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  1. 1. Dr. Daxaben N. Mehta Principal Smt. Sadguna C.U.Shah Home Science and C. U. Shah Arts & Commerce Mahila College, Wadhwancity, Dist: Surendranagar Home Science Carbohydrates
  2. 2. Term carbohydrate is derived from the French: hydrate de carbone compounds composed of C, H, and O (CH2O)n when n = 5 then C5H10O5 not all carbohydrates have this empirical formula: deoxysugars, aminosugars carbohydrates are the most abundant compounds found in nature (cellulose: 100 billion tons annually) Home Science Carbohydrates
  3. 3. • Most carbohydrates are found naturally in bound form rather than as simple sugars • Polysaccharides (starch, cellulose, inulin, gums) • Glycoproteins and proteoglycans (hormones, blood group substances, antibodies) • Glycolipids (cerebrosides, gangliosides) • Glycosides • Mucopolysaccharides (hyaluronic acid) • Nucleic acids Home Science Carbohydrates
  4. 4. • sources of energy • intermediates in the biosynthesis of other basic biochemical entities (fats and proteins) • associated with other entities such as glycosides, vitamins and antibiotics) • form structural tissues in plants and in microorganisms (cellulose, lignin, murein) • participate in biological transport, cell-cell recognition, activation of growth factors, modulation of the immune system Home Science Carbohydrates
  5. 5. • Monosaccharides (monoses or glycoses) • Trioses, tetroses, pentoses, hexoses • Oligosaccharides • Di, tri, tetra, penta, up to 9 or 10 • Most important are the disaccharides • Polysaccharides or glycans • Homo and Heteropolysaccharides • Complex carbohydrates Home Science Carbohydrates
  6. 6. • also known as simple sugars • classified by 1. the number of carbons and 2. whether aldoses or ketoses • most (99%) are straight chain compounds • D-glyceraldehyde is the simplest of the aldoses (aldotriose) • all other sugars have the ending ose (glucose, galactose, ribose, lactose, etc…) Home Science Carbohydrates
  7. 7. • Differences in structures of sugars are responsible for variations in properties • Physical Crystalline form; solubility; rotatory power • Chemical Reactions oxidations, reductions, condensations • Physiological Nutritive value (human, bacterial); sweetness; absorption Home Science Carbohydrates
  8. 8. Home Science Carbohydrates
  9. 9. H C (H O C OH)n CH 2 OH Aldose C H H H H C OH C H C OH CH 2 OH H C OH Aldotriose n=1 C O H C OH H C H C O O CH 2 OH Aldotetrose n=2 H C O H C OH OH H C OH OH H C OH H C OH CH 2 OH Aldopentose n=3 CH 2 OH Aldohexose n=4 Home Science Carbohydrates
  10. 10. CH 2 OH C CH 2 OH O C (H C CH 2 OH CH 2 OH Ketose C O OH)n CH 2 OH CH 2 OH H C OH C O CH 2 OH H C OH C O H C OH C OH O CH 2 OH Ketotriose Ketotetrose n=0 n=1 H CH 2 OH H Ketopentose H OH C OH n=2 CH 2 OH Ketohexose n=3 Home Science Carbohydrates
  11. 11. H H H H C O O H C OH H C OH C O HO C H OH C H H HO C H OH C H C OH HO C H CH 2 OH C OH C OH O HO C H HO C H H C C CH 2 OH H these two aldotetroses are enantiomers. They are stereoisomers that are mirror images of each other CH 2 OH CH 2 OH these two aldohexoses are C-4 epimers. they differ only in the position of the hydroxyl group on one asymmetric carbon (carbon 4) Home Science Carbohydrates
  12. 12. • Pairs of stereoisomers • Designated by D- or L- at the start of the name. • They are mirror images that can’t be overlapped. Home Science Carbohydrates
  13. 13. Home Science Carbohydrates
  14. 14. CH O CHO HO H H OH C C C H2 O H C H2 O H CHO CHO HO H C H2 O H Home Science H OH C H2 O H Carbohydrates
  15. 15. Home Science Carbohydrates
