Studies on Amino-hexoses. XVII. Identification of the Deamination Products from d -Glucosaminitol

The nitrous deamination products of d-glucosaminitol were fractionated with a Dowex-1 free base column after the reaction mixture had been reduced with sodium borohydride. The chromatography gave discrete five peaks, four of which were identified as 2-deoxy-d-arabino-hexitol, 2-deoxy-d-ribo-hexitol, 2-hydroxymethyl-2-deoxy-d-arabino(or ribo)-pentitol and d-mannitol in a total yield over 90%. The nitrous deamination products fractionated with a Dowex-1 borate column were identified as 2-deoxy-d-arabino-hexose, 2-deoxy-d-erythro-3-hexulose, 2-hydroxymethyl-2-deoxy-d-arabino(or ribo)-pentose and d-mannitol. The formation of products other than d-mannitol was interpreted in terms of intramolecular rearrangement accompanying nitrous deamination.