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Carbohydrates



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

โ€ข Substances which are converted into
  polyhydroxy aldehydes and ketones
  after hydrolysis
Importance of carbohydrates
โ€ข Provide major source of energy (4.1C)
โ€ข Serve also as stored forms of energy as
  glycogen in liver and muscles
โ€ข Protein sparing action
โ€ข Reduce breakdown of fatty acids and
  preventing ketosis
โ€ข Involved in biological recognition processes of
  immunoglobulin
Contnโ€™d
โ€ข Flavoring and Sweetening agents
โ€ข Dietary fiber (Cellulose)
โ€ข Important components of brain cells as
  neuraminic acids, cerebrosides (Glycolipids)
  and gangliosides
โ€ข Important component of nucleic acids as
  pentose sugars - ribose and deoxyribose
Contnโ€™d
โ€ข Function as physiological anticoagulant
  (Heparin)
โ€ข Plasma expanders (Dextran)
โ€ข Parenteral nutrition
โ€ข Binders in tablets
โ€ข Disintegrators in tablets
โ€ข Analytical techniques: Agar agar and starch
โ€ข Diagnostic markers
Classification
โ€ข Have been classified into 4 main
  groups
  โ€“ Monosaccharides
  โ€“ Disaccharides
  โ€“ Oligosaccharides
  โ€“ Polysaccharides
Monosaccharides
โ€ข Carbohydrates which canโ€™t further be broken down
  into simpler units by acid hydrolysis
โ€ข Classified according to the number of carbon atoms
  present in them
   โ€“ For example trioses, tetroses and hexoses
โ€ข Usually have 3-9 carbon atoms
โ€ข Further sub-classified into aldoses and ketoses
โ€ข Exact name is based on
  โ€“ number of carbons atoms
  โ€“ presence of aldehyde or ketone groups
  โ€“ 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
โ€ข 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
โ€ข Biose
โ€ข 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
โ€ข Greek word oligos, meaning "a few", and
  sacchar which means "sugarโ€œ
โ€ข Saccharide polymers containing a small
  number (typically three to ten) of component
  sugars- Monosaccharides
 For example Raffinose
Polysaccharides
โ€ข Polymeric carbohydrate structures, formed
  by repeating units (either mono- or di-
  saccharides) joined together by glycoside
  bond
โ€ข Such structures are often linear, but may
  contain various degrees of branching
โ€ข Polysaccharides are often quite
  heterogeneous, containing slight
  modifications of the repeating unit
โ€ข 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
โ€ข Polysaccharides have a general formula of
  (C6H10O5)n
โ€ข 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
โ€ข Key role in maintaining energy balance in the
  biosphere
โ€ข Building blocks and source of energy
โ€ข Used as excipients in pharmaceuticals
  ๏ƒ˜Dusting Powders, disintegrant, mucilage
โ€ข Bio-markers
โ€ข As Medicine โ€“heparin, glucose, dextran etc.
โ€ข Chromatography and electrophoresis
Oxidation of glucose
โ€ข Mild oxidizing agents such as bromine water convert
  glucose to gluconic acid, which is single step reaction
โ€ข This reaction is used to differentiate sugars having โ€“
  CHO (reducing) group or those yielding such group
Example is Fehling's solution test
โ€ข 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
โ€ข Under alkaline conditions fructose is
  converted to glucose and mannose
Tollens' reagent test "silver mirror"
โ€ข 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]+
โ€ข The diammine silver complex is an oxidizing
  agent, which is itself reduced to silver metal
Carbohydrate 1

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Carbohydrate 1

  • 2. Introduction โ€ข Chemically: Polyhydroxy aldehydes and ketones โ€ข Have hydrogen and oxygen in a ratio of water (2:1) Ribose (C5H10O5) and Glucose (C6H12O6)
  • 3. โ€ข General formula Cn(H2O)n.Hence, also called hydrates of carbon โ€ข Substances which are converted into polyhydroxy aldehydes and ketones after hydrolysis
  • 4. Importance of carbohydrates โ€ข Provide major source of energy (4.1C) โ€ข Serve also as stored forms of energy as glycogen in liver and muscles โ€ข Protein sparing action โ€ข Reduce breakdown of fatty acids and preventing ketosis โ€ข Involved in biological recognition processes of immunoglobulin
  • 5. Contnโ€™d โ€ข Flavoring and Sweetening agents โ€ข Dietary fiber (Cellulose) โ€ข Important components of brain cells as neuraminic acids, cerebrosides (Glycolipids) and gangliosides โ€ข Important component of nucleic acids as pentose sugars - ribose and deoxyribose
  • 6. Contnโ€™d โ€ข Function as physiological anticoagulant (Heparin) โ€ข Plasma expanders (Dextran) โ€ข Parenteral nutrition โ€ข Binders in tablets โ€ข Disintegrators in tablets โ€ข Analytical techniques: Agar agar and starch โ€ข Diagnostic markers
  • 7. Classification โ€ข Have been classified into 4 main groups โ€“ Monosaccharides โ€“ Disaccharides โ€“ Oligosaccharides โ€“ Polysaccharides
  • 8. Monosaccharides โ€ข Carbohydrates which canโ€™t further be broken down into simpler units by acid hydrolysis โ€ข Classified according to the number of carbon atoms present in them โ€“ For example trioses, tetroses and hexoses
  • 9. โ€ข Usually have 3-9 carbon atoms โ€ข Further sub-classified into aldoses and ketoses โ€ข Exact name is based on โ€“ number of carbons atoms โ€“ presence of aldehyde or ketone groups โ€“ 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. โ€ข 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 โ€ข Biose โ€ข 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 โ€ข Greek word oligos, meaning "a few", and sacchar which means "sugarโ€œ โ€ข Saccharide polymers containing a small number (typically three to ten) of component sugars- Monosaccharides For example Raffinose
  • 14. Polysaccharides โ€ข Polymeric carbohydrate structures, formed by repeating units (either mono- or di- saccharides) joined together by glycoside bond โ€ข Such structures are often linear, but may contain various degrees of branching โ€ข Polysaccharides are often quite heterogeneous, containing slight modifications of the repeating unit
  • 15. โ€ข 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 โ€ข Polysaccharides have a general formula of (C6H10O5)n โ€ข 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 โ€ข Key role in maintaining energy balance in the biosphere โ€ข Building blocks and source of energy โ€ข Used as excipients in pharmaceuticals ๏ƒ˜Dusting Powders, disintegrant, mucilage โ€ข Bio-markers โ€ข As Medicine โ€“heparin, glucose, dextran etc. โ€ข Chromatography and electrophoresis
  • 18. Oxidation of glucose โ€ข Mild oxidizing agents such as bromine water convert glucose to gluconic acid, which is single step reaction โ€ข This reaction is used to differentiate sugars having โ€“ CHO (reducing) group or those yielding such group
  • 19. Example is Fehling's solution test โ€ข 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 โ€ข Under alkaline conditions fructose is converted to glucose and mannose
  • 22. Tollens' reagent test "silver mirror" โ€ข 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]+ โ€ข The diammine silver complex is an oxidizing agent, which is itself reduced to silver metal