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Carbohydrates
Prof. Dr. Khalid Hussain
Leaning objectives
• General introduction
• Medicinal and Pharmaceutical Importance
• Chemistry
• Classification
Introduction
• Chemically: Polyhydroxy aldehydes and
ketones, having hydrogen and oxygen in a ratio
of water (2:1)
e.g. Ribose (C5H10 O5) and Glucose (C6H12 O6)
• General formula Cn(H2O)n, hence, also
called hydrates of carbon
• Also include substances, which upon
hydrolysis produce polyhydroxy
aldehydes and ketones
Importance of carbohydrates
• Major source of energy (4.1C)
• Serve as stored forms of energy as
glycogen in;
–Liver
–muscles
• Involved in recognition processes of
immunoglobulins
• Are important components of brain cells e.g.
neuraminic acids, cerebrosides (Glycolipids)
and gangliosides
• Are important component of nucleic acids e.g.
pentose sugar ribose and deoxyribose
Contn’d
• Flavouring agents
• Sweetening agents
• Binders in tablets
• Disintegrators in tablets
Contn’d
• Function as anticoagulant (Heparin)
• Plasma expanders (Dextran)
• Part of parenteral nutrition
• Used as Dietary fibers e.g. Cellulose
• Protein sparing action
• Decrease breakdown of fatty acids, thus
prevent ketosis
• Used in analytical techniques: paper
chromatography, Agar-agar and starch
Classification
• Carbohydrates have been classified
into 4 main groups;
–Monosaccharides
–Disaccharides
–Oligosaccharides
–Polysaccharides
Monosaccharides
• Carbohydrates which can’t further be broken down
into simpler units by hydrolysis
• Classified according to the number of carbon atoms
present in them
– For example trioses, tetroses and hexoses
• Usually have 3-9 carbon atoms
• Further sub-classified into
– aldoses and ketoses
• Exact name is based on:
– number of carbons atoms &
– presence of aldehyde or ketone group
– i.e aldotriose or ketotriose
Aldotrioses/
Ketotrioses
C3H6O3 Glyceraldehyde and dihydroxy
acetone
Aldotetroses/
Ketotetroses
C4H8O4 Erythrose, Erythrulose
Aldopentoses/
Ketopentoses
C5H10O5 Ribose, Ribulose
Aldohexoses/
Ketohesoses
C6H12O6 Glucose, Fructose
Erythrose Ribose Ribulose
• Monosaccharides also include derivatives of
above mentioned monosaccharides e.g.
– amino sugars
– sugar alcohols
– sugar acids
– sugar esters of sulfuric acid
– sugar esters of phosphoric acid
Disaccharides
• Biose
• Formed when two monosaccharides undergo
a condensation reaction, which involves the
elimination of a water molecule
Sucrose
Oligosaccharides
• Greek word oligos, meaning "a few" and
sacchar meaning "sugar“
• Saccharide polymers containing a small
number (typically 3 to 10) of component
sugars- monosaccharaides
For example Raffinose
Polysaccharides
• Polymeric carbohydrate structures, formed
by repeating units (either mono- or di-
saccharides) joined together by glycoside
bond
• Such structures are often linear, but may
contain various degrees of branching
• Polysaccharides are often quite
heterogeneous, containing slight
modifications of the repeating units
• When all the monosaccharides in a
polysaccharide are of same type the
polysaccharide is called a
homopolysaccharide: starch and glycogen, but
when more than one type of monosaccharides
are present, they are called
heteropolysaccharides: pectin and lignin
• Polysaccharides have a general formula of
(C6H10O5)n
• Not sweet, hence called non-sugars
H O
OH
H
OHH
OH
CH2OH
H
O H
H
OHH
OH
CH2OH
H
O
HH H O
O
H
OHH
OH
CH2OH
H
H H O
H
OHH
OH
CH2OH
H
OH
HH O
O
H
OHH
OH
CH2OH
H
O
H
1
6
5
4
3
1
2
amylose
cellulose
H O
OH
H
OHH
OH
CH2OH
H
O
H
OHH
OH
CH2OH
H
O
H H O
O H
OHH
OH
CH2OH
H
H O
H
OHH
OH
CH2OH
H
H
OHH O
O H
OHH
OH
CH2OH
H
O
H H H H
1
6
5
4
3
1
2
Upon acid hydrolysis produce monosaccharides
Oxidation of glucose
• Mild oxidizing agents such as bromine water convert
glucose to gluconic acid, which is a single step
reaction
• This reaction is used to differentiate sugars having –
CHO (reducing) group and those yielding such group
Example is Fehling's solution test
• Fehling's solution is composed of equal parts
of two solutions:
1-Fehling's solution A
69.28 g copper sulfate pentahydrate
dissolved in 1 litre of distilled water
2-Fehling's Solution B
346 g potassium sodium tartrate and 120 g
sodium hydroxide in 1 litre of distilled
water
• Under alkaline conditions fructose is converted
to glucose and mannose
Fructose also give positive test
Tollens' reagent test "silver mirror"
• Tollens' reagent: when silver nitrate solution is
treated with NaOH, it forms precipitate and
then NH4OH is added till the precipitate is
dissolved-[Ag(NH3)2]+
• The diammine silver complex is an oxidizing
agent, which is itself reduced to silver metal

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Carbohydrate 1 --Sir Khalid (Biochem)

