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首页> 外文期刊>Chemistry: A European journal >Synthesis and Molecular Tumbling Properties of Sialyl Lewis X and Derived Neoglycolipids
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Synthesis and Molecular Tumbling Properties of Sialyl Lewis X and Derived Neoglycolipids

机译：唾液酸化的路易斯X和衍生的新糖脂的合成及其分子翻转特性

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摘要

The sialyl Lewis X (sLe~X) epitope has become a prominent target for biological studies because of its role in inflammation through binding to selectins. This epitope is located as the terminal end in glycosphingolipids and a lactose unit serives as spacer to the ceramide moiety. This paper focuses on the influence of the spacer structure and spacer length is regard to the mobilithy of the SLx~X epitope. To this end sLe~X neoglycolipids 1a-c, with one, two, or three lactose units as spacer between the sLx~X tetrasaccharide epitope and the membrane anchor, were synthesized. The synthetic strategy was also applied to the syntheiss of the corresponding Lewis X(Le~X) derivatives. The glycolipids were inserted in model membranes, and the tumblinmg frequencies of the sLe~X tetrasaccharide epitopes were then analysed by NMR spectroscopy. A nonathlene glycol spacer decouples the carbohydrate moiety from the membarne mobility while (oligo-)lactoses act as more rigid distance keepers between the Lewis epitope and the surafce of the membrane. Quantification of the different degrees of decoupling was possibile by analysis of rotational correlation times.
机译：唾液酸化的路易斯X（sLe〜X）表位已成为生物学研究的主要目标，因为它通过与选择素结合而在炎症中发挥作用。该表位位于糖鞘脂的末端，而乳糖单元作为神经酰胺部分的间隔基。本文着重于间隔子结构的影响，间隔子的长度与SLx〜X表位的运动性有关。为此，合成了具有一个，两个或三个乳糖单元作为sLx〜X四糖表位和膜锚之间的间隔基的sLe〜X新糖脂1a-c。该合成策略还应用于相应的Lewis X（Le〜X）衍生物的合成。将糖脂插入模型膜中，然后通过NMR光谱分析sLe〜X四糖表位的摆动频率。九碳烯间隔基使碳水化合物部分与膜的运动性脱钩，而（低聚）乳糖酶则充当路易斯表位与膜表面之间更牢固的距离保持物。通过分析旋转相关时间，可以对不同程度的解耦进行定量。

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