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Chapter 23 Carbohydrates

Chapter 23 Carbohydrates. 23.1 Classification of Carbohydrates. Classification of Carbohydrates. Monosaccharide Disaccharide Oligosaccharide Polysaccharide. Monosaccharide. Is not cleaved to a simpler carbohydrate on hydrolysis. Glucose, for example, is a monosaccharide.

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Chapter 23 Carbohydrates

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  1. Chapter 23Carbohydrates

  2. 23.1Classification of Carbohydrates

  3. Classification of Carbohydrates • Monosaccharide • Disaccharide • Oligosaccharide • Polysaccharide

  4. Monosaccharide • Is not cleaved to a simpler carbohydrate on hydrolysis. • Glucose, for example, is a monosaccharide.

  5. C6H12O6+C6H12O6 glucose(a monosaccharide) fructose(a monosaccharide) Disaccharide • Is cleaved to two monosaccharides on hydrolysis. • These two monosaccharides may be the same or different. C12H22O11 + H2O sucrose(a disaccharide)

  6. Higher Saccharides • Oligosaccharide: • Gives two or more monosaccharide units on hydrolysis. Is homogeneous—all molecules of a particular oligosaccharide are the same, including chain length. • Polysaccharide: • Yields "many" monosaccharide units on hydrolysis. Mixtures of the same polysaccharide differing only in chain length.

  7. Table 23.1 Some Classes of Carbohydrates • No. of carbons Aldose Ketose • 4 Aldotetrose Ketotetrose • 5 Aldopentose Ketopentose • 6 Aldohexose Ketohexose • 7 Aldoheptose Ketoheptose • 8 Aldooctose Ketooctose

  8. 23.2Fischer Projections and D,LNotation

  9. Fischer Projections

  10. Fischer Projections

  11. Fischer Projections of Enantiomers

  12. CH O CH O H OH HO H D L CH2OH CH2OH Enantiomers of Glyceraldehyde (+)-Glyceraldehyde (–)-Glyceraldehyde

  13. 23.3The Aldotetroses

  14. CH O H OH H OH D CH2OH An Aldotetrose 1 • Stereochemistry assigned on basis of whetherconfiguration of highest-numbered stereogenic centeris analogous to D or L-glyceraldehyde. 2 3 4

  15. CH O H OH H OH CH2OH An Aldotetrose 1 2 3 4 D-Erythrose

  16. CH CH O O HO H OH H HO H H OH CH2OH CH2OH The Four Aldotetroses • D-Erythrose and L-erythrose are enantiomers. D-Erythrose L-Erythrose

  17. CH O CH O H OH H HO H OH H OH CH2OH CH2OH The Four Aldotetroses • D-Erythrose and D-threose are diastereomers. D-Erythrose D-Threose

  18. CH CH O O H H HO HO HO H H OH CH2OH CH2OH The Four Aldotetroses • L-Erythrose and D-threose are diastereomers. L-Erythrose D-Threose

  19. CH CH O O OH H HO H H H OH CH2OH CH2OH The Four Aldotetroses • D-Threose and L-threose are enantiomers. HO L-Threose D-Threose

  20. CH O CH CH CH O O O H OH H H OH HO HO H H OH HO H H H OH CH2OH CH2OH CH2OH CH2OH The Four Aldotetroses HO D-Erythrose L-Erythrose D-Threose L-Threose

  21. 23.4Aldopentoses and Aldohexoses

  22. The Aldopentoses • There are 8 aldopentoses. • Four belong to the D-series; four belong to the L-series. • Their names are ribose, arabinose, xylose, and lyxose.

  23. CH O CH O CH O CH O OH HO H OH HO H H H OH OH HO H H HO H H OH OH OH OH H H H H CH2OH CH2OH CH2OH CH2OH The Four D-Aldopentoses D-Ribose D-Arabinose D-Xylose D-Lyxose

  24. Aldohexoses • There are 16 aldopentoses. • 8 belong to the D-series; 8 belong to the L-series. • Their names and configurations are best remembered with the aid of the mnemonic described in Section 23.5.

  25. 23.5A Mnemonic for Carbohydrate Configurations

  26. CH O OH H CH2OH The Eight D-Aldohexoses

  27. CH O OH H CH2OH The Eight D-Aldohexoses • All • Altruists • Gladly • Make • Gum • In • Gallon • Tanks

  28. CH O OH H CH2OH The Eight D-Aldohexoses • All Allose • Altruists Altrose • Gladly Glucose • Make Mannose • Gum Gulose • In Idose • Gallon Galactose • Tanks Talose

  29. CH O OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  30. CH O H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  31. CH O HO H OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  32. CH O H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  33. CH O H OH H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  34. CH O HO H H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  35. CH O H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  36. CH O H OH H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  37. CH O H HO H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  38. CH O H OH H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  39. CH O H OH H OH H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  40. CH O HO H H OH H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  41. CH O HO H H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  42. CH O H OH HO H H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  43. CH O H HO HO H H OH OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  44. CH O H OH H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  45. CH O H OH H OH H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  46. CH O HO H H OH H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  47. CH O H HO H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  48. CH O H OH H HO H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  49. CH O HO H H HO H HO OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

  50. CH O CH O HO H H OH OH H HO H H HO H OH HO H OH H CH2OH CH2OH L-Aldohexoses • There are 8 aldohexoses of the L-series. • They have the same name as their mirror image except the prefix is L- rather than D-. D-(+)-Glucose L-(–)-Glucose

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