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Synthesis of Biodegradable Polymer Having Saccharide Chai

含糖链的可生物降解聚合物的合成

基本信息

批准号：
13558071
负责人：
HATANAKA Kenichi
金额：
$ 6.08万
依托单位：
The University of Tokyo
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (B)
财政年份：
2001
资助国家：
日本
起止时间：
2001 至 2003
项目状态：
已结题

项目摘要

On D-lactose, C-6 and C-6' which have the primary hydroxy groups were selectively triphenylmethylated and the remaining secondary hydroxy groups were acetylated. During detriphenylmethylation, acyl migration occurred to give acetylated lactose having free hydroxy groups on C-6 and C-4'. Polycondensation of the obtained 1,2,3,2',3',6'-hexa-ο-acetyl-D-lactose and terephthaloyl chloride gave the aromatic polyester having lactose in the main chain.Maltose was regioselectively substituted and the obtained derivative was polymerized in order to obtain a biodegradable polymer. Two primary hydroxyl groups of maltose were tosylated and the remaining secondary hydroxyl groups were acetylated. The tosyl group was replaced with azido group. The azidomaltose derivative was reacted with telephthaloyl chloride to give amide compound.Partial carboxymethylation of b-cyclodextrin was investigated. The carboxymethylation of b-cyclodextrin with chloroacetic acid and sodium hydroxide in water sokution was difficult to give the product. On the other hand, di-ο-carboxymethylated b-cyclodextrin was obtained by using potassium hydroxide as base. When bromoacetic acid was used instead of chloroacetic acid, di-ο-carboxymethylated b-cyclodextrin was obtained in shorter time. The reaction of b-cyclodextrin with methyl chloroacetate and sodium hydride in dimethylformamide solusion also gave di-ο-carboxymethylated b-cyclodextrin with the hydrolysis of methyl ester. Condensation reaction of di-ο-carboxymethylated b-cyclodextrin with hexamethylendiamine gave polyamide of which the molecular weight was 10^4.

在D-乳糖上，具有伯羟基的C-6和C-6'被选择性地三苯甲基化，并且剩余的仲羟基被乙酰化。在β-苯基甲基化过程中，发生酰基迁移，得到在C-6和C-4 '上具有游离羟基的乙酰化乳糖。将得到的1，2，3，2 ′，3 ′，6 ′-六-O-乙酰基-D-乳糖与对苯二甲酰氯进行缩聚，得到主链含有乳糖的芳香族聚酯，对麦芽糖进行区域选择性取代，使得到的衍生物聚合，得到生物降解性聚合物。麦芽糖的两个伯羟基被甲苯磺酰化，其余的仲羟基被乙酰化。甲苯磺酰基被叠氮基取代。将叠氮麦芽糖衍生物与对苯二甲酰氯反应生成酰胺化合物，研究了b-环糊精的部分羧甲基化反应。β-环糊精在水溶液中用氯乙酸和氢氧化钠进行羧甲基化反应，很难得到产物。另一方面，通过使用氢氧化钾作为碱获得二-o-羧甲基化b-环糊精。当用溴乙酸代替氯乙酸时，在较短的时间内得到二-o-羧甲基化b-环糊精。在二甲基甲酰胺溶液中，b-环糊精与氯乙酸甲酯和氢化钠反应，甲酯水解得到二-O-羧甲基化b-环糊精。二-o-羧甲基化b-环糊精与己二胺缩合反应得到分子量为10^4的聚酰胺。