1 / 145

Modified Chapter 25 Carbohydrates

Modified Chapter 25 Carbohydrates. 25.1 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.

page
Download Presentation

Modified Chapter 25 Carbohydrates

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript


  1. ModifiedChapter 25Carbohydrates

  2. 25.1Classification 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 25.1 Some Classes of Carbohydrates • No. of carbons AldoseKetose • 4 AldotetroseKetotetrose • 5 AldopentoseKetopentose • 6 AldohexoseKetopentose • 7 AldoheptoseKetoheptose • 8 AldooctoseKetooctose

  8. 25.2Fischer Projections and D-L Notation

  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. 25.3The 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 O CH O H OH HO H H OH HO H 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 O CH O HO H H HO HO H H OH CH2OH CH2OH The Four Aldotetroses • L-Erythrose and D-threose are diastereomers L-Erythrose D-Threose

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

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

  21. 25.4Aldopentoses 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 25.5.

  25. 25.5A 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 OH H 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 OH H OH H CH2OH The Eight D-Aldohexoses • Allose • Altrose • Glucose • Mannose • Gulose • Idose • Galactose • Talose

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

  50. CH O CH O OH HO H H HO OH H H OH H H HO HO OH H 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

More Related