1. Organic Chemistry of Sugar Presented by: Amber Lloyd

2. Purpose Aspartame Sucralose Saccharin Sucrose

3. Why is this important?  Natural vs. artificial controversy

4. What is sugar?  Typically refers to all carbohydrates  General formula:  C n (H 2 O) n  Are all sweeteners carbohydrates?  Typically refers to all carbohydrates  General formula:  C n (H 2 O) n  Are all sweeteners carbohydrates? Image source: http://333oee3bik6e1t8q4y139009mcg.wpengine.netdna-cdn.com/wp-content/uploads/2014/03/sweeteners_sugar.jpg

5. The Original Sweetener -- Sucrose  Composed of 2 monosaccharides  Structural differences between:  Raw vs. refined?  From sugar cane vs. sugar beet?  Primary reference for other sweeteners http://www.wpclipart.com/science/atoms_molecules/molecules/sucrose.png.html

6. Synthesis of Sucrose  Formation – Dehydration Reaction

7. Artificial Sweeteners Focus on: Sucralose, Saccharin & Aspartame

8. Sucralose  “Cousin” of sucrose  Structurally the most closely related artificial sweetener  Sweetest sugar derivative  “Cousin” of sucrose  Structurally the most closely related artificial sweetener  Sweetest sugar derivative http://www.zoetstoffen.nl/sites/zoetstoffen.nl/files/zoetstof/sucralose2.png

9. Synthesis of Sucralose  Starting material?  Why so many steps to replace 3 –OH with –Cl? http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392

10. Saccharin  Health benefits instead of dangers?!  Presidential support

11. Synthesis of Saccharin Original Method Maumee Method Images: http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392

12. The Current Face of Controversy -- Aspartame Image: http://collectivelyconscious.net/wp-content/uploads/2014/05/new-study-fda-approved-levels-of-aspartame-distort-brain-function-kill-brain-cells2.jpg

13. Aspartame (continued)  Composed of 2 amino acids  Real fuel behind the controversy: side products produced during degradation  Composed of 2 amino acids  Real fuel behind the controversy: side products produced during degradation

14. Synthesis of Aspartame  Two methods of production  Coupling vs. Enzymatic

15. Conclusion Structurally similar to Sucrose? Able to be metabolize? If yes– into what? Sucrose Glucose & Fructose SucraloseYes SaccharinNo AspartameNo Aspartic acid, phenylalanine, and methanol

16. Written Assignment  I am proposing to create a children’s book that looks at the sweeteners discussed during this presentation in a colorful way. The goal of this children’s book would be to capture the interest of young scientist in such a way that they can really see and understand how natural and artificial sweeteners are truly different on a chemical level.

17. References  McGuire, Michelle. Beerman, Kathy A, Nutritional Sciences: From Fundamentals to Food; Wadsworth, Cengage Learning: 2007.  Ouellette, Robert J., Rawn, J. David. Organic Chemistry: Prentice Hall; 1997, pg 759-762  Belitz, H.D,, Grosch, Werner, Schieberle, Peter. Food Chemistry, 3 Ed; Springer Science and Business Media: 2009, pg 868-875  McMurry, John. Fundamentals of Organic Chemistry: Cengage Learning; 2010, pg 490  Solomons, TW Graham; Fryhle, Craig B. Organic Chemistry 11 Ed : Wiley: 2013  Cheminfo2011: http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392 (accessed: November 1, 2014)http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392  Saccharin information center: saccharin.org (accessed: November 1, 2014)  Aspartame information center: aspartame.org (accessed: November 1, 2014)  McGuire, Michelle. Beerman, Kathy A, Nutritional Sciences: From Fundamentals to Food; Wadsworth, Cengage Learning: 2007.  Ouellette, Robert J., Rawn, J. David. Organic Chemistry: Prentice Hall; 1997, pg 759-762  Belitz, H.D,, Grosch, Werner, Schieberle, Peter. Food Chemistry, 3 Ed; Springer Science and Business Media: 2009, pg 868-875  McMurry, John. Fundamentals of Organic Chemistry: Cengage Learning; 2010, pg 490  Solomons, TW Graham; Fryhle, Craig B. Organic Chemistry 11 Ed : Wiley: 2013  Cheminfo2011: http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392 (accessed: November 1, 2014)http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392  Saccharin information center: saccharin.org (accessed: November 1, 2014)  Aspartame information center: aspartame.org (accessed: November 1, 2014)