Chemoenzymatic synthesis of narrow-polydispersity glycopolymers:: Poly(6-O-vinyladipoly-D-glucopyranose)
Chemoenzymatic synthesis of narrow-polydispersity glycopolymers:: Poly(6-O-vinyladipoly-D-glucopyranose)
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DOI：
10.1021/bm034199u
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发表时间：
2004-03-01
影响因子：
6.2
通讯作者：
Davis, TP
中科院分区：
文献类型：
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作者：
Albertin, L;Kohlert, C;Davis, TP
以己二酸二乙烯酯和α-D-吡喃葡萄糖为原料，在无水乙腈和丙酮中，通过脂肪酶催化酯交换反应制备了糖基共聚单体6-O-乙烯基己二酸-D-吡喃葡萄糖。以良好的产率获得所需的6-O区域异构体，并通过相关NMR光谱确认其结构。以黄原酸酯和二硫代氨基甲酸酯为链转移剂，在质子介质中进行无保护单体的可控自由基聚合，得到分子量分别为17和19 kDa（SEC）的聚（6-O-乙烯基己二酰-D-吡喃葡萄糖），其多分散性低至1.10。据我们所知，这是第一个窄多分散性的聚（乙烯基酯）样糖共聚物的例子。
The glycomonomer 6-O-vinyladipoyl-D-glucopyranose was prepared via lipase catalyzed transesterification of divinyladipate with alpha-D-glucopyranose in dry acetonitrile and acetone. The desired 6-O regioisomer was obtained in good yield, and its structure was confirmed by correlation NMR spectroscopy. Controlled radical polymerization of the unprotected monomer was performed in protic media using both xanthate and dithiocarbamate as chain transfer agents to give poly(6-O-vinyladipoyl-D-glucopyranose) with M-n of 17 and 19 kDa (SEC) respectively and a polydispersity as low as 1.10. To the best of our knowledge, this is the first example of a narrow-polydispersity, poly(vinyl ester)-like glycopolymer.