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Synthesis of Perbenzoylated Carbohydrates in Preparation for Anthocyanin Pigment Characterization

Synthesis of Perbenzoylated Carbohydrates in Preparation for Anthocyanin Pigment Characterization. Brandon Lew March 15, 2006. Introduction. Purpose: To develop a technique for carbohydrate characterization through NMR so that anthocyanin carbohydrate tails may be characterized. Anthocyanins.

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Synthesis of Perbenzoylated Carbohydrates in Preparation for Anthocyanin Pigment Characterization

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  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.jpg http://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 Chain Chair

  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) Excited State Magnetic Field EM radiation Radio wave Detector 1H/13C Ground State

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

  12. Protocol 1 Results: HPLC of perbenzoylated maltose

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

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

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

  16. Protocol 2 Results: HPLC of perbenzoylated β glucose

  17. Procedure 2 Results: 1H 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

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