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
Carbohydrate Tails Anthocyanidin Base
Anthocyanin Characterization NMR of anthocyanins Seeram et al Separation of tails Takeoka et al Combine to perform NMR on separated tails
Carbohydrates ChairChain
Perbenzoylation Levene and Meyer (1927) Glucose D’Accorso et al. (1981) NMR data of many monosaccharides
Perbenzoylation (Protocol 1) β-glucose Perbenzoylated-β-glucose
Purification Thin-layer chromatography (TLC) Column chromatography High-pressure liquid chromatography (HPLC)
Nuclear Magnetic Resonance Spectroscopy (NMR) 1 H/ 13 C EM radiation Excited State Ground State Radio wave Detector Magnetic Field
Protocol 1 Results: 1 H NMR of perbenzoylated β glucose
Protocol 1 Results: HPLC of perbenzoylated maltose
Protocol 1 Results: 13 C NMR of perbenzoylated maltose
Perbenzoylation (Protocol 2) β-glucose Perbenzoylated-β-glucose
Protocol 2 Results: 1 H NMR of perbenzoylated β glucose
Protocol 2 Results: HPLC of perbenzoylated β glucose
Procedure 2 Results: 1 H NMR of perbenzoylated α glucose
Conclusion Protocol 1 – contaminated Some disaccharides selectively benzoylated β-glucose Perbenzoylated-β-glucose
Conclusion Protocol 2 – purer, quicker Perbenzoylation works for characterization β-glucose Perbenzoylated-β-glucose
Future Work Use perbenzoylation to characterize carbohydrate tails of anthocyanins Anthocyanins differ by their tails Important for developing anti-oxidant food additives
Acknowledgements Dr. Matachek Hamline University Ms. Fruen Ms. Richter, Bill Mitchell Team Research
Synthesis of Perbenzoylated Carbohydrates in Preparation for Anthocyanin Pigment Characterization Brandon Lew March 15, 2006