  16. 16. ald o tetro s es 1 CHO 1CHO high est n u m b ered "chira l" ca rb on 2 H 3 H OH OH HO HO h ig h est n um b ered "chira l" ca rb on H H OH C H 2O H D -th reose Home Science high est nu m b e red "chira l" ca rb o n H L -erythrose CHO CHO HO 3 H 4 C H 2O H 4 CH OH 2 D -erythro se 2 H HO OH H high est n u m b ered "chira l" ca rb on C H 2O H L-thre ose Carbohydrates
  17. 17. C5, three chiral carbons, eight stereoisomers CHO H H OH HO H OH H OH HO H OH H OH H C H 2O H D -ribose H C H 2O H D -arabinose Home Science CHO CHO CHO OH HO H H HO H OH C H 2O H D -xylose Carbohydrates H OH C H 2O H D -lyxose
  18. 18. four chiral carbons, sixteen stereoisomers CHO CHO CHO CHO CHO CHO CHO CHO H OH HO H H OH HO H H OH HO H H OH HO H H OH H OH HO H HO H H OH H OH HO H HO H H OH H OH H OH H OH HO H HO H HO H HO H H OH H OH H OH H OH H OH H OH H OH H OH CH 2 OH D-allose CH 2 OH CH 2 OH CH 2 OH D-altrose D- glucose D-mannose Home Science CH 2 OH D-gulose CH 2 OH D-idose Carbohydrates CH 2 OH CH 2 OH D-galactose D-talose
  19. 19. Home Science Carbohydrates
  20. 20. CH 2 O H CH 2 O H CH 2 OH O CH 2 OH hydroxyacetone CH 2 O H CH 2 O H O O O H OH H H OH HO CH 2 O H OH HO H H H OH CH 2 O H H OH CH 2 OH D-ribulose Home Science Dxylulose D-fructose Carbohydrates O HO H H OH H OH H OH CH 2 O H D-sedohepuloase
  21. 21. Home Science Carbohydrates
  22. 22. • Fisher projection: straight chain representation • Haworth projection: simple ring in perspective • Conformational representation: chair and boat configurations Home Science Carbohydrates
  23. 23. • draw either a six or 5-membered ring including oxygen as one atom • most aldohexoses are six-membered • aldotetroses, aldopentoses, ketohexoses are 5-membered O Home Science O Carbohydrates
  24. 24. • next number the ring clockwise starting next to the oxygen 5 O O 1 4 3 2 1 4 3 2 • if the substituent is to the right in the Fisher projection, it will be drawn down in the Haworth projection (Down-Right Rule) Home Science Carbohydrates
  25. 25. • for D-sugars the highest numbered carbon (furthest from the carbonyl) is drawn up. For L-sugars, it is drawn down • for D-sugars, the OH group at the anomeric position is drawn down for and up for β. For L-sugars is up and β is down Home Science Carbohydrates
  26. 26. D-glucose can cyclize in two ways forming either furanose or pyranose structures Home Science Carbohydrates
  27. 27. 6 CH 2 O H 5 OH H 1 H HO H HOH 2 C 2 HO OH 3 4 5 H OH H H OH 2 C H O H H HO 5 4 3 H OH H 2 CHO 6 CH 5 4 D-glucose HO OH H 1 H 3 H OH 3 H 6 H H H OH H HO Home Science O H OH 4 2O H H OH 5 OH new chiral center 1 OH 6 H CH 2 OH OH H 6 1 2 3 H O H OH H 4 CHO 6 1 2 O 4 CH 2 O H 5 O H OH HO 3 H OH Carbohydrates H H 1 2 OH OH
  28. 28. : Glucose exists in aqueous solution primarily in the six-membered, pyranose ring form • Results from intramolecular nucleophilic addition of the –OH group at C5 to the C1 carbonyl group Home Science Carbohydrates
  29. 29. : • The name pyranose is derived from pyran Pyran is the name of the unsaturated sixmembered cyclic ether • Pyranose rings have chairlike geometry with axial and equatorial substituents Home Science Carbohydrates
  30. 30. The two diastereomers are called anomers and the hemiacetal carbon atom is referred to as the anomeric center Home Science Carbohydrates
  31. 31. D-ribose and other five-carbon saccharides can form either furanose or pyranose structures Home Science Carbohydrates
  32. 32. H 5 OH H CHO H H H H 2 3 4 5 H HO H 5 2 4 3 H 5 4 O OH H H H HO 1 H 3 OH OH HO H H H 1 2 3 OH OH H HO OH H O H H 4 1 H OH new chiral center 1 CHO H H O H OH OH 5 OH H OH 4 D-ribose H H HO 3 HO Home Science H H H 1 H 2 O 4 HO 5 O H H H 3 OH OH Carbohydrates H 1 2 OH OH
