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Carbohydrates



Dr. Khalid Hussain
Introduction
• Chemically: Polyhydroxy aldehydes and ketones
• Have hydrogen and oxygen in a ratio of water
  (2:1)
  Ribose (C5H10O5) and Glucose (C6H12O6)
• General formula Cn(H2O)n.Hence, also
  called hydrates of carbon

• Substances which are converted into
  polyhydroxy aldehydes and ketones
  after hydrolysis
Importance of carbohydrates
• Provide major source of energy (4.1C)
• Serve also as stored forms of energy as
  glycogen in liver and muscles
• Protein sparing action
• Reduce breakdown of fatty acids and
  preventing ketosis
• Involved in biological recognition processes of
  immunoglobulin
Contn’d
• Flavoring and Sweetening agents
• Dietary fiber (Cellulose)
• Important components of brain cells as
  neuraminic acids, cerebrosides (Glycolipids)
  and gangliosides
• Important component of nucleic acids as
  pentose sugars - ribose and deoxyribose
Contn’d
• Function as physiological anticoagulant
  (Heparin)
• Plasma expanders (Dextran)
• Parenteral nutrition
• Binders in tablets
• Disintegrators in tablets
• Analytical techniques: Agar agar and starch
• Diagnostic markers
Classification
• Have been classified into 4 main
  groups
  – Monosaccharides
  – Disaccharides
  – Oligosaccharides
  – Polysaccharides
Monosaccharides
• Carbohydrates which can’t further be broken down
  into simpler units by acid 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 groups
  – i.e aldotriose or ketotriose
Aldotrioses/       C3 H 6 O 3   Glyceraldehyde and dihydroxy
ketotrioses                     acetone
Aldotetroses/      C4 H 8 O 4   Erythrose, Erythrulose
ketotetroses
Aldopentoses/      C5H10O5      Ribose , Ribulose
ketopentoses
Aldohexoses/       C6H12O6      Glucose, Fructose
ketohesoses




                Erythrose         Ribose   Ribulose
• Monosaccharides also include derivatives of
  above mentioned monosaccharides e.g. amino
  sugars, sugar alcohols, sugar acids and esters of
  sulfuric acid and phosphoric acid
Disaccharides
• Biose
• Formed when two monosaccharides undergo
  a condensation reaction which involves the
  elimination of a small molecule, such as
  water, from the functional groups only




      Sucrose
Oligosaccharides
• Greek word oligos, meaning "a few", and
  sacchar which means "sugar“
• Saccharide polymers containing a small
  number (typically three to ten) of component
  sugars- Monosaccharides
 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 unit
• 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, lignin
• Polysaccharides have a general formula of
  (C6H10O5)n
• Not sweet, hence called non-sugars
CH2OH                             6CH OH                        CH2OH                        CH2OH                           CH2OH
                                             2
                 O                        5      O          H                   O            H               O       H       H                 O        H
H                         H       H                                 H                H
        H                                 H                             H                         H                                  H
        OH       H    1               4 OH            H 1               OH      H                 OH         H                       OH        H
                              O                                 O                        O                               O                              OH
OH                                                    2
                                              3
        H        OH                       H           OH                H       OH                   H       OH                      H         OH
                                                                        amylose



            CH2OH                          6CH OH                       CH2OH                    CH2OH                           CH2OH
                                              2
                     O                     5      O                             O            H           O               H                O        OH
    H                                 H                             H
            H                              H                            H                        H                               H
            OH       H 1          O       4 OH        H 1       O       OH      H        O       OH      H           O           OH       H
    OH                                                                               H                           H                                 H
                              H                        2    H
                                                  3
            H        OH                    H          OH                H       OH               H       OH                      H        OH
                                                                        cellulose


                 Upon acid hydrolysis produce monosaccharides
Significance
• Key role in maintaining energy balance in the
  biosphere
• Building blocks and source of energy
• Used as excipients in pharmaceuticals
  Dusting Powders, disintegrant, mucilage
• Bio-markers
• As Medicine –heparin, glucose, dextran etc.
• Chromatography and electrophoresis
Oxidation of glucose
• Mild oxidizing agents such as bromine water convert
  glucose to gluconic acid, which is single step reaction
• This reaction is used to differentiate sugars having –
  CHO (reducing) group or 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 grams copper sulfate pentahydrate
      dissolved in 1 litre of distilled water
2-Fehling's Solution B
  346 grams potassium sodium tartrate         and
      120 grams sodium hydroxide in 1 litre of
      distilled water
Fructose also give positive test
• Under alkaline conditions fructose is
  converted to glucose and mannose
Tollens' reagent test "silver mirror"
• Tollens' reagent: when silver nitrate solution is
  treated with sodium hydroxide(NaOH) till 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
Carbohydrates Classification and Importance

