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Macromolecules & Carbohydrates

Macromolecules & Carbohydrates. Lecture 3 Dr. Mamoun Ahram. Cell's weight. Subunits. Subunits: the small building blocks (precursors) used to make macromolecules Macromolecules: large molecules made of subunits . Macromolecules. Carbohydrates (monosaccharides) Proteins (amino acids)

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Macromolecules & Carbohydrates

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  1. Macromolecules& Carbohydrates Lecture 3 Dr. Mamoun Ahram

  2. Cell's weight

  3. Subunits • Subunits: the small building blocks (precursors) used to make macromolecules • Macromolecules: large molecules made of subunits

  4. Macromolecules • Carbohydrates (monosaccharides) • Proteins (amino acids) • Nucleic acids (nucleotides) • Lipids (fatty acids) • Except for lipids, these macromolecules are also considered polymers

  5. Relationship (monomers and polymers)

  6. How water is removed? • Mechanism 1: One subunit contributes an “H” and the other subunit contributes an “OH” • Mechanism 2: One subunit contributes 2 “H” the other subunit contributes an “O”

  7. Carbohydrates

  8. What are they? • Carbohydrates are polyhydroxy aldehydes or ketones • Saccharide is another name for a carbohydrate

  9. Functions • Source of energy • Structure (cellulose and chitin) • Building blocks • Cellular recognition

  10. Classification I • Monosaccharides • Disaccharides • Oligosaccharides • Polysaccharides

  11. Monosaccharides • Basic chemical formula: (CH2O)n • They contain two or more hydroxyl groups

  12. Drawing sugars • Fisher projections or perspective structural formulas Forward Backward Top (C1): Most highly oxidized C

  13. Numbering carbons…again

  14. Classification 2 • By the number of carbon atoms they contain

  15. Trioses

  16. Glyceraldehyde Chiral carbon

  17. Mirror images and non-superimposable, then…stereoisomers

  18. Stereoisomers

  19. This is different than structural isomers

  20. Sugar enantiomers (D- vs. L-)

  21. Which chiral carbon?

  22. Number of possible stereoisomers • 2n (n is the number of chiral carbons in a sugar molecule)

  23. Isomers of glucose

  24. Diastereomers

  25. Epimers

  26. Formation of a ring structure

  27. Hemiacetal vs. hemiketal

  28. Haworth vs. Fischer projections

  29. Ring structures

  30. Example

  31. Anomers

  32. - vs. -glucopyranose

  33. Cyclic fructose

  34. Galactose

  35. Fischer vs. HaworthLeft-right vs. up-down

  36. Cyclic aldohexoses

  37. Cyclic ribofuranose

  38. Modified sugars

  39. Sugar esters (esterification) • What is the reacting functional group? Where does it react? What are the end products? Where are they used?

  40. Sugar acids (oxidation) • Where is it oxidized? What does it form?

  41. Example 1

  42. Example 2

  43. Example 3

  44. Note • Oxidation of ketoses to carboxylic acids does not occur

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