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Precision Molecular Architecture of Sugar Balls

糖球的精密分子结构

基本信息

批准号：
10450351
负责人：
AOI Keigo
金额：
$ 3.71万
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：
1998
资助国家：
日本
起止时间：
1998 至 1999
项目状态：
已结题

项目摘要

Sugar-substituted α-amino acid N-carboxyanhydrides (glycoNCAs), i.e., O-(tetra-O-acetyl-β-D-glucopyranosyl)-L-serine NCA (2a) and O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine NCA (2b), were successfully used for introduction of a monoglycopeptide unit to each terminal primary amino group of a dendrimer. Well-defined dendrimer-based artificial glycoconjugates, O-(β-D-glucopyranosyl)-L-serine-persubstituted poly(amido amine) (PAMAM) dendrimer (3a) and O-(2-acetamido-2-depxy-β-D-glucopyranosyl)-L-serine-persubstituted PAMAM dendrimer (3b), were synthesized by polymer reaction of PAMAM dendrimer with 2a and 2b respectively, followed by deacetylation with hydrazine monohydrate.Sugar-containing amphiphilic surface-block poly (amido amine) (PAMAM) dendrimer was synthesized as follows. Benzyloxycarbonyl (z)-protected ethylenediamine was used as a partial-protected initiator core. The 1st divergent step was carried out by repeating Michael addition and amide formation reaction to afford half-generational methyl ester-ended hemispherical block. A hydrophobic hemispherical block was obtained by the reaction of an excess amount of n-hexylamine with the half-generated dendritic block. After removal of the core-Z group, the 2nd divergent PAMAM construction was conducted in a similar manner to the 1st process. Introduction of sugar residues was successfully achieved by using the glycoNCA 2b. After deacetylation of the sugar moiety, a sugar-containing surface-block dendrimer was isolated.Molecular recognition ability of the sugar balls and the half-sugar ball was investigated by a hemagglutination inhibition test using wheat germ agglutinin (WGA) lectin. Effective molecular recognition ability of the arranged sugar residues on the surface of dendrimers was qualitatively demonstrated.

糖取代α-氨基酸n -羧基氢化（glycoNCAs），即O-（四-O-乙酰基-β- d -葡萄糖吡喃基）- l-丝氨酸NCA （2a）和O-（2-乙酰基-3,4,6-三-O-乙酰基-2-脱氧-β- d -葡萄糖吡喃基）- l-丝氨酸NCA (2b)，成功地将单肽单元引入到树状大分子的每个末端初级氨基上。通过PAMAM树状大分子与2a和2b的聚合反应，分别合成了O-(β-D-glucopyranosyl)- l-丝氨酸过取代聚氨基胺（PAMAM）树状大分子（3a）和O-(2-乙酰氨基-2-depxy-β-D-glucopyranosyl)- l-丝氨酸过取代PAMAM树状大分子（3b），并与一水合肼脱乙酰化。含糖两亲性表面嵌段聚胺胺（PAMAM）树状大分子的合成方法如下。采用苯氧羰基(z)保护型乙二胺作为部分保护型引发剂芯。第一步是通过重复Michael加成反应和酰胺生成反应，得到半代甲基酯端半圆嵌段。通过过量的正己胺与半生成的树突块反应得到疏水半球形块。去除核心- z基团后，以类似于第一次过程的方式进行第二次发散PAMAM构建。利用glycoNCA 2b成功地实现了糖残基的引入。在糖部分去乙酰化后，分离出含糖表面阻滞的树状大分子。采用小麦胚芽凝集素（WGA）凝集素抑制血凝试验，研究了糖球和半糖球的分子识别能力。定性地证明了树状大分子表面排列的糖残基的有效分子识别能力。