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Chemistry and Functions
of Carbohydrates
C-XI, Unit-IV
Dr. Bharati Behera
Faculty in Chemistry
Rama Devi Women’s University
Vidya Vihar
Bhubaneswar-751022
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)
 Animals and Human beings cannot biosynthesize
Carbohydrates predominantly.
 To fulfill metabolic and structural role in human
beings,
 It is essential to ingest carbohydrates through
food substances of plant and animal origin.
 Thus Carbohydrates are chief constituents of
human food.
 R.D.A for Dietary Carbohydrates = 400-600
gm/day.
 However in a critical condition when cells are deprived of
Glucose
 Human body biosynthesizes Glucose using the non
carbohydrate precursors present in body via
Gluconeogenesis.
 Carbohydrates serve as primary source of energy/Fuel of
body
( Metabolic role).
 Carbohydrate (Glucose) is oxidized in living cells of
human body to produce CO2, H2O, and
energy(ATP).
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.
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, Inulin.
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.
Classification Of Carbohydrates
 Depending Upon Number of Saccharide Units
 Four Main Classes of Carbohydrates
 Monosaccharides
(1 Saccharide Unit)
 Disaccharides
(2 Saccharide Units)
 Oligosaccharides
( 3-10 Saccharide Units)
 Polysaccharides
( More than 10 Saccharide Units)
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
Type Of Disaccharides
 Reducing Disaccharides –
 Lactose (Glu-Gal)
 Maltose (Glu-Glu)
 Non reducing Disaccharides-
 Sucrose(Glu-Fru)
Oligosaccharides Sub Classification
 Oligosaccharides has 3-10 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 (Glu-Glu-Glu)
Raffinose (Glu-Fru-Gal)
4 Tetrasaccharides
Stachyose (Glu-Fru-2Gal)
5 Pentasaccharides
Verbascose (Glu-Fru-3Gal)
Polysaccharide Sub Classification
 Polysaccharides/ Glycans
contain more than 10, same/ different
Monosaccharide units linked by glycosidic
linkages.
Types of Polysaccharides
 Homopolysaccharides/
Homoglycans-
Contains more than 10 same repeating units.
 Heteropolysaccharides / Heteroglycans-
Contains more than 10, different repeating units.
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
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.
The carbonyl/ functional groups
of Carbohydrates may be
present as free or bound
(involved in glycosidic bonds).
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)
Examples Of Reducing Sugars
 All Monosaccharides are reducing sugars.
 Monosaccharides are strong reducing agents.
 Monosaccharides–
 Ribose, Glucose, Galactose, Fructose.
 Disaccharides are weak reducing agents.
 Reducing Disaccharides-
 Lactose, Maltose.
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.
Sugar/Sugar Derivatives Percent
Sweetness
Glucose 75
Fructose
(Sweetest Sugar)
175
(Highest)
Galactose 30
Sucrose 100
Lactose 20
Maltose 30
Xylitol 250
Non Carbohydrate
Synthetic Sweetners
Percent Sweetness
Saccharin 45,000 times
Aspartame
(Asp-Phe)
18,000 times
Thaumatin and
Monellin
10,000 times
Cyclamate 1000 times
 All Carbohydrates except Di Hydroxy
Acetone(DHA) possess asymmetric carbon
atoms in their structure.
 Presence of Asymmetric carbon atoms
confer two properties:
 Optical Activity
 Stereoisomerism.
Optical Activity
 Optically active solutions when placed in the
tube of Polarimeter.
 If moves the plane of polarized light
toward right are dextro rotatory (d/+).
 If moves the plane of polarized light
toward left are laevo rotatory (l/-).

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carbohydrate_chemistry Bharati.pdf

  • 1. Chemistry and Functions of Carbohydrates C-XI, Unit-IV Dr. Bharati Behera Faculty in Chemistry Rama Devi Women’s University Vidya Vihar Bhubaneswar-751022
  • 2. 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”.
