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Carbohydrates
By
Dr. Shasthtee Taduri
Department of Biotechnology
KAKATIYA UNIVERSITY
Warangal -506009 TS
BIOMOLECULES
GENERAL INTRODUCTION
*The living matter is composed of mainly six elements
carbon 50%
hydrogen 10%
oxygen 20%
nitrogen 8.5%
phosphorus 2.5% and
sulfur 0.8%.
These elements together constitute about 90% of the
dry weight of human body.
Several other functionally elements are
Ca 4%, K 1%, Cl 0.4%, Mg 0.1%,
Fe 0.01%, Cu 0.1%, Co 0.3%, Na 0.4%,
I 0.00005%, and Mn 0.001% .
Electrolytes are also play important role
K+, Na+, Cl-, Mg,2+ Fe2+, I-.
Biomolecules are
DNA ( Deoxynucleotide)
RNA (Ribonucleotide)
Proteins, (amminoacids),
Polysaccharides (glucose)
and Lipids. (Fatty acids)
Chemical composition for a human body weight is 65kg
the percentage of biomolecules is
protein-17%,
Fat-13.8%,
carbohydrates-1.5%,
water- 61.6% and minerarals-6.1%.
CARBOHYDRATES
* Carbohydrates are the widely distributed
compound in plants and animals kingdoms.
* Plants can be build up carbohydrates from carbon
dioxides and water in present of light in the chloroplast
cell by photosynthesis.
6CO2 + 6H2O  C6H12O6 + 6O2
* Many plants and animals contain large quantities of
carbohydrates as reserve food material
* Simples carbohydrates are also known as sugar or
saccharides and ending names of most sugars is ose.
SUN light
energy
(glucose)
General characteristics
• The term carbohydrate is derived from the
french word : hydrate de Carbone, that composed
with C, H, and O
• (CH2O)n when n = 5 then C5H10O5
• not all carbohydrates have this empirical formula:
deoxysugars, aminosugars
• carbohydrates are the most abundant organic
compounds found in nature.
Different types of carbohydrates
Mono saccharids (glucose, galactose and fructose)
Oligosaccharids (maltose, lactose and sucrose)
• Polysaccharides (starch, cellulose, inulin, gums)
• Glycoproteins and proteoglycans (hormones, blood
group substances, antibodies)
• Glycolipids (cerebrosides, gangliosides)
• Glycosides
• Mucopolysaccharides (hyaluronic acid)
• Nucleic acids
Functions
• sources of energy(dietary source)
• intermediates in the biosynthesis of other basic
biochemical's like (fats and proteins)
• associated with other, such as glycosides, vitamins and
antibiotics)
*form structural tissues in plants and in microorganisms.
. (cellulose, lignin, murein)
• participate in biological transport, cell-cell recognition,
activation of growth factors, modulation of the
immune system
carbohydrates are participate in a wide range of functions
Sugars Non Sugars
Sweet in taste Tasteless
Soluble in water Insoluble in water
Crystalline in appearence Amorphous in nature
Example: Glucose, Sucrose Example: Starch
General Classification:
Carbohydrates are 3 types
1.Based on their nature
2.Based on their Reactivity
3.Based on their number
•Based on their nature, carbohydrates are of two types
namely Sugars and Non Sugars
Reducing Sugars Reducing Non Sugars
Free Functional Groups Functional groups not free
Can participate in chemical
reactions
Will not participate in
chemical reaction
Eg: Glucose Eg: Sucrose
•Based on their Reactivity:
Carbohydrates are of two types namely
1. Reducing sugars: ( containing free functional group)
2.Non reducing: (no free functional group) carbohydrates.
