Electrosynthesis of oligosaccharide glycamines

1-Amino-1-deoxy-4-O-β-d-glucopyranosyl-d-glucitol and 1-amino-1-deoxy-4-O-β-d-galactopyranosyl-d-glucitol were obtained in high purity and almost quantitative yield by electro-reduction of the respective oximes of cellobiose and lactose. The methodology was extended to mixture of hepta-, octa- and nona-saccharides obtained by enzymatic degradation of xyloglucan. The oximes were prepared in situ from the above-mentioned oligosaccharides and a mixture of hydroxylammonium sulfate and ammonium acetate at pH 4–6 in aqueous solutions. Electrosynthesis of the glycamines was carried out at either constant current or constant potential in a divided electrolysis cell with a working mercury cathode and a platinum-coated titanium anode separated by a cation-selective membrane.