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Carbohydrates

Carbohydrates. CH339K. What Makes a Carbo a Carbo?. Overall formula. Where n ≥ 3. Etymology:   From their general formula C n (H 2 O) n ; they were once thought to be hydrates of carbon. . Simplest Carbos: N=3 2 Tautomers.

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Carbohydrates

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  1. Carbohydrates CH339K

  2. What Makes a Carbo a Carbo? Overall formula Where n ≥ 3 Etymology:  From their general formula Cn(H2O)n; they were once thought to be hydrates of carbon.

  3. Simplest Carbos: N=32 Tautomers Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. (Wikipedia)

  4. Vertical bonds go into the plane of the projection Horizontal bonds emerge from the plane of projection Glyceraldehyde exists as a pair of enantiomers Enantiomers are non-superimposable mirror images

  5. R-S Nomenclature (for the Organic guys)

  6. With n > 3, you can form diastereomers Diastereomers are stereoisomers that are not mirror images

  7. Hemiacetals and Hemiketals An aldehyde or a ketone can react wth an alcohol

  8. Ring formation

  9. Ring formation in a ketose

  10. AnomersDiffer at the hemiacetal or hemiketal carbon a-D-Glucose b-D-Glucose

  11. Furanoses and Pyranoses

  12. Multiple possible rings in a C6-Ketose

  13. Multiple Possible Rings in a C5-Aldose

  14. Ring pucker

  15. Epimers Differ at only one carbon, but not the anomeric carbon

  16. Sugar Derivatives +H2O -2H+,e- aldonolactone Aldonic acid Cu2+ +NH3, -H2O Acetic anhydride Amino sugar Alduronic acid Substituted Amino sugar

  17. Sugar Derivatives

  18. Glycosides Glycoside: Any of a group of organic compounds that yield a sugar and one or more nonsugar substances on hydrolysis.

  19. Natural Glycosides Amygdalin is a poison found in the seeds of bitter almonds. It releases cyanide upon hydrolysis.

  20. Amygdalin is also known as Laetrile or “Vitamin B17,” a quack (excuse me, “alternative”) cancer treatment.

  21. Natural Glycosides Digitoxin is used as a heart stimulant in medicine; related componds are used as poisons in murder mysteries

  22. Polymerization

  23. Activation – couple to UDP

  24. Disaccharides

  25. Storage Polysacharides

  26. amylopectin

  27. Amylose Structure

  28. Iodine Test for Starch – Molecular Basis I2 + I- I3

  29. Amylopectin: a-1,4 + a-1,6

  30. Glycogen : a-1,4 + a-1,6 Glycogen in liver cells – stained with carmin

  31. Storage Polysaccharides

  32. Structural Polysaccharides

  33. Cellulose

  34. Cellulose complexes • β(1-4) linkages form flat sheets • analogous to β-sheets in proteins • multiple hydrogen bonds between strands.

  35. Chitin

  36. Insect cuticles

  37. Self-Nonself Recognition – Blood Groups

  38. Bacterial Cell Walls Gram + Gram - Staphylococcus aureus Escherischia coli

  39. Bacterial Cell Walls Gram - Gram +

  40. Bacterial Cell Walls – another view

  41. Peptidoglycan Components E. coli S. aureus

  42. What the heck is diaminopimelate? Lysine with an extra carboxyl attached to Ce.

  43. Transpeptidase cross-links the individual chains Gram - Gram +

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