  33. 33. 1 6 C H 2O H 2 HO H H O H 2C O 3 H 4 6 H O H 2C HO H OH 5 4 H O H 2C 1 2 3 C H 2O H 3 H 2 H OH H C H 2O H HO 4 2 C H 2O H 3 H OH 1 OH O H 5 HO 4 H C H 2O H O OH H 5 O H OH H OH 5 6 1 6 OH 1 H C H 2O H 2 HO H H 6 O 3 4 5 H OH H 6 H O H 2C 5 4 3 OH OH H OH C H 2O H 2 O 1 C H 2O H 5 H Home Science H O H HO 2 HO 3 4 HO 6 OH H H OH 6 H C H 2O H 1 Carbohydrates 4 H 5 O H HO H HO OH C H 2O H 3 OH 2 H 1
  34. 34. Chair and boat conformations of a pyranose sugar 2 possible chair conformations of Home Science -D-glucose Carbohydrates
  35. 35. • A property exhibited by any compound whose mirror images are non-superimposable • Asymmetric compounds rotate plane polarized light Home Science Carbohydrates
  36. 36. Measurement of optical activity in chiral or asymmetric molecules using plane polarized light Molecules may be chiral because of certain atoms or because of chiral axes or chiral planes Measurement uses an instrument called a polarimeter (Lippich type) Rotation is either (+) dextrorotatory or (-) levorotatory Home Science Carbohydrates
  37. 37. Home Science Carbohydrates
  38. 38. Home Science Carbohydrates
  39. 39. Magnitude of rotation depends upon: Nature of the compound Length of the tube usually expressed in decimeters Wavelength of the light source employed Temperature of sample Concentration of analyte in grams per 100 ml Home Science Carbohydrates
  40. 40. • • • • • • D-glucose D-galactose D-mannose D-xylose Sucrose Invert sugar +52.7 +80.2 +14.2 +18.8 +66.5 -19.8 Home Science D-fructose L-arabinose D-arabinose Lactose Maltose Dextrin Carbohydrates -92.4 +104.5 -105.0 +55.4 +130.4 +195
  41. 41. • Carbonyl reactions: • Osazone formation • Reduction , Oxidation • Amino Sugars Home Science Carbohydrates
  42. 42. • consists of reacting the monosaccharide with phenylhydrazine • D-fructose and D-mannose give the same osazone as D-glucose • seldom used for identification; we now use HPLC or mass spectrometry Home Science Carbohydrates
  43. 43. The aldehyde group of an aldose react with phenylhydrazine. O H CH C NNHC 6 H 5 + 3C 6 H 5 N HN H 2 (C HOH)n C NNHC 6 H 5 C H 2 OH + C 6 H 5 N H 2 + NH 3 + H 2 O (CHOH)n CH 2 OH phenylosazone (±½ëÛ) Home Science Carbohydrates
  44. 44. • Aldoses may be oxidized to 3 types of acids Aldonic acids: aldehyde group is converted to a carboxyl group Uronic acids: aldehyde is left intact and primary alcohol at the other end is oxidized to COOH Saccharic acids (glycaric acids) – oxidation at both ends of monosaccharide) Home Science Carbohydrates
  45. 45. • Br2 is a mild oxidant that gives good yields of aldonic acid products Home Science Carbohydrates
  46. 46. • Aldoses are oxidized in warm, dilute HNO3 to dicarboxylic acids called aldaric acids Home Science Carbohydrates
  47. 47. • Enzymatic oxidation at the –CH2OH end of aldoses yields uronic acids Home Science Carbohydrates
  48. 48. • • • • • either done catalytically or enzymatically Forms sugar alcohol (alditol) glucose form sorbitol (glucitol) mannose forms mannitol fructose forms a mixture of mannitol and sorbitol • glyceraldehyde gives glycerol Home Science Carbohydrates
  49. 49. Aldoses( and ketoses) can be reduced with sodium borohydride CH O H O H 2C HO HO H O HO CH 2 O H OH H HO H N aBH 4 HO OH H H H OH H OH OH OH H OH CH 2 O H CH 2 O H D -G lucitol D -G lucose Home Science (D -ÆÏÌÑ ÌÇ ´¼ £© Carbohydrates
  50. 50. Home Science Carbohydrates
  51. 51. • These are monosaccharides which lack one or more hydroxyl groups on the molecule • one quite ubiquitous deoxy sugar is 2’deoxy ribose which is the sugar found in DNA • 6-deoxy-L-mannose (L-rhamnose) is used as a fermentative reagent in bacteriology Home Science Carbohydrates
