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CH-01: CARBOHYDRATES
(Classification & Properties)
By
N. Santhosh Kumar
Asst. Professor
Department of Biochemistry
Shridevi Institute of Medical Sciences & Research Hospital
Polyhydroxy aldehydes or ketones or its derivatives
(or)
Polyhydroxy alcohols with free aldehyde or keto groups
1CHO
H – 2C – OH
H – 5C – OH
HO – 3C – H
H– 4C – OH HO – 4C – H
HO – 3C – H
H – 5C– OH
2C = O
1CH2OH
6 CH2OH
6CH2OH
D- Fructose
D-Glucose
•Rice, grains, cereals, fruit, green vegetables, potatoes, milk & corn
•Sugars, like table sugar and honey
CARBOHYDRATES
POLY
SACCHARIDES
OLIGO
SACCHARIDES
MONO
SACCHARIDES
Based on sugar molecules
MONO
SACCHARIDES
Classification of Carbohydrates
MONOSACCHARIDES
Simple sugars
Which cannot hydrolysis further
Classification of Monosaccharide
Based on Number of
Carbon atoms
Based on the functional group
Aldoses (-CHO-) Ketoses (C=O)
3C: Trioses Glyceraldehyde Dihydroxyacetone
4C: Tetroses Erythrose Erythrulose
5C: Pentoses Ribose, Xylose Ribulose, Xylulose
6C: Hexoses Glucose, Galactose,
Mannose
Fructose
7C: Heptoses Gluco-heptose Psedoheptulose, Mannoheptulose
D- Glucose
(Aldohexose )
It is also called dextrose
It distributed in the plant and animal
kingdom. And also the major sugar of
the life
Defect of this metabolism leads to
hyperglycemia and glycosuria
Glucose provide major source of energy
(4.1Kcal/ g)
Present in the blood as blood glucose
HO – 3C – H
H – 5C– OH
1CHO
H- 2C - OH
6CH2OH
HO –4 C – H
D- Galactose
(Aldohexose )
required by lactating mammary gland for
synthesis of lactose of milk.
Metabolic defect is Galactosaemia and
cataract
required for the synthesis of
mucopolysaccharides &glycolipids
Used as a test for liver functions called
galactose tolerance test.
HO – 3C – H
H – 5C– OH
1CHO
H- 2C - OH
6CH2OH
H – 4C – OH
D- Mannose
(Aldohexose ) Hydrolyzed product of plant gums
Constituent of many glyco-proteins
HO – 2C – H
HO – C – H
H – C – OH
C2 Epimer
CHO
CH2OH
H – C – OH
1CHO
H – 2C – OH
H – 5C – OH
HO – 3C – H
H– 4C – OH HO – 4C – H
HO – C – H
H – C– OH
H – C – OH
CHO
6CH2OH CH2OH
C4 Epimer
D-Mannose D- Galactose
D-Glucose
Epimers
D- Fructose
(Ketohexose)
“Fruit sugar /laevulose (Sweeter than
glucose)
Found in honey & fruits
Its metabolic defect leads to hereditary
fructose intolerance
Fructose converts into glucose in the liver
and metabolized
Routinely measured in the assessment of
seminal vesicle function and male factor
infertility
HO – 4C – H
HO – 3C – H
H – 5C– OH
2C = O
1CH2OH
6CH2OH
Pentose sugars
Both are important components of nucleotides & nucleic acid
Ribose-5-P involved in structural elements of coenzymes (ATP, NAD, NADP, FMN
& FAD)
HOCH2
H
H
OH OH
H
H H
H
H
OH
OH
H
HOCH2
H
OH
O O
2’
2’
1’
1’
3’
3’
4’
4’
5’
5’
Ribose sugar Deoxyribose sugar
Aldo pentose & found in
RNA
Found in DNA
CARBOHYDRATES
POLYSACCHARIDES
OLIGOSACCHARIDES
MONOSACCHARIDES
Based on sugar molecules
OLIGO SACCHARIDES
More than one & less than ten
monosaccharides held together by glycosidic
linkages to form oligosaccharides.
