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Characterization and Derivation of Glucose using PMP

Characterization and Derivation of Glucose using PMP. Spring 2013 Instrumental Real World Naomi Bryner David Millard. Background. Glucose, most common sugar and essential for life. Simple sugar and can lead to further knowledge of more complex sugars.

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Characterization and Derivation of Glucose using PMP

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  1. Characterization and Derivation of Glucose using PMP Spring 2013 Instrumental Real World Naomi Bryner David Millard

  2. Background • Glucose, most common sugar and essential for life. • Simple sugar and can lead to further knowledge of more complex sugars. • Critical in the production of adenosine triphosphate (ATP). • ATP is the energy source used throughout the body. • Product analyzed with nuclear magnetic resonance (NMR) and capillary electrophoresis (CE) and infrared spectroscopy (IR).

  3. Method - Derivatization • Created stock solutions of NaOH (0.3 M), PMP in MeOH (0.5 M), HCl (0.3 M) and a sodium borate buffer (0.2 M, 9.5 pH). • Dextrose (1.3512 g) added to RBF with NaOH (30 mL) and PMP (30 mL), heated in mineral oil bath with condenser at ~70°C for 30 min. • HCl (30 mL) added after cooling to neutralize reaction.

  4. Method – Extraction, Isolation & Analysis • Sample and ethyl acetate (190 mL) added to separatory funnel for extract (x 3). • Aqueous layer evaporated to dryness • Rotory evaporator for ethyl acetate, methanol • Lyophilizer for water • After sample was dried, water was added to dissolve sample, followed by another round of evaporation to dryness. • Product was analyzed with NMR, CE, and IR.

  5. Data - CE PMP peak Product peak

  6. Data - IR

  7. Data - Proton NMR Theoretical Spectrum Experimental Spectrum

  8. Data – 13C NMR Theoretical Spectrum Resultant Spectrum

  9. Results • Stock glucose can’t be examined directly; lack of chromophores. • 13C NMR: noisy baseline led to an increase of scans from 1024 to 7500 (overnight). • CE was comparison of PMP to product, NMR and IR were characterization. • Technological advancements caused difficulty in method replication(2002 -> 2013). • Week-long derivatization and tedious product isolation was worthwhile. • Ketone, permanent aspect of PMP in MeOH, was not detected in IR analysis, indicative of a product without excess PMP.

  10. References • Bruice, P. Y. In Organic Chemistry; Folchetti, N., Mullaney, R., Kaveney, D., Eds.; Pearson prentice Hall: Upper Saddle River, NJ, 2007, 5th Edition, pp 418-460. • Thibault, Pierre, and Susumu Honda. Capillary electrophoresis of carbohydrates. Totowa, NJ: Humana, 2002 • Special Thanks to: • Dr. Foy, Dr. Hu, Dr. Halligan, Amanda MacPhearson, Jesse Diehl, Delaney Caudill

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