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
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
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
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Next class CH-02: Monosaccharides & it’s Derivates