DISACCHARIDES
Reducing Disaccharides
Eg: Maltose (α-D-Glucose+α-D-Glu)
Lactose (β -D-Galactose + β -D-Glucose)
Non Reducing Disaccharides
Eg: Sucrose
(α-D-Glucose + β -D-fructose)
It consists of two monosaccharide units held together by
glycosidic linkages
Based on free functional group
Raffinose (Galactose + Fructose + Glucose)
Stachyose (Glucose + Fructose + 2 mole of Galactose)
Verbascose (3 mole of Galactose + Glucose + Fructose)
Tri saccharides
Tetra saccharides
Pento saccharides
CARBOHYDRATES
POLYSACCHARIDES
OLIGOSACCHARIDES
MONOSACCHARIDES
POLYSACCHARIDE
It consist of more than ten repeated units of monosaccharide or
their derivatives held together by glycosidic bonds
Homo polysaccharides
These polysaccharides contain only one type of monomeric units
held together by glycosidic linkage
Primarily concerned with two important functions
Storage Homopolysaccharide
(Starch, Inulin, Glycogen)
Structural Homopolysaccharide
(Cellulose, Chitin, Hemicellulose)
Hetero polysaccharides
These polysaccharides contains two or more different monomeric
units held together by glycosidic linkages
Glycosaminoglycans
• Heteroglycans made up of repeating units of sugar derivative
(amino sugar & uronic acid)
Eg: Hyaluronic acid
Chondroitin sulfate
Dermatan sulfate
Keratan sulfate
Heparan sulfate
(H – C –OH)4
6COOH
D- Glucuronic acid
D- Glucose
(H – C – OH)4
CH2OH
1CHO 1CHO
α- D-Glucosamine
O
H
OH
OH
CH2OH
4
3
5
6
H
OH
H
H
2
1
O
H
OH
H
CH2OH
4
3
5
6
H
OH
H
H
2
1
OH
H
α- D-N- Acetylglucosamine
NH2
HN- C- CH3
O
Amino sugar
Uronic acid
Classification of Carbohydrates
CARBOHYDRATES
Polysaccharides
Oligosaccharides
•Di-Saccharides
eg: Maltose,
Lactose,
Sucrose
•Tri-saccharides
eg: Raffinose
•Tetra-saccharides
eg: Stachyose
•Penta saccharides
eg: Verbascose
Hetero –
Polysaccharides
Eg: Hyaluronic acid
Chondroitin sulfate
Dermatan sulfate
Keratan sulfate
Heparan sulfate
Homo-
Polysaccharide
Eg: Glycogen,
- Starch
- Cellulose,
- Chitin
Monosaccharides
-Aldoses (Glucose)
- Ketoses (Fructose)
Based on sugar molecules
Based on no.of monosaccharides
Based on functional gps
Based on type of sugar moles
Properties
'D-' and 'L-form of Sugars
• 'D-' and 'L-' forms specifically the
configuration at the carbon atom that
is second from bottom (penultimate
carbon)
• 'D-'(dextrorotary,) if the hydroxyl is
on the right side (rotates the
polarization axis clockwise).
• 'L-' (levorotary,) if it is on the left
side (rotates it counter clock wise).
Pyranose/ Furanose ring structure
α- D- Glucopyranose
O
H
OH
CH2OH
4
3
5
6
H
OH
OH
H
H
2
1
H
O
3
5
2
Pyranose ring
4 1
OH
Furanose ring
O CH2OH
OH
H
OH
H
O
α-D-fructofuranose
H
CH2OH
OH
Anomers
• Diastereoisomers of related cyclic forms of sugars molecules differing in
configuration only at functional groups of carbon atoms.
Eg: α- D-Glucose & β- D-Glucose
α- D-Glucose
O
H
OH
OH
CH2OH
4
3
5
6
H
OH
OH
H
H
2
1
O
H
OH
OH
CH2OH
4
3
5
6
H
OH
OH
H
H
2
1
H
H
β- D-Glucose
Epimers
• Structures that have opposite configurations of a hydroxyl group at only
one position, except functional carbon (C1) atoms called epimer.
HO – 2C – H
HO – C – H
H – C – OH
C2 Epimer
CHO
CH2OH
H – C – OH
1CHO
H – 2C – OH
H – 5C – OH
HO – 3C – H
H– 4C – OH HO – 4C – H
HO – C – H
H – C– OH
H – C – OH
CHO
6CH2OH CH2OH
C4 Epimer
D-Mannose D- Galactose
D-Glucose
• Change in the specific optical rotation, representing the inter conversion of α & β
forms of D-sugars to an equilibrium mixture.
