Synthesis of mixed-acid phosphatidylcholines and high pressure liquid chromatographic analysis of isomeric lysophosphatidylcholines.
Synthesis of mixed-acid phosphatidylcholines and high pressure liquid chromatographic analysis of isomeric lysophosphatidylcholines.
复制标题
混合酸磷脂酰胆碱的合成和异构溶血磷脂酰胆碱的高压液相色谱分析。
作者：
Nicholas,AW;Khouri,LG;EllingtonJr,JC;Porter,NA
报道了一种合成混合链磷脂酰胆碱的新方法。银离子催化的 2-硫代吡啶酯对溶血磷脂酰胆碱的酰化在室温下在有机溶剂中快速发生（10 分钟）。异构纯混合链磷脂酰胆碱（异构体纯度>98%）的产率通常大于80%。该反应仅用 1.5 至 2 倍过量的硫代吡啶酯进行，因此在使用珍贵的酰化剂时比现有方法具有一些优势。该程序的主要缺点是对水敏感。具有羟基脂肪酰基的磷脂酰胆碱是通过将羟基保护为乙酰丙酸酯、转化为2-硫代吡啶酯、酰化并用肼除去乙酰丙酸酯来制备的。为了纯化溶血磷脂酰胆碱，开发了一种用于分离 1-酰基甘油磷酸胆碱和 2-酰基甘油磷酸胆碱的反相高压液相色谱方法。
A new method for the synthesis of mixed‐chain phosphatidylcholines is reported. Silver ion catalyzed acylation of lysophosphatidylcholines by 2‐thiopyridyl esters occurs rapidly (10 min) at room temperature in organic solvents. Yields of isomerically pure mixed‐chain phosphatidylcholines (>98% isomeric purity) are generally greater than 80%. The reaction proceeds with only 1.5‐ to 2‐fold excess of thiopyridyl ester, thus offering some advantages over existing procedures when precious acylating agents are used. The major disadvantage of the procedure is its sensitivity to water. Phosphatidylcholines having hydroxy fatty acyl groups are prepared by protection of the hydroxyl as the levulinate ester, conversion to the 2‐thiopyridyl ester, acylation, and removal of the levulinate with hydrazine. For purification of lysophosphatidylcholines, a reverse‐phase high pressure liquid chromatographic method for separation of 1‐acylglycerophosphocholines from 2‐acylglycerophosphocholines was developed.