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

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Presentation transcript:

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