1. Chapter 7 Carbohydrates and Glycobiology

2. Chapter 7: Carbohydrates Learning Goals 1.Structures of “boxed” sugars: open chain and ring. 2.Amino-, deoxy-, and acidic sugars. 3.Common polysaccharides (amylose, amylopectin, cellulose, chitin, peptidoglycan). 4.Proteoglycans and glycan-domains…lectins. 5.Lipopolysaccharide. 6.Determination of sugar structure, glycosidic bonds.

3. Trioses

4. Hexose Models

5. Pentose Models

6. Three Carbon Sugars

7. Carbonyl on the End

10. Carbonyl Inner-Carbon

12. Epimers

13. Sugars: Carbonyl + Alcohol  Ring Formation

18. Modified Sugars

20. Basis of Fehling’s Reaction = Glucose is Reducing This is the more sensitive and specific test for glucose EOC Problem 15: an exercise in recognizing reducing sugars.

21. Formation of Glycosidic Bond..Polysaccharides: Written from Non-Reducing to Reducing End

22. How Should This Really Be Drawn?

23. Fructose Turned Upside Down

24. This Glucose Should be Flipped Over

25. Sucralose - Sucrose Comparison Sucralose is 600 times sweeter than Sucrose Pardon the skeletized molecules.. Not showing all the atoms, you could fill them in.

26. What Is Sweet? Tasting Panels: Taste Relative to Sucrose….dilutions of the test molecules. Compound Sweetness Lactose0.16 Glycerol0.60 Glucose0.75 Sucrose1.0 Fructose1.75 Aspartame250 Na-saccharine510 Sucralose600 Lugduname225,000

27. Sweetner’s Calories Because of sucralose intense sweetness, what is sold in the supermarket is mixed with a filler: fluffed glucose or fluffed maltodextrin. (Fluffed by the same process that makes Puffed Wheat or Puffed Rice breakfast cereals). While sucralose can not be metabolized, the filler does have calories.. but less than 5 cal/gram. So the FDA allows the claim that sucralose products have no calories. What is the nutritional calorie compared to the biochemical calorie? What are the safety concerns?

30. Storage Polysaccharides EOC Problem 20: How long can a game bird fly using its muscle glycogen? To solve this assume you have 1 gram of muscle tissue.

31. Glycogen and Starch…almost all α 1,4 Glycogen and Amylopectin have α 1  6 branches

32. Two cartoons of Amylopectin

33. Cellulose is Beta 1,4 linked When aligned, they form H-bonds and fit like Leggo’s blocks to become insoluble. EOC Problem 17 compares the solubility of glycogen and cellulose: both polymers of glucose, but different.

34. Cellulase is Only produced by Some Fungi and Some Bacteria EOC Problem 19: The growth rate of bamboo, one of the fastest growing cellulose system in the world.

35. Chitin – What are the modifications from cellulose?

36. OMG, Phi, Psy and Omega Angles on 1,6 Linkages

37. Ramachandran Redux

38. Amylose Helix EOC Problem 18 compares the lengths of cellulose and amylose: both polymers of glucose, but different.

39. Agarose

40. Peptidoglycan Has Interpeptide Bridges

43. Syndecan – Human Membrane Core Protein Heparan is the same as Heparin with a few less sulfonates.

44. S-domains have 4 Functions

48. EOC Problem 23 has a good question about how heparin (which is not heparin) binds to antithrombin and demonstrates why clinical plastic and glassware is often coated with heparin.

49. Extracellular Matrix Proteolgycan Atomic Force Microscopy

51. Carbohydrate Linkages to Protein

52. Gram Negative Bacterial Lipopolysaccharide

55. Be sure to do EOC Problem 27..determining branching in a polysaccharide

56. Mass Spectrometry of Oligos attached to a Protein

57. Things to Know and Do Before Class 1.Know the structures of some of the “boxed” sugars. 2.Be able to diagram those with a ring conformation (Haworth projection) and which sugars are epimers of others. 3.Difference between a hemiacetal and a hemiketal. 4.Acetylated, phosphorylated, acidic, deoxy and amino sugars. 5.Making and breaking the glycosidic bond. 6.Fundamental structure of polysaccharides: amylose, amylopectin, cellulose, chitin, peptidoglycan, proteoglycans and lipopolysaccharide. 7.Determination of polysaccharide bonds. 8.EOC Problems 15, 17-20, 23, 27.