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-gl ucose (1b) and 2,6-diamino-2,6-dideoxy-D-glucose (5b) to give new aminopoly saccharides 2 and 6, respectively. The polymerization of Ib took place in t he presence of acetic acid via Amadori rearrangement to give 2 having an am inoketose structure. On the other hand, the spontaneous polymerization of 5 b proceeded through the selective condensation of a hydroxy group at positi on 1 with an amino group at position 6 to produce 6 with a glycosylamine st ructure. The molecular weights were determined by gel permeation chromatogr aphic analyses after acetylation of the product polysaccharides. (C) 1999 E lsevier Science Ltd. All rights reserved.