•
Sugars Non Sugars
Monosaccharides Single Sugar Unit
Disaccharides Two Monosaccharide units
Oligosaccharides Three to Six
Monosaccharide units
PolySaccharides More than six
Monosaccharide units
•Based on their Composition or based on their number:
• Number of individual sugar units present, carbohydrates
are of four types namely
Classification of carbohydrates
• Monosaccharides (monoses or glycoses)
• Trioses, tetroses, pentoses, hexoses
(glucose, galactose and fructose)
• Oligosaccharides/ Disaccharides
• Di, tri, tetra, penta, up to 9 or 10
• Most important are the disaccharides
(lactose, maltose, sucrose)
• Polysaccharides or glycans
• Homopolysaccharides
• Heteropolysaccharides
• Complex carbohydrates
(starch, glycogen, cellulose)
Monosaccharides
• Monosaccharides contain a single polyhydroxy
aldehyde or ketone unit also known as simple
sugars (saccharo is Greek for“sugar”)
(e.g., glucose, galactose and fructose).
• Monosaccharides are classified according to the
number of carbon atoms they contain 1carbon
/2carbon , whether aldose CHO or ketosC=O:
• No. of Class of carbons Monosaccharide
3C triose
4C tetrose
5C pentose
6C hexose
• Most of monosaccharoids (99%) are straight
chain compounds
•
Triose : Those with 3 carbon atoms, are called triose
e.g. glyceraldehyde is an aldotriose and dihydroxy
acetone is a kettriose .
•
Significance:
These two sugars are intermediates in Glycolysis pathway
concerned with conversion of glucose to pyruvate
Glycolysis
Tetroses:
•Those with four are called tetroses such as erythrose
(Aldotetrose) and erythrulose (Ketotetrose)
Biological significant:
This is intermediate in HMP shunt pathway, associated
with Inter conversion of sugars
Pentoses
Those with five carbon atoms are called pentose's viz.
Aldopentoses such as xylose and ribose and ketopentoses
such as xylulose and ribulose etc.
•1. Ribose is an essential constituent of RNA and Vitamin riboflavin
•2. Xylose is an essential constituent of Gums and Glycoproteins
•3. Ribulose and Xylulose are intermediate in HMP shunt pathway
Hexoses:
Those with six carbon atoms are called hexoses
aldohexoses ketohexose.
*Glucose is the most readily metabolizable sugar present
in the human body. Glucose sugar is called sugar fuel of life.
*Fructose is the sweetest sugar, it’s constituent of honey.
*Mannose is an important constituent of gums and
glycoproteins
Galactose is considered as the backbone of lipids.
Properties of monosaccharids
• Differences in structures of sugars are
responsible for variations in properties
• Physical
• Crystalline form; solubility; rotatory power
• Chemical
• Reactions (oxidations, reductions, condensations)
• Physiological
• Nutritive value (human, bacterial); sweetness;
absorption
Physical Properties of Monosaccharides:
• Most monosaccharides have a sweet taste (fructose
is sweetest; 73% sweeter than sucrose).
• They are solids at room temperature.
• They are extremely soluble in water:
– Despite their high molecular weights, the
presence of large numbers of OH groups make
the monosaccharides.
– Glucose can dissolve in minute amounts of water
to make a syrup (1 g / 1 ml H2O).
D- AND L- Configuration
*Biologically active Sugars are normally belongs to
two series namely D and L Series.
*D sugars are biologically active and L sugars are
biologically inactive.
* Differentiate a D sugar from a L sugar the
penultimate carbon or the last but one carbon
atom is considered.
*In the D sugars OH group is on the penultimate
carbon is on Right
*In the L sugars OH group is on the penultimate
carbon is on left
*All D sugars are obtained from D- Glyceraldehyde
and L sugars are from L-Glyceraldehyde.
Structure of a simple aldose and a simple ketose
Organic Compounds Optical activity
Optically
Inactive (Achiral)
Optically
Active (Chiral)
Measurement of Optical
Activity :
Polarimeter
COOH
CH3
OH
H
COOH
COOH
OH
H
OH
H
Chiral And without Chiral Compounds
Many molecules are chiral with chiral centers
There are several molecules which are
Achiral with chiral centers
COOH
CH3
OH
H
COOH
COOH
OH
H
OH
H
Optical Activity:
 Most biologically important molecules are
chiral and hence are optically active.
