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Precision Synthesis of Glycopeptide-Type Sugar Balls and Development of Their Molecular Catalyst and Molecular Recognition

糖肽型糖球的精密合成及其分子催化剂和分子识别的开发

基本信息

批准号：
09450349
负责人：
OKADA Masahiko
金额：
$ 6.66万
依托单位：
NAGOYA UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (B)
财政年份：
1997
资助国家：
日本
起止时间：
1997 至 1999
项目状态：
已结题

项目摘要

1. Precision Synthesis of Glycopeptide-Type Sugar Balls :An efficient synthetic method via a reaction of primary amine-terminated dendrimer with sugar derivative-substituted α-amino acid N-carboxyanhydride (NCA) was established for glycopeptide-type sugar balls of well-defined structure. A variety of glycopeptide type-sugar balls were synthesized by the reactions of poly(amido amine) dendrimers of up to the eighth generation with glucose, galactose, and N-acetylglucosamine derivative-substituted L-serine NCAs.2. Analysis of Propagation Rate Acceleration in Radial-Growth Polymerization (RGP) :Ring-opening polymerization of NCAs with primary anime-terminated dendrimer as an initiator was kinetically investigated by means of conductivity measurement. On the basis of the effects of solvents, substituents, temperature, and added cyano-terminated dendrimer on the propagation rate constant, it was concluded that the observed acceleration was due to the increased monomer concentration near the dendrimer surface and the enhanced collision probability arising from the radial-growth from the surface as well.3. Evaluation of Glycopeptide-Type Sugar Balls as Biofunctional Materials :Encapsulation of low molecular weight compounds inside glycopeptide-type sugar balls was investigated using sodium 8-anilino-1-naphthalenesulfonate (ANS) as a probe. The number of the encapsulated ANS molecules appreciably increased when poly(amido amine) dendrimer of the eighth generation was allowed to react with N-acetylglucosamine derivative-substituted NCA in dimethyl sulfoxide. Inhibition experiments of lectin-induced hemagglutination proved that the glycopeptide-type sugar balls possessed much higher molecular recognition ability than the corresponding mono- or oligosaccharides.

1.糖肽型糖球的精密合成：通过伯胺末端树枝状大分子与糖衍生物取代的α-氨基酸N-羧酸酐（NCA）反应，建立了结构明确的糖肽型糖球的高效合成方法。以第八代聚酰胺胺树枝状大分子与葡萄糖、半乳糖、N-乙酰氨基葡萄糖衍生物取代的L-丝氨酸NCAs反应合成了多种糖肽型糖球。2．径向生长聚合(RGP) 中的传播速率加速分析：通过电导率测量对以初级氨基封端的树枝状聚合物作为引发剂的NCAs 的开环聚合进行动力学研究。根据溶剂、取代基、温度和添加的氰基树枝状聚合物对增长速率常数的影响，得出结论：观察到的加速是由于树枝状聚合物表面附近单体浓度的增加以及表面径向生长导致的碰撞概率增加所致。 3．糖肽型糖球作为生物功能材料的评价：使用 8-苯胺基-1-萘磺酸钠 (ANS) 作为探针，研究了糖肽型糖球内低分子量化合物的封装。当第八代聚(酰胺基胺)树枝状聚合物与N-乙酰葡糖胺衍生物取代的NCA在二甲亚砜中反应时，封装的ANS分子的数量明显增加。凝集素诱导的血凝抑制实验证明，糖肽型糖球比相应的单糖或寡糖具有更高的分子识别能力。