108B Carbohydrate Activity

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CHEM 108B UCSC, Binder CARBOHYDRATE ACTIVITY Structural Conventions – complete #1-6 before the first carbohydrates lecture to facilitate understanding in lecture (due in discussion 2/29-3/4). The last two problems and definitions are due in discussion the following week (3/7-3/11). Use chapter 25 of the McMurry text to learn this as you go but some terms may require a quick google search. Define the terms on the next page as you go along. 1. Draw one example of each of the following types of monosaccharides (there may be several correct answers) and indicate the number of possible stereoisomers while keeping the same D/L configuration. a. D-Aldotriose b. L-Ketotetrose c. L-Aldopentose d. D-Ketohexose e. L-Aldohexose 2. Draw Fischer projections of the following: a. The C2 epimer of D-Glucose b. The C3 epimer of D-Glucose c. The C4 epimer of D-Glucose 3. Each monosaccharide from #1-2 can act as a nucleophile or electrophile. Redraw sugars #1d and #1e and indicate the functional groups that could act as nucleophiles and those that can serve as electrophiles. 4. Draw a skeleton Haworth projection and chair conformation of a D- monosaccharide in closed form: a 6-membered oxygen-containing ring without the hydroxyl groups. 5. Draw Haworth projections for the following (consult Fig 25.3 of McMurry; memorize the structure of D-Glucose for the final exam). What is the relationship between a & b; between a & c? a. α-D-Allopyranose b. β-D-Allopyranose c. α-D-Glucopyranose d. β-D-Glucopyranose e. α-D-Idopyranose f. β-D-Idopyranose 6. Draw the chair conformations for the monosaccharides in problem 5. 7. Draw the Haworth projection and chair conformation for the β-anomer of the disaccharide formed between D-Idopyranose and D-Allopyranose by a α-1,6- glycosidic bond (consult Fig 25.3 of McMurry). 8. Draw the Haworth projection and chair conformation for the α-anomer of the disaccharide formed between D-Idopyranose and D-Allopyranose by a β-1,6- glycosidic bond (consult Fig 25.3 of McMurry). 1 CHEM 108B UCSC, Binder Vocabulary – Be familiar with these terms for the exam. 1. Carbohydrate 10. Tetrose 19. Anomers 2. Monosaccharide 11. Pentose 20. Epimers 3. Disaccharide 12. Hexose 21. Furanose 4. Trisaccharide 13. Fischer Projection 22. Pyranose 5. Oligosaccharide 14. Pentultimate Carbon 23. Glycoside 6. Polysaccharide 15. D-Monosaccharide 24. Glycosidic Bond 7. Aldose 16. L-Monosaccharide 8. Ketose 17. Hemiacetal 9. Triose 18. Anomeric Carbon Carbohydrates are an essential component in our diets, but the form and quantity of sugars we take in on a daily basis (largely due to marketing campaigns and the “deliciousness” of convenience foods) is having an adverse effect on the health of Americans. Take some time at home to research DIABETES, a disease that is affecting more and more of our population at an alarmingly increasing rate. What is the difference between Type I and Type II diabetes and what can we do to decrease our risk factors? 2 .

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