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Exploring Carbohydrates: Structures, Forms, and Reactions

Dive into carbohydrates with lectures on Fischer projections, cyclic forms, mutarotation, glycosides, disaccharides, and more. Learn about simple monosaccharides, aldohexoses, and complex polysaccharides in detail. Discover the nuances of blood group antigens and synthetic vaccines. Join the fascinating journey of understanding carbohydrates in biochemistry.

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Exploring Carbohydrates: Structures, Forms, and Reactions

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  1. Lecture 37 – Chapter 25 : Carbohydrates • Fischer projections • Cyclic forms – hemiacetal formation, 6 vs. 5 • Mutarotation • Glycosides – formation and examples • Disaccharides • Oligosaccharides and Polysaccharides • Miscellaneous reactions

  2. Simple monosaccharides – Fischer depictions D-glucose D-galactose D-glucosamine N-acetyl-D-glucosamine D-FucNAc D-ManAcA D-Ribose 2-Deoxy-D-ribose

  3. Aldohexoses – cyclic forms and their interconversion All present in solution, free sugars can interconvert

  4. Mutarotation • dissolve dextrose in water, measure [a]D : +112.2 • dissolve b-D-glucopyranose in water, measure [a]D : +18.7 • allow either to equilibrate, measure [a]D : +52.5

  5. Glycosides • Free sugar + alcohol + acid gives a glycoside • Glycosides are no longer free sugars and do not mutarotate

  6. Glycosides - disaccharides • Organic synthesis limited by protecting group chemistry needed • Bioorganic enzymatic synthesis now making oligosaccharides

  7. Disaccharides – examples

  8. Oligosaccharides – examples • Blood group antigens – extremely subtle differences in sugars in the epitope lead to important consequences in blood biochemistry

  9. Polysaccharides – examples amylose cellulose

  10. Synthetic vaccines Danishefsky et. al. Sloan-Kettering/Columbia – Synthetic vaccine against 3 types of cancer

  11. Miscellaneous reactions of free sugars

  12. Friday • Chapter 26 – Lipids and fats

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