Scalable Synthesis and Purification of Acetylated Phosphatidyl Choline Headgroup.
Scalable Synthesis and Purification of Acetylated Phosphatidyl Choline Headgroup.
复制标题
乙酰化磷脂酰胆碱头基的可扩展合成和纯化。
DOI：
10.1021/acs.oprd.6b00261
复制
发表时间：
2017
影响因子：
3.4
通讯作者：
Balaz,Stefan
中科院分区：
文献类型：
--
作者：
Subramaniam,Rajesh;Jagadeesan,Ramesh;Mathew,Iswarya;Cen,Yana;Balaz,Stefan
哺乳动物中最丰富的磷脂--1，2-二乙酰基-3-sn-磷脂酰胆碱(DAcPC)的乙酰化头基在研究中有几个重要的应用。例如，它可以溶解在与流体PC双层中相同数量的水中，以生成PC头基层的替代品，用于研究小分子的溶剂化及其结构对过程的影响。与具有较长酰基链的PC衍生物相比，DAcPC不会自聚集，使水溶液均匀，适合简化分子与头基相互作用的分析。已经发表了几项研究，其中DAcPC以粗提纯的形式使用。在这里，我们描述了以市售原料药为原料一步法制备DAcPC，并通过结晶和洗涤提纯产品。该工艺的产率很高，而且很容易扩展。对映体、结晶DAcPC的可获得性可能为这种有趣的化学物质进行更广泛的生化、药理学和营养学研究打开大门。
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 the 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.