Synthesis of new aminopolysaccharides by polymerization of 6-amino-6-deoxy-D-glucose and 2,6-diamino-2,6-dideoxy-D-glucose

This paper describes the spontaneous polymerization of 6-amino-6-deoxy-D-glucose (1b) and 2,6-diamino-2,6-dideoxy-D-glucose (5b) to give new aminopolysaccharides 2 and 6, respectively. The polymerization of 1b took place in the presence of acetic acid via Amadori rearrangement to give 2 having an aminoketose structure. On the other hand, the spontaneous polymerization of 5b proceeded through the selective condensation of a hydroxy group at position 1 with an amino group at position 6 to produce 6 with a glycosylamine structure. The molecular weights were determined by gel permeation chromatographic analyses after acetylation of the product polysaccharides.