4- <i>O</i> -β- <scp>d</scp> -GLUCOPYRANOSYL- <scp>d</scp> -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: Sodra Cell R&D, NO-3482 Tofte, Norway. ††Current address: The Norwegian Pulp and Paper Research Institute (PFI), Hogskoleringen 6B, NO-7491 Trondheim, Norway.