1 / 22

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.

jana
Télécharger la présentation

Synthesis of Perbenzoylated Carbohydrates in Preparation for Anthocyanin Pigment Characterization

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  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

More Related