Efficient synthesis of the cholinephosphate phospholipid headgroup

被引：4

作者：

Hendrickson, EK ^{[1
]}

Hendrickson, HS ^{[1
]}

机构：

[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 2001年 / 109卷 / 02期

基金：

美国国家科学基金会;

关键词：

2-bromoethanol; cholinephosphate; hexadecylphosphocholine; phosphatidylcholine; phosphite triester; phospholipid; synthesis; phosphoryl iodide;

D O I：

10.1016/S0009-3084(00)00224-3

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In search of an efficient method to prepare cholinephosphate headgroups in phospholipids under mild conditions (where the diacylglycerol moiety is not subject to oxidation), a method was developed For phosphorylation using a trialkyl phosphite and I,. The active intermediate is a phosphoryl iodide formed by oxidation of the phosphite with I-2. 2-Bromoethanol, dimethyl chlorophosphite, and an alcohol (diglyceride) are converted to a phosphate triester in a one-pot reaction with high yield. In the second reaction, the phosphate triester is demethylated, and the ethyl bromide group is converted to choline by treatment with aqueous trimethylamine. This procedure is applied to the synthesis of hexadecylphosphocholine, and 1,2-didecanoyl-1 -deoxy-1-thio-sn-glyceryo-3-phosphocholine. (C) 2001 Published by Elsevier Science Ireland Ltd.

引用

页码：203 / 207

页数：5

共 16 条

[1] ADVANCES IN THE SYNTHESIS OF OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH [J].