• A levorotatory (–) substance rotates polarized light
to the left. [E.g., l-glucose; (-)-glucose]
• A dextrorotatory (+) substance rotates polarized
light to the right. [E.g., d-glucose; (+)-glucose]
• Molecules which rotate the plane of of polarized
light are optically active.
•when a compound is a equal mixture like
dextroro and levo, then the final rotation comes to
zero. Such a mixture is called Racemic Mixture.
E.g.; Glucose is dextrorotatory and Fructose is levorotatory.
Plane-Polarized Light
polarimetry
polarimetry
Magnitude of rotation depends upon:
1. the nature of the compound
2. the length of the tube (cell or sample
container) usually expressed in decimeters (dm)
3. the wavelength of the light source employed;
usually either sodium D line at 589.3 nm or
mercury vapor lamp at 546.1 nm
4. temperature of sample
5. concentration of analyte in grams per 100 ml
Plane-Polarized Light through
an Achiral Compound
COOH
COOH
OH
H
OH
H
Plane-Polarized Light through
Chiral Compound
COOH
CH3
OH
H
Specific Rotation [α]D
[α] = α / cl
a = observed rotation
c = concentration in g/mL
l = length of tube in dm
Dextro rotation designated as “d” or (+),
clockwise rotation
Laevo rotation designated as “ l ” or (-),
counter anti clockwise rotation
Specific Rotations of some
Common Organic Compounds
Compound [a]D No. of Chiral
centres
Penicillin V +233.0 3
Sucrose +66.5 10
Camphor +44.3 2
Cholesterol -31.3 8
Morphine -132.0 5
Optical isomerism
• A property exhibited by any compound whose
mirror images are non-superimposable
• Asymmetric compounds rotate plane polarized
light
Structure of a simple aldose and a simple ketose
Epimerization:
*The shift of configuration at a specific carbon atom other than
C1, C5 and C6 with respect to Glucose is called Epimerization
and the resulting compounds are called. epimers.
.
In the structure of Glucose,
when there is a shift of
configuration at 2nd carbon
atom Mannose is formed
when there is a shift of
configuration at 3rd carbon
atom Allose is formed
when there is a shift of
configuration at 4th carbon
atom Galactose is formed.
Enationmers:
carbohydrates Dr. Shasthree Taduri.ppt
carbohydrates Dr. Shasthree Taduri.ppt
carbohydrates Dr. Shasthree Taduri.ppt

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carbohydrates Dr. Shasthree Taduri.ppt

  • 1. Carbohydrates By Dr. Shasthtee Taduri Department of Biotechnology KAKATIYA UNIVERSITY Warangal -506009 TS
  • 3. *The living matter is composed of mainly six elements carbon 50% hydrogen 10% oxygen 20% nitrogen 8.5% phosphorus 2.5% and sulfur 0.8%. These elements together constitute about 90% of the dry weight of human body. Several other functionally elements are Ca 4%, K 1%, Cl 0.4%, Mg 0.1%, Fe 0.01%, Cu 0.1%, Co 0.3%, Na 0.4%, I 0.00005%, and Mn 0.001% .
  • 4. Electrolytes are also play important role K+, Na+, Cl-, Mg,2+ Fe2+, I-. Biomolecules are DNA ( Deoxynucleotide) RNA (Ribonucleotide) Proteins, (amminoacids), Polysaccharides (glucose) and Lipids. (Fatty acids) Chemical composition for a human body weight is 65kg the percentage of biomolecules is protein-17%, Fat-13.8%, carbohydrates-1.5%, water- 61.6% and minerarals-6.1%.
  • 5. CARBOHYDRATES * Carbohydrates are the widely distributed compound in plants and animals kingdoms. * Plants can be build up carbohydrates from carbon dioxides and water in present of light in the chloroplast cell by photosynthesis. 6CO2 + 6H2O  C6H12O6 + 6O2 * Many plants and animals contain large quantities of carbohydrates as reserve food material * Simples carbohydrates are also known as sugar or saccharides and ending names of most sugars is ose. SUN light energy (glucose)
  • 6. General characteristics • The term carbohydrate is derived from the french word : hydrate de Carbone, that composed with C, H, and O • (CH2O)n when n = 5 then C5H10O5 • not all carbohydrates have this empirical formula: deoxysugars, aminosugars • carbohydrates are the most abundant organic compounds found in nature.
