Chemoenzymatic synthesis of narrow-polydispersity glycopolymers:: Poly(6-O-vinyladipoly-D-glucopyranose)

被引:91
作者
Albertin, L
Kohlert, C
Stenzel, M
Foster, LJR
Davis, TP [1 ]
机构
[1] Univ New S Wales, Sch Chem Engn & Ind Chem, Ctr Adv Macromol Design, Sydney, NSW 2052, Australia
[2] Univ New S Wales, Sch Biotechnol & Biomol Sci, Sydney, NSW 2052, Australia
关键词
D O I
10.1021/bm034199u
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
引用
收藏
页码:255 / 260
页数:6
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