Chemoselective protection of the amino groups of chitosan by controlled phthaloylation: Facile preparation of a precursor useful for chemical modifications

被引:233
作者
Kurita, K [1 ]
Ikeda, H
Yoshida, Y
Shimojoh, M
Harata, M
机构
[1] Seikei Univ, Fac Engn, Dept Appl Chem, Musashino, Tokyo 1808633, Japan
[2] Toyo Suisan Kaisha Ltd, Dept Res & Dev, Minato Ku, Tokyo 1088501, Japan
关键词
D O I
10.1021/bm0101163
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A simple and convenient procedure for chemos electively protecting the amino groups of chitosan has been developed to provide N-phthaloyl-chitosan that is indispensable as a soluble N-protected precursor for further controlled modification reactions of chitosan. Although the conventional N-phthaloylation of chitosan in N,N-dimethylformamide was accompanied by partial phthaloylation of the hydroxy groups, the addition of a small amount of hydroxy-containing compounds effectively suppressed the O-phthaloylation. Of some compounds examined, water proved particularly suitable, resulting in the formation of chemoselectively N-phthaloylated chitosan without any appreciable O-phthaloyl groups. The resulting N-phthaloyl-chitosan was found to be crystalline despite the presence of a bulky substituent. A solubility test indicated that N-phthaloyl-chitosan exhibited considerable affinity for organic solvents.
引用
收藏
页码:1 / 4
页数:4
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