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Carbohydrates Classification and Importance

  • 2. Introduction • Chemically: Polyhydroxy aldehydes and ketones • Have hydrogen and oxygen in a ratio of water (2:1) Ribose (C5H10O5) and Glucose (C6H12O6)
  • 3. • General formula Cn(H2O)n.Hence, also called hydrates of carbon • Substances which are converted into polyhydroxy aldehydes and ketones after hydrolysis
  • 4. Importance of carbohydrates • Provide major source of energy (4.1C) • Serve also as stored forms of energy as glycogen in liver and muscles • Protein sparing action • Reduce breakdown of fatty acids and preventing ketosis • Involved in biological recognition processes of immunoglobulin
  • 5. Contn’d • Flavoring and Sweetening agents • Dietary fiber (Cellulose) • Important components of brain cells as neuraminic acids, cerebrosides (Glycolipids) and gangliosides • Important component of nucleic acids as pentose sugars - ribose and deoxyribose
  • 6. Contn’d • Function as physiological anticoagulant (Heparin) • Plasma expanders (Dextran) • Parenteral nutrition • Binders in tablets • Disintegrators in tablets • Analytical techniques: Agar agar and starch • Diagnostic markers
  • 7. Classification • Have been classified into 4 main groups – Monosaccharides – Disaccharides – Oligosaccharides – Polysaccharides
  • 8. Monosaccharides • Carbohydrates which can’t further be broken down into simpler units by acid hydrolysis • Classified according to the number of carbon atoms present in them – For example trioses, tetroses and hexoses
  • 9. • 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 groups – i.e aldotriose or ketotriose
  • 10. Aldotrioses/ C3 H 6 O 3 Glyceraldehyde and dihydroxy ketotrioses acetone Aldotetroses/ C4 H 8 O 4 Erythrose, Erythrulose ketotetroses Aldopentoses/ C5H10O5 Ribose , Ribulose ketopentoses Aldohexoses/ C6H12O6 Glucose, Fructose ketohesoses Erythrose Ribose Ribulose
  • 11. • Monosaccharides also include derivatives of above mentioned monosaccharides e.g. amino sugars, sugar alcohols, sugar acids and esters of sulfuric acid and phosphoric acid
  • 12. Disaccharides • Biose • Formed when two monosaccharides undergo a condensation reaction which involves the elimination of a small molecule, such as water, from the functional groups only Sucrose
  • 13. Oligosaccharides • Greek word oligos, meaning "a few", and sacchar which means "sugar“ • Saccharide polymers containing a small number (typically three to ten) of component sugars- Monosaccharides For example Raffinose
  • 14. 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 unit
  • 15. • 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, lignin • Polysaccharides have a general formula of (C6H10O5)n • Not sweet, hence called non-sugars
  • 16. CH2OH 6CH OH CH2OH CH2OH CH2OH 2 O 5 O H O H O H H O H H H H H H H H H H H OH H 1 4 OH H 1 OH H OH H OH H O O O O OH OH 2 3 H OH H OH H OH H OH H OH amylose CH2OH 6CH OH CH2OH CH2OH CH2OH 2 O 5 O O H O H O OH H H H H H H H H OH H 1 O 4 OH H 1 O OH H O OH H O OH H OH H H H H 2 H 3 H OH H OH H OH H OH H OH cellulose Upon acid hydrolysis produce monosaccharides
  • 17. Significance • Key role in maintaining energy balance in the biosphere • Building blocks and source of energy • Used as excipients in pharmaceuticals Dusting Powders, disintegrant, mucilage • Bio-markers • As Medicine –heparin, glucose, dextran etc. • Chromatography and electrophoresis
  • 18. Oxidation of glucose • Mild oxidizing agents such as bromine water convert glucose to gluconic acid, which is single step reaction • This reaction is used to differentiate sugars having – CHO (reducing) group or those yielding such group
  • 19. Example is Fehling's solution test • Fehling's solution is composed of equal parts of two solutions: 1-Fehling's solution A 69.28 grams copper sulfate pentahydrate dissolved in 1 litre of distilled water 2-Fehling's Solution B 346 grams potassium sodium tartrate and 120 grams sodium hydroxide in 1 litre of distilled water
  • 20.
  • 21. Fructose also give positive test • Under alkaline conditions fructose is converted to glucose and mannose
  • 22. Tollens' reagent test "silver mirror" • Tollens' reagent: when silver nitrate solution is treated with sodium hydroxide(NaOH) till 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