Chemistry of Non-Enzymic Browning. VI. The reaction of Aldoses with Amine Bisulphites

Abstract

The crystalline glucose-aniline bisulphite addition compound, D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl anilinium sulphonate, was prepared from the reaction of D-glucose with aniline bisulphite in water and in methanol. The D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl piperidinium sulphonate was prepared by adding piperidine bisulphite to preformed N-phenyl-D-glucosylamine. Other new compounds of similar structure were prepared from the reaction of aniline bisulphite with D -galactose and D-mannose. cycloHexylamine bisulphite reacted with D-glucose to form crystalline D-glycero-D-ido-1,2,3,4,5,6-hexahydroxyhexyl cyclohexylammonium sulphonate. When treated with aniline this compound formed D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl cyclohexylammonium sulphonate. The D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl potassium and anilinium sulphonates were interconverted by use of a cation-exchange resin. Acetylation of the anilinium sulphonate in pyridine gave the tetra-acetate of N-phenyl-D-glucosylamine.