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Scalable Synthesis and Purification of Acetylated Phosphatidyl Choline Headgroup

机译:乙酰化磷脂酰胆碱头基的可扩展合成与纯化

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摘要

The acetylated headgroup of the most abundant mammalian phospholipid, 1,2-diacetyl-3-sn-phosphatidyl choline (DAcPC), has several important applications in research. For instance, it can be dissolved in the same amount of water as in the fluid PC bilayer, to create a surrogate of a PC headgroup stratum, for studying solvation of small molecules and the influence of their structure on the process. In contrast to PC derivatives with longer acyl chains, DAcPC does not self-aggregate, rendering the aqueous solution homogeneous and suitable for simplified analyses of interactions of molecules with the headgroups. Several studies have been published where DAcPC was used in a crudely purified form. Here we describe a one-step preparation of DAcPC from commercially available bulk chemicals and purification of the product by crystallization and washing. The process gives a good yield and is easily scalable. The availability of enantiopure, crystalline DAcPC could open the door to more extensive biochemical, pharmacological, and nutritional studies of this interesting chemical.
机译:最丰富的哺乳动物磷脂1,2,2-二乙酰基-3-sn-磷脂酰胆碱(DAcPC)的乙酰化头基在研究中有几个重要应用。例如,可以将其溶解在与PC双层流体相同的水中,以形成PC头基层的替代物,以研究小分子的溶剂化及其结构对工艺的影响。与具有较长酰基链的PC衍生物相反,DAcPC不会自聚集,从而使水溶液均匀且适合于简化分子与头基的相互作用分析。已经发表了一些研究,其中以粗纯化形式使用DAcPC。在这里,我们描述了从市售散装化学品中一步制备DAcPC的方法,以及通过结晶和洗涤纯化产品的步骤。该方法收率良好,易于扩展。对映纯的结晶DAcPC的可用性可以为这种有趣的化学物质的更广泛的生化,药理和营养研究打开大门。

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