  52. 52. examples of deoxysugars Home Science Carbohydrates
  53. 53. Several sugar esters important in metabolism Home Science Carbohydrates
  54. 54. Home Science Carbohydrates
  55. 55. Home Science Carbohydrates
  56. 56. • Most common are the disaccharides • Sucrose, lactose, and maltose • Maltose hydrolyzes to 2 molecules of Dglucose • Lactose hydrolyzes to a molecule of glucose and a molecule of galactose • Sucrose hydrolyzes to a moledule of glucose and a molecule of fructose Home Science Carbohydrates
  57. 57. • Malt sugar. Not common in nature except in germinating grains. α (1 CH 2 OH CH 2 OH H O H OH 4) linkage. H H H O O OH H OH H H OH H OH -D-glucose Home Science OH H -D-glucose Carbohydrates
  58. 58. • Milk sugar - dimer of -D-galactose and D-glucose. (1 4) O H H OH O H O H OH OH -D-galactose Home Science OH H H H H H - CH 2 OH CH 2 OH OH or H OH -D-glucose Carbohydrates
  59. 59. CH 2 OH • Table sugar - most H common sugar in all H OH plants. • Sugar cane and beet, OH H are up to 20% by mass sucrose. CH 2 OH • Disaccharide of H -glucose and H -fructose. (1 2) linkage Home Science O H H OH O O OH Carbohydrates OH CH 2 OH H
  60. 60. • homoglycans (starch, cellulose, glycogen, inulin) • heteroglycans (gums, mucopolysaccharides) Home Science Carbohydrates
  61. 61. • most common storage polysaccharide in plants • composed of 10 – 30% amylose and 70-90% amylopectin depending on the source • the chains are of varying length, having molecular weights from several thousands to half a million Home Science Carbohydrates
  62. 62. • Branched structure due to crosslinks. O H H OH H O H H OH H H H O H H OH β(1 H OH H CHOH H 2 OH H O H H OH H OH O H H O CHOH H 2 OH H O H H OH H OH CH 2 OH H H OH H OH Carbohydrates H H O O 6) link age at crosslink Home Science O H H O H H O O H H O CHOH H 2 OH O H H OH O H CHOH 2 CHOH 2 CHOH 2 CHOH 2 H OH
  63. 63. • Main sources of starch are rice, corn, wheat, potatoes and cassava • Starch is used as an excipient, a binder in medications to aid the formation of tablets. • Industrially it has many applications such as adhesives, paper making, biofuel, textiles Home Science Carbohydrates
  64. 64. • Energy storage of animals. • Stored in liver and muscles as granules. • Similar to amylopectin. α(1 6) linkage O O O O c O O O c O O O O O O O Home Science Carbohydrates
  65. 65. Amylose and amylopectin are the 2 forms of starch. Amylopectin is a highly branched structure, with branches occurring every 12 to 30 residues Home Science Carbohydrates
  66. 66. • These materials provide a thin, viscous, jelly-like coating to cells. The most abundant form is hyaluronic acid. CH 2 OH O H O H COO H CH 2 OH O H O H (1 • 3) COO H CH 2 OH (1 4) O H • COO H O O HO NH C O H H H H H H CH 3 OH H NH OH CH 3 Alternating units of N-acetylglucosamine and D-glucuronic acid. CH 3 OH Home Science NH C O C O H H H H OH - HO O H O O H H H OH - O O HO H OH - Carbohydrates
  67. 67. • Bacterial cell walls are composed primarily of an unbranched polymer of alternating units of Nacetylglucosamine and N-acetylmuramic acid. CH 2 OH CH O H H OH O H H O O 2 OH H OR O H H H H H NH C CH O 3 NH C CH O 3 • Peptide crosslinks between the polymer strands provide extra strength varies based on bacterium. Home Science Carbohydrates
  68. 68. John E McMurry : Organic Chemistry Garrett & Grisham: Textbook of Biochemistry Lehninger: Fundamentals of Biochemistry Morris Hein, Scott Pattison, and Susan Arena: Introduction to Biochemistry Home Science Carbohydrates
  69. 69. Home Science Carbohydrates