Example: α & β anomers of glucose have different optical rotations.
Mutarotation
Thank You
“Today's every Opportunities
can helps
to
build your tomorrow's
dreams”
Next class CH-02: Monosaccharides & it’s Derivates

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CH-01. Classification of Carbohydrates and Properties

  • 1. CH-01: CARBOHYDRATES (Classification & Properties) By N. Santhosh Kumar Asst. Professor Department of Biochemistry Shridevi Institute of Medical Sciences & Research Hospital
  • 2. Polyhydroxy aldehydes or ketones or its derivatives (or) Polyhydroxy alcohols with free aldehyde or keto groups 1CHO H – 2C – OH H – 5C – OH HO – 3C – H H– 4C – OH HO – 4C – H HO – 3C – H H – 5C– OH 2C = O 1CH2OH 6 CH2OH 6CH2OH D- Fructose D-Glucose
  • 3. •Rice, grains, cereals, fruit, green vegetables, potatoes, milk & corn •Sugars, like table sugar and honey
  • 4. CARBOHYDRATES POLY SACCHARIDES OLIGO SACCHARIDES MONO SACCHARIDES Based on sugar molecules MONO SACCHARIDES Classification of Carbohydrates
  • 6. Classification of Monosaccharide Based on Number of Carbon atoms Based on the functional group Aldoses (-CHO-) Ketoses (C=O) 3C: Trioses Glyceraldehyde Dihydroxyacetone 4C: Tetroses Erythrose Erythrulose 5C: Pentoses Ribose, Xylose Ribulose, Xylulose 6C: Hexoses Glucose, Galactose, Mannose Fructose 7C: Heptoses Gluco-heptose Psedoheptulose, Mannoheptulose
  • 7. D- Glucose (Aldohexose ) It is also called dextrose It distributed in the plant and animal kingdom. And also the major sugar of the life Defect of this metabolism leads to hyperglycemia and glycosuria Glucose provide major source of energy (4.1Kcal/ g) Present in the blood as blood glucose HO – 3C – H H – 5C– OH 1CHO H- 2C - OH 6CH2OH HO –4 C – H
  • 8. D- Galactose (Aldohexose ) required by lactating mammary gland for synthesis of lactose of milk. Metabolic defect is Galactosaemia and cataract required for the synthesis of mucopolysaccharides &glycolipids Used as a test for liver functions called galactose tolerance test. HO – 3C – H H – 5C– OH 1CHO H- 2C - OH 6CH2OH H – 4C – OH
  • 9. D- Mannose (Aldohexose ) Hydrolyzed product of plant gums Constituent of many glyco-proteins HO – 2C – H HO – C – H H – C – OH C2 Epimer CHO CH2OH H – C – OH 1CHO H – 2C – OH H – 5C – OH HO – 3C – H H– 4C – OH HO – 4C – H HO – C – H H – C– OH H – C – OH CHO 6CH2OH CH2OH C4 Epimer D-Mannose D- Galactose D-Glucose Epimers
  • 10. D- Fructose (Ketohexose) “Fruit sugar /laevulose (Sweeter than glucose) Found in honey & fruits Its metabolic defect leads to hereditary fructose intolerance Fructose converts into glucose in the liver and metabolized Routinely measured in the assessment of seminal vesicle function and male factor infertility HO – 4C – H HO – 3C – H H – 5C– OH 2C = O 1CH2OH 6CH2OH
  • 11. Pentose sugars Both are important components of nucleotides & nucleic acid Ribose-5-P involved in structural elements of coenzymes (ATP, NAD, NADP, FMN & FAD) HOCH2 H H OH OH H H H H H OH OH H HOCH2 H OH O O 2’ 2’ 1’ 1’ 3’ 3’ 4’ 4’ 5’ 5’ Ribose sugar Deoxyribose sugar Aldo pentose & found in RNA Found in DNA
  • 13. OLIGO SACCHARIDES More than one & less than ten monosaccharides held together by glycosidic linkages to form oligosaccharides.
  • 14.
