4-O-β-d-GLUCOPYRANOSYL-d-GLUCONIC ACID (CELLOBIONIC ACID) PRODUCED BY OZONATION OF CELLOBIOSE: ISOLATION BY HPLC AND ASSIGNMENT OF NMR CHEMICAL SHIFTS

Abstract

Mild ozonation of cellobiose in acetic acid almost exclusively favors oxidation of the reducing end, thus yielding 4-O-β-d-glucopyranosyl-d-gluconic acid (“cellobionic acid”). This compound can be quantitatively separated from the substrate by preparative HPLC using acetonitrile/phosphate buffer on an aminopropyl silica column. The product was identified using one and two dimensional NMR techniques. ¹³C and ¹H NMR chemical shifts are reported.

†Current address: Södra Cell R&D, NO-3482 Tofte, Norway.

††Current address: The Norwegian Pulp and Paper Research Institute (PFI), Høgskoleringen 6B, NO-7491 Trondheim, Norway.

Keywords:

• Cellulose
• Cellobiose
• Glucose
• Ozonation
• Ozone
• Bleaching
• Pulp
• Oxidation
• Reducing end
• Cellobionic acid
• Aldonic acid
• NMR spectroscopy
• 2D-NMR
• Chemical shift
• HPLC
• High pressure liquid chromatography

ACKNOWLEDGMENTS

Thanks to MSc. Odd Inge Optun at SINTEF UNIMED and to Professor Hans Grasdalen at NTNU Department of Biotechnology for helpful discussions of the NMR spectra. This work has received financial support from the Norwegian Research Council (NFR) and from the Norwegian Pulp and Paper Association (TFB).

Notes

†Current address: Södra Cell R&D, NO-3482 Tofte, Norway.

††Current address: The Norwegian Pulp and Paper Research Institute (PFI), Høgskoleringen 6B, NO-7491 Trondheim, Norway.