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Iterative Synthesis of Spacered Glycodendrons as Oligomannoside Mimetics and Evaluation of Their Antiadhesive Properties

机译:寡糖甘露糖苷模拟物的空间双缩糖双糖酮的迭代合成及其抗粘着性能的评价

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摘要

Dendrimer chemistry is an attractive concept for mimicry of the highly branched character of the bioac-tive carbohydrates found as part of a cell's sugar coat,called the glycocalyx.Glycodendrimers have thus been used to study biological processes occurring on cell surfaces,such as bacterial adhesion.This paper details a new approach in glycodendrimer synthesis,in which a 3,6-diallylated carbohydrate is utilised as core molecule,hydroboration-oxida-tion is the activating step,and glycosy-lation with branched and unbranched sugar trichloroacetimidates is used for dendritic growth.To obtain pure dendritic pseudo-tri-and-heptasaccharides in good yields,radical addition of mer-captoethanol to peripheral double bonds was also evaluated with great success.A collection of six new hyper-branched glycodendrons was tested for their potential as inhibitors of type 1 fimbriae-mediated bacterial adhesion in an ELISA and the results were interpreted with regard to sugar valency and spacer characteristics.
机译:树枝状大分子化学是模仿作为细胞糖衣的一部分被称为糖萼的生物活性碳水化合物的高度分支特性的一个引人注目的概念。因此,糖链分子被用于研究细胞表面发生的生物过程,例如细菌粘附本文详细介绍了糖树状大分子合成的一种新方法,该方法以3,6-二烯丙基化的碳水化合物为核心分子,硼氢化氧化为活化步骤,并用支链和直链糖三氯乙酰胺糖苷进行树突化。为了获得高收率的纯树突状伪三糖和七糖,还评估了将巯基乙醇自由基加成到周边双键上的成功方法。测试了六种新的超支化糖登花作为抑制剂的潜力。 ELISA中检测1型菌毛介导细菌粘附的方法,并就糖价和间隔子特性解释了结果抽动。

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