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Introduction carbohydrates
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Introduction carbohydrates

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Transcript

  • 1. Carbohydrates
  • 2. Carbohydrates  Most abundant class of biological molecules on Earth  Originally produced through CO2 fixation during photosynthesis
  • 3. Roles of Carbohydrates  Energy storage (glycogen,starch)  Structural  Cellular components (cellulose,chitin) recognition  Carbohydrate derivatives include DNA, RNA, co- factors, glycoproteins, glycolipids
  • 4. Carbohydrates  Monosaccharides (simple sugars) cannot be broken down into simpler sugars under mild conditions  Oligosaccharides  Polysaccharides = "a few" - usually 2 to 10 are polymers of the simple sugars
  • 5. Monosaccharides  Polyhydroxy ketones (ketoses) and aldehydes (aldoses)  Aldoses and ketoses contain aldehyde and ketone functions, respectively
  • 6.  Ketose named for “equivalent aldose” + “ul” inserted  Triose, tetrose, etc. denotes number of carbons  Empirical formula = (CH2O)n
  • 7. Monosaccharides are chiral  Aldoses with 3C or more and ketoses with 4C or more are chiral  The number of chiral carbons present in a ketose is always one less than the number found in the same length aldose  Number of possible steroisomers = 2n (n = the number of chiral carbons)
  • 8. Stereochemistry
  • 9.  Enantiomers  Pairs = mirror images of isomers that have opposite configurations at one or more chiral centers but are NOT mirror images are diastereomers  Epimers = Two sugars that differ in configuration at only one chiral center
  • 10. Cyclization of aldose and ketoses introduces additional chiral center  Aldose sugars (glucose) can cyclize to form a cyclic hemiacetal
  • 11. •Ketose sugars (fructose) can cyclize to form a cyclic hemiketal
  • 12. Haworth Projections O H -OH up = beta -OH down = alpha C1 H C2 OH HO C3 H H C4 OH H C5 OH CH2OH 6 5 4 1 3 2 Anomeric carbon (most oxidized) For all non-anomeric carbons, -OH groups point down in Haworth projections if pointing right in Fischer projections
  • 13. Monosaccharides can cyclize to form Pyranose / Furanose forms a = 64% b = 36% a = 21.5% b = 58.5% a = 13.5% b = 6.5%
  • 14. Conformation of Monosaccharides Pyranose sugars not planar molecules, prefer to be in either of the two chair conformations.
  • 15. Reducing Sugars  When in the uncyclized form, monosaccharides act as reducing agents.  Free carbonyl group from aldoses or ketoses can reduce Cu2+ and Ag+ ions to insoluble products
  • 16. Derivatives of Monosaccharides
  • 17. Sugar Phosphates
  • 18. Deoxy Acids
  • 19. Amino Sugars
  • 20. Sugar alcohols
  • 21. Monosaccharide structures you need to know  Glucose  Fructose  Ribulose  Glyceraldehyde  Dihydroxyacetone