  • 7. Different types of carbohydrates Mono saccharids (glucose, galactose and fructose) Oligosaccharids (maltose, lactose and sucrose) • Polysaccharides (starch, cellulose, inulin, gums) • Glycoproteins and proteoglycans (hormones, blood group substances, antibodies) • Glycolipids (cerebrosides, gangliosides) • Glycosides • Mucopolysaccharides (hyaluronic acid) • Nucleic acids
  • 8. Functions • sources of energy(dietary source) • intermediates in the biosynthesis of other basic biochemical's like (fats and proteins) • associated with other, such as glycosides, vitamins and antibiotics) *form structural tissues in plants and in microorganisms. . (cellulose, lignin, murein) • participate in biological transport, cell-cell recognition, activation of growth factors, modulation of the immune system carbohydrates are participate in a wide range of functions
  • 9. Sugars Non Sugars Sweet in taste Tasteless Soluble in water Insoluble in water Crystalline in appearence Amorphous in nature Example: Glucose, Sucrose Example: Starch General Classification: Carbohydrates are 3 types 1.Based on their nature 2.Based on their Reactivity 3.Based on their number •Based on their nature, carbohydrates are of two types namely Sugars and Non Sugars
  • 10. Reducing Sugars Reducing Non Sugars Free Functional Groups Functional groups not free Can participate in chemical reactions Will not participate in chemical reaction Eg: Glucose Eg: Sucrose •Based on their Reactivity: Carbohydrates are of two types namely 1. Reducing sugars: ( containing free functional group) 2.Non reducing: (no free functional group) carbohydrates. •
  • 11. Sugars Non Sugars Monosaccharides Single Sugar Unit Disaccharides Two Monosaccharide units Oligosaccharides Three to Six Monosaccharide units PolySaccharides More than six Monosaccharide units •Based on their Composition or based on their number: • Number of individual sugar units present, carbohydrates are of four types namely
  • 12. Classification of carbohydrates • Monosaccharides (monoses or glycoses) • Trioses, tetroses, pentoses, hexoses (glucose, galactose and fructose) • Oligosaccharides/ Disaccharides • Di, tri, tetra, penta, up to 9 or 10 • Most important are the disaccharides (lactose, maltose, sucrose) • Polysaccharides or glycans • Homopolysaccharides • Heteropolysaccharides • Complex carbohydrates (starch, glycogen, cellulose)
  • 13. Monosaccharides • Monosaccharides contain a single polyhydroxy aldehyde or ketone unit also known as simple sugars (saccharo is Greek for“sugar”) (e.g., glucose, galactose and fructose). • Monosaccharides are classified according to the number of carbon atoms they contain 1carbon /2carbon , whether aldose CHO or ketosC=O: • No. of Class of carbons Monosaccharide 3C triose 4C tetrose 5C pentose 6C hexose
  • 14. • Most of monosaccharoids (99%) are straight chain compounds • Triose : Those with 3 carbon atoms, are called triose e.g. glyceraldehyde is an aldotriose and dihydroxy acetone is a kettriose . • Significance: These two sugars are intermediates in Glycolysis pathway concerned with conversion of glucose to pyruvate
  • 16. Tetroses: •Those with four are called tetroses such as erythrose (Aldotetrose) and erythrulose (Ketotetrose) Biological significant: This is intermediate in HMP shunt pathway, associated with Inter conversion of sugars
  • 17. Pentoses Those with five carbon atoms are called pentose's viz. Aldopentoses such as xylose and ribose and ketopentoses such as xylulose and ribulose etc. •1. Ribose is an essential constituent of RNA and Vitamin riboflavin •2. Xylose is an essential constituent of Gums and Glycoproteins •3. Ribulose and Xylulose are intermediate in HMP shunt pathway
  • 18. Hexoses: Those with six carbon atoms are called hexoses aldohexoses ketohexose. *Glucose is the most readily metabolizable sugar present in the human body. Glucose sugar is called sugar fuel of life. *Fructose is the sweetest sugar, it’s constituent of honey. *Mannose is an important constituent of gums and glycoproteins Galactose is considered as the backbone of lipids.
