose
Starch
Carbohydrates

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Carbohydrates

  • 1. Carbohydrates Dr. N. G. Telkapalliwar (M.Sc., NET, SET, Ph.D., PGD-NSNT) Associate Professor Department of Chemistry, Dr. Ambedkar College, Deekshabhoomi, Nagpur
  • 2.  Definition, classification and reaction of glucose.  Mechanism of osazone formation.  Determination of structure of glucose.  Determination of ring size of monosaccharides.  Epimerisation and mutarotation  Conversion of glucose into fructose and vice-versa.  Chain lengthening and shortening of aldoses (Wohl’s degradation).  Introduction to structures of Maltose, Sucrose, Lactose, Starch , Cellulose, Ribose and Deoxyribose Carbohydrates
  • 3. What are Carbohydrates? • Carbohydrates are organic biomolecules abundantly present in the nature. • Found in the cells of plants and animals. • The term “Carbohydrate” was coined by “Karl Schmidt”. Carbohydrates Biosynthesis • Carbohydrates are predominantly biosynthesized by plants through photosynthesis. • Glucose is synthesized in plants from CO2, H2O, and solar energy from the sun.
  • 4. chlorophyll 6 CO2 + 6 H2O C6H12O6 + 6 O2 Sunlight Glucose (Simple Carbohydrate) (+)-Glucose Starch or Cellulose (Complex Carbohydrates Of Plants) Photosynthesis
  • 5. • Carbohydrate (Glucose) is oxidized in living cells of human body to produce CO2, H2O, and energy(ATP). • Carbohydrates provide skeletal framework to cells , tissues, and organs of body.(Structural role) • Carbohydrates are associated to many other roles with human beings.
  • 7. Old Definition of Carbohydrates • Empirical formula/General formula for simple carbohydrates : Cn (H2O)n • Where n = number of carbon atom present in carbohydrate structure. • Old Definition- Carbohydrates are “Hydrates of Carbon” • Old definition is not valid since- • Certain Carbohydrates – Rhamnose did not fit in the empirical formula of carbohydrates. • Certain non Carbohydrates – Lactate and Acetate fitted in the empirical formulae.
  • 8. Observe the following chemical structures of simple Carbohydrates: Glucose and Fructose
  • 9. Aldose (e.g., Glucose) have an aldehyde group at one end. Ketose (e.g., Fructose) have a ketone group, usually at C2. C C OH H C H HO C OH H C OH H CH2OH D-glucose O H C H HO C OH H C OH H CH2OH CH2OH C O D-fructose
  • 10. • Simple Carbohydrates has many Hydroxyl groups (Polyhydroxy). • Simple Carbohydrates has carbonyl/ functional groups as Aldehyde or Ketone. • Simple Carbohydrates(Glucose/Fructose) repeatedly linked to form its condensed complex carbohydrates for ex Starch • The hydroxyl groups may be free or substituted by any other groups. • Simple Carbohydrates on chemical reactions produces derivatives of Carbohydrates.
  • 11. New Definition of Carbohydrates Carbohydrates are organic biomolecules, abundantly present in the plant and animal bodies, chemically composed of Polyhydroxy Aldehyde or Polyhydroxy Ketone, their condensed products or their derivatives.
  • 12. • Depending Upon Number of Saccharide Units • Four Main Classes of Carbohydrates • Monosaccharides (1 Saccharide Unit) • Disaccharides (2 Saccharide Units) • Oligosaccharides ( 3-9 Saccharide Units) • Polysaccharides ( More than 10 Saccharide Units) Classification Of Carbohydrates
  • 13.
  • 14.
  • 15. Monosaccharides Sub Classification • Monosaccharides are sub classified on the basis of: –Functional Group –Number of Carbon atoms.
