4-O-beta-D-glucopyranosyl-D-gluconic acid (cellobionic acid) produced by ozonation of cellobiose: Isolation by HPLC and assignment of NMR chemical shifts

Mild ozonation of cellobiose in acetic acid almost exclusively favors oxidation of the reducing end, thus yielding 4-O-beta-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. C-13 and H-1 NMR chemical shifts are reported.