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Large Scale Preparation of Cyclodextrin Linked Chitin Derivatives Having Potential Use for Biological Friendly Host-compounds

大规模制备环糊精连接的甲壳质衍生物，具有生物友好性主体化合物的潜在用途

基本信息

批准号：
09555290
负责人：
SAKAIRI Nobuo
金额：
$ 3.9万
依托单位：
HOKKAIDO 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 1998
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-09555290/
关键词：
Cyclodextrin Chitosan Chitin Polysaccharide inclusion complex Controlled release 包接剤

项目摘要

Novel polysaccharide derivatives capable of forming inclusion complexes with various organic compounds have been synthesized by coupling chitosan with cyclodextrins. Chitosan is an amino-polysaccharide prepared by de-N-acetylation of chitin, a major component of crab shell, and cyclodextrin is a cyclic oligomer of alpha-(l, 4)-linked glucose. In the present study, reductive amination of (formylmethyl)-cyclodextrins was found useful for the coupling with chitosan. This method was applicable to the synthesis of high molecular weight (>250,000) cyclodextrin-linked chitosan in a homogeneous reaction system. The degree of substitution (D.S.) varied from 7 to 75% depending on the amount of the starting cyclodextrin derivative used. Derivatives with D.S.>30% were soluble in water under neutral or alkaline conditions. Preliminary spectroscopic analyses using model guest compounds suggested that their ability to form inclusion complexes (as measured by their dissociation constants) was almost the identical with that of the uncoupled cyclodextrin. Furthermore, insoluble cyclodextrin-linked chitosan with a highly porous structure was prepared by a similar coupling method using cross-linked chitosan beads. Preliminary experiments were conducted to assess the utility of these polymeric host compounds for reversed-phase chromatography, as adsorbents for controlled release applications, as a pseudostationary phase in capillary electrophoresis, and as additives in cosmetics to protect skin from chemical damage. N-acetylation of the resulting cyclodextrin linked chitosan with acetic anhydride in water gave cyclodextrin-linked chitin in almost quantitative yield.

通过壳聚糖与环糊精的偶联，合成了新型的多糖衍生物，它们能与多种有机化合物形成包合物。壳聚糖是通过甲壳素（蟹壳的主要成分）的脱N-乙酰化制备的氨基多糖，环糊精是α-（1，4）-连接的葡萄糖的环状低聚物。在本研究中，（甲酰基甲基）-环糊精的还原胺化被发现有用的偶联与壳聚糖。该方法适用于在均相反应体系中合成高分子量（> 25万）环糊精连接壳聚糖。取代度（D.S.）取决于所用的起始环糊精衍生物的量，从7至75%变化。衍生物与D.S.> 30%在中性或碱性条件下溶于水。初步的光谱分析，使用模型客体化合物表明，他们的能力，形成包合物（由其解离常数测量）是几乎相同的与未偶联的环糊精。此外，不溶性的环糊精连接的壳聚糖具有高度多孔结构的制备通过类似的耦合方法使用交联壳聚糖珠。进行了初步的实验，以评估这些聚合物的主体化合物的效用为反相色谱，作为吸附剂的控制释放应用，作为伪固定相在毛细管电泳，并作为化妆品中的添加剂，以保护皮肤免受化学损伤。在水中用乙酸酐将所得环糊精连接的壳聚糖N-乙酰化，得到几乎定量产率的环糊精连接的甲壳素。