  • 15. DISACCHARIDES Reducing Disaccharides Eg: Maltose (α-D-Glucose+α-D-Glu) Lactose (β -D-Galactose + β -D-Glucose) Non Reducing Disaccharides Eg: Sucrose (α-D-Glucose + β -D-fructose) It consists of two monosaccharide units held together by glycosidic linkages Based on free functional group
  • 16. Raffinose (Galactose + Fructose + Glucose) Stachyose (Glucose + Fructose + 2 mole of Galactose) Verbascose (3 mole of Galactose + Glucose + Fructose) Tri saccharides Tetra saccharides Pento saccharides
  • 18. POLYSACCHARIDE It consist of more than ten repeated units of monosaccharide or their derivatives held together by glycosidic bonds
  • 19. Homo polysaccharides These polysaccharides contain only one type of monomeric units held together by glycosidic linkage
  • 20. Primarily concerned with two important functions Storage Homopolysaccharide (Starch, Inulin, Glycogen) Structural Homopolysaccharide (Cellulose, Chitin, Hemicellulose)
  • 21. Hetero polysaccharides These polysaccharides contains two or more different monomeric units held together by glycosidic linkages
  • 22. Glycosaminoglycans • Heteroglycans made up of repeating units of sugar derivative (amino sugar & uronic acid) Eg: Hyaluronic acid Chondroitin sulfate Dermatan sulfate Keratan sulfate Heparan sulfate
  • 23. (H – C –OH)4 6COOH D- Glucuronic acid D- Glucose (H – C – OH)4 CH2OH 1CHO 1CHO α- D-Glucosamine O H OH OH CH2OH 4 3 5 6 H OH H H 2 1 O H OH H CH2OH 4 3 5 6 H OH H H 2 1 OH H α- D-N- Acetylglucosamine NH2 HN- C- CH3 O Amino sugar Uronic acid
  • 24. Classification of Carbohydrates CARBOHYDRATES Polysaccharides Oligosaccharides •Di-Saccharides eg: Maltose, Lactose, Sucrose •Tri-saccharides eg: Raffinose •Tetra-saccharides eg: Stachyose •Penta saccharides eg: Verbascose Hetero – Polysaccharides Eg: Hyaluronic acid Chondroitin sulfate Dermatan sulfate Keratan sulfate Heparan sulfate Homo- Polysaccharide Eg: Glycogen, - Starch - Cellulose, - Chitin Monosaccharides -Aldoses (Glucose) - Ketoses (Fructose) Based on sugar molecules Based on no.of monosaccharides Based on functional gps Based on type of sugar moles
  • 26. 'D-' and 'L-form of Sugars • 'D-' and 'L-' forms specifically the configuration at the carbon atom that is second from bottom (penultimate carbon) • 'D-'(dextrorotary,) if the hydroxyl is on the right side (rotates the polarization axis clockwise). • 'L-' (levorotary,) if it is on the left side (rotates it counter clock wise).
  • 27. Pyranose/ Furanose ring structure α- D- Glucopyranose O H OH CH2OH 4 3 5 6 H OH OH H H 2 1 H O 3 5 2 Pyranose ring 4 1 OH Furanose ring O CH2OH OH H OH H O α-D-fructofuranose H CH2OH OH
  • 28. Anomers • Diastereoisomers of related cyclic forms of sugars molecules differing in configuration only at functional groups of carbon atoms. Eg: α- D-Glucose & β- D-Glucose α- D-Glucose O H OH OH CH2OH 4 3 5 6 H OH OH H H 2 1 O H OH OH CH2OH 4 3 5 6 H OH OH H H 2 1 H H β- D-Glucose
  • 29. Epimers • Structures that have opposite configurations of a hydroxyl group at only one position, except functional carbon (C1) atoms called epimer. HO – 2C – H HO – C – H H – C – OH C2 Epimer CHO CH2OH H – C – OH 1CHO H – 2C – OH H – 5C – OH HO – 3C – H H– 4C – OH HO – 4C – H HO – C – H H – C– OH H – C – OH CHO 6CH2OH CH2OH C4 Epimer D-Mannose D- Galactose D-Glucose
  • 30. • Change in the specific optical rotation, representing the inter conversion of α & β forms of D-sugars to an equilibrium mixture. Example: α & β anomers of glucose have different optical rotations. Mutarotation
  • 31.
  • 32. Thank You “Today's every Opportunities can helps to build your tomorrow's dreams” Next class CH-02: Monosaccharides & it’s Derivates