Glycoconjugated polymer. I. Synthesis and characterization of amphiphilic polystyrenes with glucose, maltose, and maltohexaose as hydrophilic segments

Glucosyl styrene (1a), maltosyl styrene (1b), and maltohexaosyl styrene (1c) were prepared by the glycosylation of 4-vinylbenzyl alcohol with the corresponding glycosyl trichloroacetimidates with boron trifluoride diethyl ether complex. The copolymerizations of 1a-1c with styrene were carried out with 2,2'-azobis(2-methylpropionitrile) as an initiator in dry NN-dimethylformamide at 60 degreesC, and this was followed by deacetylation to produce amphiphilic polystyrenes with glucose (3a), maltose (3b), and maltohexaose (3c) as hydrophilic segments. 3 showed various solubility characteristics that were dependent on the content of glucose residues, especially within a range of 20-50 wt%. The solubility characteristics of 3, related to the copolymer composition, indicated that the hydrophilic property was remarkably improved with an increased number of glucose units, that is, in the order 3a < 3b much less than 3c. The results described in this article provide useful information for the design of glycoconjugated architectures with desired amphiphilic properties. (C) 2001 John Wiley & Sons, Inc.