  • 3. 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)
  • 5.  Animals and Human beings cannot biosynthesize Carbohydrates predominantly.  To fulfill metabolic and structural role in human beings,  It is essential to ingest carbohydrates through food substances of plant and animal origin.  Thus Carbohydrates are chief constituents of human food.  R.D.A for Dietary Carbohydrates = 400-600 gm/day.
  • 6.  However in a critical condition when cells are deprived of Glucose  Human body biosynthesizes Glucose using the non carbohydrate precursors present in body via Gluconeogenesis.  Carbohydrates serve as primary source of energy/Fuel of body ( Metabolic role).  Carbohydrate (Glucose) is oxidized in living cells of human body to produce CO2, H2O, and energy(ATP).
  • 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”
  • 8. 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.
  • 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, Inulin.
  • 11. The hydroxyl groups may be free or substituted by any other groups. Simple Carbohydrates on chemical reactions produces derivatives of Carbohydrates.
  • 12. 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.
  • 14.  Depending Upon Number of Saccharide Units  Four Main Classes of Carbohydrates  Monosaccharides (1 Saccharide Unit)  Disaccharides (2 Saccharide Units)  Oligosaccharides ( 3-10 Saccharide Units)  Polysaccharides ( More than 10 Saccharide Units)
  • 15.
  • 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
  • 18. Type Of Disaccharides  Reducing Disaccharides –  Lactose (Glu-Gal)  Maltose (Glu-Glu)  Non reducing Disaccharides-  Sucrose(Glu-Fru)
  • 19. Oligosaccharides Sub Classification  Oligosaccharides has 3-10 Monosaccharide units linked by glycosidic bonds.  Oligosaccharides are sub classified on the basis of number of Saccharide units.
  • 20. Number of Monosaccharide Units Type Of Oligosaccharides (3-10 Monosaccharide Units ) 3 Trisaccharides Maltotriose (Glu-Glu-Glu) Raffinose (Glu-Fru-Gal) 4 Tetrasaccharides Stachyose (Glu-Fru-2Gal) 5 Pentasaccharides Verbascose (Glu-Fru-3Gal)
  • 21. Polysaccharide Sub Classification  Polysaccharides/ Glycans contain more than 10, same/ different Monosaccharide units linked by glycosidic linkages.
  • 22. Types of Polysaccharides  Homopolysaccharides/ Homoglycans- Contains more than 10 same repeating units.  Heteropolysaccharides / Heteroglycans- Contains more than 10, different repeating units.
  • 23. 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
  • 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. The carbonyl/ functional groups of Carbohydrates may be present as free or bound (involved in glycosidic bonds).
  • 26. Types Of Sugars Reducing Sugars Non Reducing Sugars
  • 27. 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+++
  • 28.  Reducing Sugars answer following tests positive  Benedict’s Test  Fehling’s test  Nylander’s Test  Form Osazones.  Reducing Shows Mutarotation (Change in Optical activity)
  • 29. Examples Of Reducing Sugars  All Monosaccharides are reducing sugars.  Monosaccharides are strong reducing agents.  Monosaccharides–  Ribose, Glucose, Galactose, Fructose.  Disaccharides are weak reducing agents.  Reducing Disaccharides-  Lactose, Maltose.
  • 30. 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.
  • 31. 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)
  • 32. 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.
  • 33. Sugar/Sugar Derivatives Percent Sweetness Glucose 75 Fructose (Sweetest Sugar) 175 (Highest) Galactose 30 Sucrose 100 Lactose 20 Maltose 30 Xylitol 250
  • 34. Non Carbohydrate Synthetic Sweetners Percent Sweetness Saccharin 45,000 times Aspartame (Asp-Phe) 18,000 times Thaumatin and Monellin 10,000 times Cyclamate 1000 times
  • 35.  All Carbohydrates except Di Hydroxy Acetone(DHA) possess asymmetric carbon atoms in their structure.  Presence of Asymmetric carbon atoms confer two properties:  Optical Activity  Stereoisomerism.
  • 36. Optical Activity  Optically active solutions when placed in the tube of Polarimeter.  If moves the plane of polarized light toward right are dextro rotatory (d/+).  If moves the plane of polarized light toward left are laevo rotatory (l/-).