Carbosilane Dendrimers Bearing Globotriaoses: Construction of a Series of Carbosilane Dendrimers Bearing Globotriaoses

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• 作者：Koji Matsuoka ; Mikiko Terabatake ; Yasuaki Esumi ; Ken Hatano ; Daiyo Terunuma ; Hiroyoshi Kuzuhara
• 刊名：Biomacromolecules
• 出版年：2006
• 出版时间：August 2006
• 年：2006
• 卷：7
• 期：8
• 页码：2284 - 2290
• 全文大小：216K
• 年卷期：v.7,no.8(August 2006)
• ISSN：1526-4602

文摘

To enhance biological activities on the basis of the sugar cluster effect, a series of carbosilane dendrimers as corescaffolds for the construction of glycodendrimers was systematically synthesized from appropriate chlorosilanesby a combination of alkenylation and hydrosylation reactions. Those carbosilane dendrimers having terminalC=C double bonds underwent general hydroboration reactions to give corresponding primary polyols. Furthertransformations of the alcohols were then performed by mesylation followed by a displacement with NaBr toprovide corresponding dendrimers with 4 to 36 bromine atoms at each terminal end. Assembly of trisaccharidemoieties of globotriaosyl ceramide using alkyl halide-type carbosilane dendrimers as the core frame was conductedin liquid ammonia by a one-pot reaction involving selective removal of a benzyl group under the Birch reductioncondition and subsequent S_N2 reaction to yield a series of carbosilane dendrimers having appropriate numbers oftrisaccharide moieties. These dendrimers have unique shapes and adequate numbers of terminal trisaccharidemoieties. Some of the dendrimers showed unique biological activity against Stxs, which were produced bypathogenic Escherichia coli O157:H7.