1. Synthesis of Perbenzoylated Carbohydrates in Preparation for Anthocyanin Pigment Characterization Brandon Lew March 15, 2006

2. Introduction Purpose: To develop a technique for carbohydrate characterization through NMR so that anthocyanin carbohydrate tails may be characterized.

3. Anthocyanins http://www.mariquita.com/images/photogallery/strawberries.jpghttp://www.personal.psu.edu/staff/m/h/mhl100/images/blueberries.jpg

4. Carbohydrate Tails Anthocyanidin Base

5. Anthocyanin Characterization NMR of anthocyanins Seeram et al. 2002 Separation of tails Takeoka et al. 2005 Combine to perform NMR on separated tails

6. Carbohydrates ChairChain

7. Perbenzoylation Levene and Meyer (1927) Glucose D’Accorso et al. (1981) NMR data of many monosaccharides

8. Perbenzoylation (Protocol 1) β-glucose Perbenzoylated-β-glucose

9. Purification Thin-layer chromatography (TLC) Column chromatography High-pressure liquid chromatography (HPLC) http://www.hamline.edu/depts/chemistry/facility/images/hplc.jpg

10. Nuclear Magnetic Resonance Spectroscopy (NMR) 1 H/ 13 C EM radiation Excited State Ground State Radio wave Detector Magnetic Field

11. Protocol 1 Results: 1 H NMR of perbenzoylated β glucose

12. Protocol 1 Results: HPLC of perbenzoylated maltose

13. Protocol 1 Results: 13 C NMR of perbenzoylated maltose

14. Perbenzoylation (Protocol 2) β-glucose Perbenzoylated-β-glucose

15. Protocol 2 Results: 1 H NMR of perbenzoylated β glucose

16. Protocol 2 Results: HPLC of perbenzoylated β glucose

17. Procedure 2 Results: 1 H NMR of perbenzoylated α glucose

18. Conclusion Protocol 1 – contaminated Some disaccharides selectively benzoylated β-glucose Perbenzoylated-β-glucose

19. Conclusion Protocol 2 – purer, quicker Perbenzoylation works for characterization β-glucose Perbenzoylated-β-glucose

20. Future Work Use perbenzoylation to characterize carbohydrate tails of anthocyanins Anthocyanins differ by their tails Important for developing anti-oxidant food additives

21. Acknowledgements Dr. Matachek Hamline University Ms. Fruen Ms. Richter, Bill Mitchell Team Research

22. Synthesis of Perbenzoylated Carbohydrates in Preparation for Anthocyanin Pigment Characterization Brandon Lew March 15, 2006