  • 16. Number of Carbon Atoms Aldoses (Aldehyde-CHO) Ketoses (Ketone -C=O) 3 Triose Aldo Triose Glyceraldehyde Keto Triose Di HydroxyAcetone 4 Tetrose Aldo Tetrose Erythrose Keto Tetrulose Erythrulose 5 Pentose Aldo Pentose Ribose, Xylose, Arabinose Keto Pentulose Ribulose, Xylulose 6 Hexose Aldo Hexose Glucose, Galactose ,Mannose Keto Hexose Fructose 7 Heptose Aldo Heptose SedoHeptose Keto Heptulose SedoHeptulose
  • 17. Disaccharides • Disaccharides has 2 Monosaccharide units linked by glycosidic bond. • Disaccharides may be reducing or non reducing Types of Disaccharides Reducing Disaccharides – Lactose Maltose Non reducing Disaccharides- Sucrose
  • 18. Oligosaccharides Sub Classification • Oligosaccharides has 3-9 Monosaccharide units linked by glycosidic bonds. • Oligosaccharides are sub classified on the basis of number of Saccharide units. Number of Monosaccharide Units Type Of Oligosaccharides (3-10 Monosaccharide Units ) 3 Trisaccharides Maltotriose Raffinose 4 Tetrasaccharides Stachyose 5 Pentasaccharides Verbascose
  • 19. Polysaccharide Sub Classification • Polysaccharides/ Glycans contain more than 10, same/ different Monosaccharide units linked by glycosidic linkages. • Homopolysaccharides/Homoglycans- Contains more than 10 same repeating units. Example: Starch, Cellulose • Heteropolysaccharides / Heteroglycans- Contains more than 10, different repeating units. Example: Inulin Types of Polysaccharides
  • 20. POLYSACCHARIDES/ Glycans ( More than 10 Monosaccharide Units ) Homopolysaccharides/ Homoglycans ( > 10 Same Repeating Units ) Glucosans (Repeating Unit of Glucose/Polymer of Glucose) Starch Glycogen Cellulose Dextrin Dextran Fructosans (Repeating Unit of Fructose/Polymer of Fructose) Inulin
  • 21. Hetero Polysaccharides ( More than 10 Different Repeating Units ) Animal Heteropolysacchrides Mucopolysaccharides (MPS) OR Glycosaminoglycans (GAGs)
  • 22. Types And Examples of Mucopolysaccharides Acidic Non Sulfated MPS: Hyaluronic Acid Acidic Sulfated MPS: Heparin Heparan Sulfate Chondritin Sulfate Dermatan Sulfate Keratan Sulfate
  • 23. Plant Heteropolysaccharides • Agar • Pectin • Lignin • Gum
  • 24. What are Sugars? • Sugars are chemically simple Carbohydrates Monosaccharides and Disaccharides. • Sugars are Crystalline Solid substances. • Soluble in water • Sweet in taste • Structure possess asymmetric /chiral carbon atoms/stereogenic centers.
  • 25. Types Of Sugars • Reducing Sugars • Non Reducing Sugars Reducing Sugar • Sugar structure possessing free or potential(reactive) aldehyde or ketone group is termed as reducing sugar. • Reducing sugars show reducing property efficiently in alkaline medium and reduces certain metallic ions as- Cu++;Bi++;Fe+++
  • 26. Reducing Sugars answer following tests positive  Benedict’s Test  Fehling’s test  Nylander’s Test  Form Osazones.  Reducing Shows Mutarotation (Change in Optical activity) All Monosaccharides are reducing sugars. Monosaccharides are strong reducing agents. Monosaccharides–Ribose, Glucose, Galactose, Fructose. Disaccharides are weak reducing agents. Reducing Disaccharides- Lactose, Maltose. Examples Of Reducing Sugars
  • 27. Non Reducing Sugars • Sugar structure not possessing free or potential aldehyde or ketone group in its structure is termed as non reducing sugar. • Non reducing sugar does not show reducing property and do not reduce metallic ions.
  • 28. • Non reducing sugars give following reducing tests negative. • Benedict’s Test • Fehling’s test • Nylander’s Test • Do not form Osazones • Non Reducing sugars do not exhibit Mutarotation (Change in Optical activity)
  • 29. Examples of Non reducing Sugars • Non reducing Disaccharides. –Sucrose (Biomedically Important) –Trehalose (Glu-Glu linked with α(1- 1) glycosidic bond) • Polysaccharides/Complex Carbohydrates are Non reducing.