Journal of Polymer Science Part A: Polymer Chemistry, Vol.55, No.3, 395-403, 2017
Synthesis of Amphiphilic Block Copolymer Consisting of Glycopolymer and Poly(L-lactide) and Preparation of Sugar-coated Polymer Aggregates
The block glycopolymer, poly(2-(alpha-D-mannopyranosyloxy) ethyl methacrylate)-b-poly(L-lactide) (PManEMA-b-PLLA), was synthesized via a coupling approach. PLLA having an ethynyl group was successfully synthesized via ring-opening polymerization using 2-propyn-1-ol as an initiator. The ethynyl functionality of the resulting polymer was confirmed by MALDI-TOF mass spectroscopy. In contrast, PManEMA having an azide group was prepared via AGET ATRP using 2-azidopropyl 2-bromo-2-methylpropanoate as an initiator. The azide functionality of the resulting polymer was confirmed by IR spectroscopy. The Cu(I)-catalyzed 1,3-dipolar cycloaddition between PLLA and PManEMA was performed to afford PManEMA-b-PLLA. The block structure was confirmed by H-1 NMR spectroscopy and size exclusion chromatography. The aggregating properties of the block glycopolymer, PManEMA(16k)-b-PLLA(6.4k) = (M-n,M-PManEMA = 16,000, M-n,M-PLLA = 6400) was examined by H-1 NMR spectroscopy, fluorometry using pyrene, and dynamic light scattering. The block glycopolymer formed complicated aggregates at concentrations above 21 mg.L-1 in water. The D-mannose presenting property of the aggregates was also characterized by turbidimetric assay using concanavalin A. (C) 2016 Wiley Periodicals, Inc.