Chemical modification of chitosan. 10. Synthesis of dendronized chitosan-sialic acid hybrid using convergent crafting of preassembled dendrons built on gallic acid and tri(ethylene glycol) backbone

被引:64
作者
Sashiwa, H
Shigemasa, Y
Roy, R [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
[2] Tottori Univ, Fac Engn, Tottori 6808552, Japan
关键词
D O I
10.1021/ma001832k
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Sialic acid dendrons bearing a focal aldehyde end group were synthesized by a reiterative amide bond strategy. Polyamine-ending trivalent (G = 1) and nonavalent (G = 2) dendrons having gallic acid as branching unit and tri(ethylene glycol) as spacer-arm were prepared and initially attached to a sialic acid p-phenylisothiocyanate derivative. The focal aldehyde sialodendrons were then convergently grafted onto the polysaccharide chitosan backbone by reductive amination in 76-80% yields. The degrees of substitution (DS) of the sialodendrimer in the hybrids were 0.13 (G = 1) and 0.06 (G 2), which indicates that 87% and 40% of the sialodendrons were attached to the primary amino groups of chitosan. The water solubility of these novel hybrids was further improved by N-succinylation of the remaining amine functionality.
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收藏
页码:3905 / 3909
页数:5
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