Facile synthesis of branched chitin by glycosylation of fully trimethylsilylated chitin with a glucosamine-derived oxazoline |
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Authors: | Kazuhiro Sugita Yuhki Tanabe Naoki Kodaira Masaaki Hirakawa Shohko Yamaguchi Asuka Shibata Manabu Shimojoh Keisuke Kurita |
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Affiliation: | 1. Department of Materials and Life Science, Faculty of Science and Technology, Seikei University, Musashino-shi, Tokyo, 180-8633, Japan 2. Research and Development Center, Toyo Suisan Kaisha, Ltd., Shiohama, Koto-ku, Tokyo, 135-0043, Japan
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Abstract: | A simple and straightforward procedure for synthesizing branched chitin and chitosan has been developed on the basis of the glycosylation of trimethylsilylated chitin with an oxazoline derived from d-glucosamine. Chitin was first trimethylsilylated, and the derivative was treated with the oxazoline to introduce peracetylated d-glucosamine branches into the chitin backbone. The extent of branching was dependent on the amount of the oxazoline and reaction time, and under appropriate conditions, it reached around 0.65. Selective O-deacetylation or thorough N,O-deacetylation of the resulting glycosylated product gave chitin having N-acetyl-d-glucosamine branches or chitosan having d-glucosamine branches. |
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