  • 2. Leaning objectives • General introduction • Medicinal and Pharmaceutical Importance • Chemistry • Classification
  • 3. Introduction • Chemically: Polyhydroxy aldehydes and ketones, having hydrogen and oxygen in a ratio of water (2:1) e.g. Ribose (C5H10 O5) and Glucose (C6H12 O6)
  • 4. • General formula Cn(H2O)n, hence, also called hydrates of carbon • Also include substances, which upon hydrolysis produce polyhydroxy aldehydes and ketones
  • 5. Importance of carbohydrates • Major source of energy (4.1C) • Serve as stored forms of energy as glycogen in; –Liver –muscles
  • 6. • Involved in recognition processes of immunoglobulins • Are important components of brain cells e.g. neuraminic acids, cerebrosides (Glycolipids) and gangliosides • Are important component of nucleic acids e.g. pentose sugar ribose and deoxyribose
  • 7. Contn’d • Flavouring agents • Sweetening agents • Binders in tablets • Disintegrators in tablets
  • 8. Contn’d • Function as anticoagulant (Heparin) • Plasma expanders (Dextran) • Part of parenteral nutrition • Used as Dietary fibers e.g. Cellulose • Protein sparing action • Decrease breakdown of fatty acids, thus prevent ketosis
  • 9. • Used in analytical techniques: paper chromatography, Agar-agar and starch
  • 10. Classification • Carbohydrates have been classified into 4 main groups; –Monosaccharides –Disaccharides –Oligosaccharides –Polysaccharides
  • 11. Monosaccharides • Carbohydrates which can’t further be broken down into simpler units by hydrolysis • Classified according to the number of carbon atoms present in them – For example trioses, tetroses and hexoses
  • 12. • Usually have 3-9 carbon atoms • Further sub-classified into – aldoses and ketoses • Exact name is based on: – number of carbons atoms & – presence of aldehyde or ketone group – i.e aldotriose or ketotriose
  • 13. Aldotrioses/ Ketotrioses C3H6O3 Glyceraldehyde and dihydroxy acetone Aldotetroses/ Ketotetroses C4H8O4 Erythrose, Erythrulose Aldopentoses/ Ketopentoses C5H10O5 Ribose, Ribulose Aldohexoses/ Ketohesoses C6H12O6 Glucose, Fructose Erythrose Ribose Ribulose
  • 14. • Monosaccharides also include derivatives of above mentioned monosaccharides e.g. – amino sugars – sugar alcohols – sugar acids – sugar esters of sulfuric acid – sugar esters of phosphoric acid
  • 15. Disaccharides • Biose • Formed when two monosaccharides undergo a condensation reaction, which involves the elimination of a water molecule Sucrose
  • 16. Oligosaccharides • Greek word oligos, meaning "a few" and sacchar meaning "sugar“ • Saccharide polymers containing a small number (typically 3 to 10) of component sugars- monosaccharaides For example Raffinose
  • 17. Polysaccharides • Polymeric carbohydrate structures, formed by repeating units (either mono- or di- saccharides) joined together by glycoside bond • Such structures are often linear, but may contain various degrees of branching • Polysaccharides are often quite heterogeneous, containing slight modifications of the repeating units
  • 18. • When all the monosaccharides in a polysaccharide are of same type the polysaccharide is called a homopolysaccharide: starch and glycogen, but when more than one type of monosaccharides are present, they are called heteropolysaccharides: pectin and lignin • Polysaccharides have a general formula of (C6H10O5)n • Not sweet, hence called non-sugars
  • 19. H O OH H OHH OH CH2OH H O H H OHH OH CH2OH H O HH H O O H OHH OH CH2OH H H H O H OHH OH CH2OH H OH HH O O H OHH OH CH2OH H O H 1 6 5 4 3 1 2 amylose cellulose H O OH H OHH OH CH2OH H O H OHH OH CH2OH H O H H O O H OHH OH CH2OH H H O H OHH OH CH2OH H H OHH O O H OHH OH CH2OH H O H H H H 1 6 5 4 3 1 2 Upon acid hydrolysis produce monosaccharides
  • 20. Oxidation of glucose • Mild oxidizing agents such as bromine water convert glucose to gluconic acid, which is a single step reaction • This reaction is used to differentiate sugars having – CHO (reducing) group and those yielding such group
  • 21. Example is Fehling's solution test • Fehling's solution is composed of equal parts of two solutions: 1-Fehling's solution A 69.28 g copper sulfate pentahydrate dissolved in 1 litre of distilled water 2-Fehling's Solution B 346 g potassium sodium tartrate and 120 g sodium hydroxide in 1 litre of distilled water
  • 22.
  • 23. • Under alkaline conditions fructose is converted to glucose and mannose Fructose also give positive test
  • 24. Tollens' reagent test "silver mirror" • Tollens' reagent: when silver nitrate solution is treated with NaOH, it forms precipitate and then NH4OH is added till the precipitate is dissolved-[Ag(NH3)2]+ • The diammine silver complex is an oxidizing agent, which is itself reduced to silver metal