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Design and synthesis of glycodendrimers

机译:糖树状聚合物的设计与合成

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Multivalent neoglycoconjugates with well-defined structures have considerable potential as inhibitors of cell surface protein-carbohydrate interactions and as tools for studying such recognition processes in vitro. In this review, we outline strategies and synthetic methods for making one such class of neoglycoconjugates based on dendrimers - the so-called glycodendrimers. Glycodendrimers can be classified as: (i) carbohydrate-coated; (ii) carbohydrate-centered; and (iii) fully carbohydrate-based. Approaches to their construction have included both the modification of commercially available dendrimers and de novo dendrimer synthesis. Examples from the authors' and other laboratories are drawn upon to illustrate design considerations and the application of dendritic synthetic principles - including divergent and convergent syntheses - for making glycodendrimers. Key coupling reactions for the synthesis of glycodendrimers include: amide and thiourea formation; glycosylation; photoaddition to allyl ethers; and reductive amination. The advantages and disadvantages of using protected and unprotected saccharide building blocks and potential applications for glycodendrimers in both biotechnology and materials science are also discussed.
机译:具有明确结构的多价新糖缀合物具有作为细胞表面蛋白与碳水化合物相互作用的抑制剂和作为体外研究此类识别过程的工具的巨大潜力。在这篇综述中,我们概述了基于树枝状大分子(所谓的糖类树枝状大分子)制备一类此类新糖缀合物的策略和合成方法。糖基糖精可以归类为:(i)糖衣包被的; (ii)以碳水化合物为中心; (iii)完全基于碳水化合物。构建它们的方法既包括商业上可获得的树枝状聚合物的修饰,也包括从头开始的树枝状聚合物的合成。引用作者和其他实验室的实例来说明设计考量和树突状合成原理(包括发散和会聚合成)在制备糖类树状大分子中的应用。糖基树状大分子合成的关键偶联反应包括:酰胺和硫脲的形成;糖基化与烯丙基醚光加成;和还原胺化。还讨论了在生物技术和材料科学中使用受保护和不受保护的糖结构单元的优缺点以及糖树状聚合物的潜在应用。

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