A new type of artificial glycoconjugate polymer: A convenient synthesis and its interaction with lectins
A new type of artificial glycoconjugate polymer: A convenient synthesis and its interaction with lectins
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DOI：
10.1021/ma961681e
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发表时间：
1997-04-07
期刊：
影响因子：
5.5
通讯作者：
Akaike, T
中科院分区：
文献类型：
--
作者：
Kobayashi, K;Tsuchida, A;Akaike, T
设计了一条合成新型人工糖共轭聚合物的简便路线，以低聚糖作为识别信号来开发生物医学材料。用碳酸氢铵在乳糖和N，N‘-二乙酰基壳二糖的还原端引入氨基，再与对乙烯基苯甲酰氯反应。N-糖苷在一个烧瓶中立体地进行，只得到β-糖苷，没有任何保护和去保护步骤；得到的对乙烯基苯甲酰胺糖苷衍生物在60℃下以2，2‘-偶氮二异丁腈为引发剂与丙烯酰胺在二甲基亚砜中进行均聚合和共聚，并通过琼脂双向免疫扩散试验和血凝活性抑制试验研究了共聚物与凝集素的相互作用。凝集素与这些糖共聚物的特异性与报道的天然糖偶联物相似。小麦胚芽凝集素凝集素与poly((p-vinylbenzamido)-beta-diacetylchitobiose)的结合比低聚糖本身高10(3)倍。这种增强归因于疏水性苯苷元的存在以及沿着聚合物链的高密度、多天线的二糖配体的存在。本发明的合成方法可用于将具有生物重要性的复杂低聚糖引入糖共聚物。
A convenient synthetic route to a new type of artificial glycoconjugate polymer has been designed to develop biomedical materials using oligosaccharide moieties as recognition signals. An amino function was introduced to the reducing end of lactose and N,N'-diacetylchitobiose with ammonium hydrogen carbonate and then was allowed to react with p-vinylbenzoyl chloride. The N-glycosidation proceeded stereospecifically in one flask to give only the beta-glycoside without any protection and deprotection steps; The resulting p-vinylbenzamide glycoside derivatives were homo- and copolymerized with acrylamide using 2,2'-azobisisobutyronitrile as initiator in dimethyl sulfoxide at 60 degrees C. The interaction of the glycopolymers with lectins was investigated by means of a two-dimensional immunodiffusion test in agar and inhibition of the hemagglutinating activity. The specificity of lectins with these glycopolymers was similar to that reported for naturally-occurring glycoconjugates. Binding between wheat germ agglutinin lectin (WGA) and poly((p-vinylbenzamido)-beta-diacetylchitobiose) was increased by 10(3) times compared with that of the oligosaccharide itself. The enhancement was attributed to the presence of the hydrophobic phenyl aglycon as well as the high density, multiantennary disaccharide ligands along the polymer chain. The present synthetic method is useful to introduce biologically important, complex oligosaccharides into glycopolymers.