1998 Fiscal Year Final Research Report Summary
Large Scale Preparation of Cyclodextrin Linked Chitin Derivatives Having Potential Use for Biological Friendly Host-compounds
| Project/Area Number |
09555290
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
高分子合成
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| Research Institution | HOKKAIDO UNIVERSITY |
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Principal Investigator |
SAKAIRI Nobuo Grad.School of Environ.EArth Sci., Hokkaido Univ., Pro., 大学院・地球環境科学研究科, 教授 (60153863)
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| Co-Investigator(Kenkyū-buntansha) |
SEINO Haruyoshi PIAS Cooporation, Bice Head Researcher, 第一事業本部, 副主任研究員
TOKURA Seiichi Faculty of Eng., Kansai Univ., Pro., 工学部, 教授 (40000806)
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| Project Period (FY) |
1997 – 1998
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| Keywords | Cyclodextrin / Chitosan / Chitin / Polysaccharide / inclusion complex / Controlled release |
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| Research Abstract |
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.
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