  • 19. Properties of monosaccharids • Differences in structures of sugars are responsible for variations in properties • Physical • Crystalline form; solubility; rotatory power • Chemical • Reactions (oxidations, reductions, condensations) • Physiological • Nutritive value (human, bacterial); sweetness; absorption
  • 20. Physical Properties of Monosaccharides: • Most monosaccharides have a sweet taste (fructose is sweetest; 73% sweeter than sucrose). • They are solids at room temperature. • They are extremely soluble in water: – Despite their high molecular weights, the presence of large numbers of OH groups make the monosaccharides. – Glucose can dissolve in minute amounts of water to make a syrup (1 g / 1 ml H2O).
  • 21. D- AND L- Configuration *Biologically active Sugars are normally belongs to two series namely D and L Series. *D sugars are biologically active and L sugars are biologically inactive. * Differentiate a D sugar from a L sugar the penultimate carbon or the last but one carbon atom is considered. *In the D sugars OH group is on the penultimate carbon is on Right *In the L sugars OH group is on the penultimate carbon is on left *All D sugars are obtained from D- Glyceraldehyde and L sugars are from L-Glyceraldehyde.
  • 22. Structure of a simple aldose and a simple ketose
  • 23. Organic Compounds Optical activity Optically Inactive (Achiral) Optically Active (Chiral) Measurement of Optical Activity : Polarimeter COOH CH3 OH H COOH COOH OH H OH H
  • 24. Chiral And without Chiral Compounds Many molecules are chiral with chiral centers There are several molecules which are Achiral with chiral centers COOH CH3 OH H COOH COOH OH H OH H
  • 25. Optical Activity:  Most biologically important molecules are chiral and hence are optically active. • A levorotatory (–) substance rotates polarized light to the left. [E.g., l-glucose; (-)-glucose] • A dextrorotatory (+) substance rotates polarized light to the right. [E.g., d-glucose; (+)-glucose] • Molecules which rotate the plane of of polarized light are optically active. •when a compound is a equal mixture like dextroro and levo, then the final rotation comes to zero. Such a mixture is called Racemic Mixture. E.g.; Glucose is dextrorotatory and Fructose is levorotatory.
  • 27. polarimetry Magnitude of rotation depends upon: 1. the nature of the compound 2. the length of the tube (cell or sample container) usually expressed in decimeters (dm) 3. the wavelength of the light source employed; usually either sodium D line at 589.3 nm or mercury vapor lamp at 546.1 nm 4. temperature of sample 5. concentration of analyte in grams per 100 ml
  • 28. Plane-Polarized Light through an Achiral Compound COOH COOH OH H OH H
  • 29. Plane-Polarized Light through Chiral Compound COOH CH3 OH H
  • 30. Specific Rotation [α]D [α] = α / cl a = observed rotation c = concentration in g/mL l = length of tube in dm Dextro rotation designated as “d” or (+), clockwise rotation Laevo rotation designated as “ l ” or (-), counter anti clockwise rotation
  • 31. Specific Rotations of some Common Organic Compounds Compound [a]D No. of Chiral centres Penicillin V +233.0 3 Sucrose +66.5 10 Camphor +44.3 2 Cholesterol -31.3 8 Morphine -132.0 5
  • 32. Optical isomerism • A property exhibited by any compound whose mirror images are non-superimposable • Asymmetric compounds rotate plane polarized light
  • 33.
  • 34. Structure of a simple aldose and a simple ketose
  • 35. Epimerization: *The shift of configuration at a specific carbon atom other than C1, C5 and C6 with respect to Glucose is called Epimerization and the resulting compounds are called. epimers. . In the structure of Glucose, when there is a shift of configuration at 2nd carbon atom Mannose is formed when there is a shift of configuration at 3rd carbon atom Allose is formed when there is a shift of configuration at 4th carbon atom Galactose is formed.

Editor's Notes

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