
%0 Journal Article
%A Ingles, DL 
%T Chemistry of Non-Enzymic Browning. VI. The reaction of Aldoses with Amine Bisulphites
%J Australian Journal of Chemistry
%D 1959/06/01
%V 12
%N 2
%P 275-279
%K 
%R https://doi.org/10.1071/CH9590275
%U https://www.publish.csiro.au/paper/CH9590275 
%X 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. 
