Well-defined glycopolymers from RAFT polymerization:: Poly(methyl 6-O-methacryloyl-α-D-glucoside) and its block copolymer with 2-hydroxyethyl methacrylate
Well-defined glycopolymers from RAFT polymerization:: Poly(methyl 6-O-methacryloyl-α-D-glucoside) and its block copolymer with 2-hydroxyethyl methacrylate
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DOI：
10.1021/ma049129
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发表时间：
2004-10-05
期刊：
影响因子：
5.5
通讯作者：
Davis, TP
中科院分区：
文献类型：
--
作者：
Albertin, L;Stenzel, M;Davis, TP
以无水乙腈为溶剂，脂肪酶催化甲基丙烯酸乙烯酯与α-D-葡萄糖苷的酯交换反应合成了糖基共聚单体甲基6-O-甲基丙烯酰基-α-D-葡萄糖苷。以良好的产率获得所需的6-O区域异构体，其结构通过H-1-H-1和H-1-C-13相关NMR光谱证实。以4-氰基戊酸-4-二硫代苯甲酸酯为链转移剂，在水溶液中直接进行无保护单体的可逆加成-断裂链转移（RAFT）聚合，得到分子量在16 ~ 103 kDa（H-1 NMR）之间、多分散性低至1.10的聚（6-O-甲基丙烯酰基-α-D-葡萄糖苷甲基酯）。其中一种聚合物与甲基丙烯酸2-羟乙酯进行扩链反应，得到新型亲水性嵌段共聚物聚[（甲基6-O-甲基丙烯酰基-α-D-葡萄糖苷）-嵌段-（甲基丙烯酸2-羟乙酯）]。
The glycomonomer methyl 6-O-methacryloyl-alpha-D-glucoside was prepared by lipase-catalyzed transesterification of vinyl methacrylate with methyl a-D-glucoside in dry acetonitrile. The desired 6-O regioisomer was obtained in good yield and its structure confirmed by H-1-H-1 and H-1-C-13 correlation NMR spectroscopy. Reversible addition-fragmentation chain transfer (RAFT) polymerization of the unprotected monomer was performed directly in aqueous solution using (4-cyanopentanoic acid)-4-dithiobenzoate as the chain transfer agent to give poly(methyl 6-O-methacryloyl-alpha-D-glucoside) with M-n between 16 and 103 kDa (H-1 NMR) and polydispersities as low as 1.10. Chain extension of one of these polymers with 2-hydroxyethyl methacrylate afforded the novel hydrophilic-hydrophilic block copolymer poly[(methyl 6-O-methacryloyl-alpha-D-glucoside)-block-(2-hydroxyethyl methacrylate)].