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An improved procedure for the synthesis of choline phospholipids via 2‐bromoethyl dichlorophosphate
Author(s) -
Hansen William J.,
Murari Ramaswamy,
Wedmid Yuri,
Baumann Wolfgang J.
Publication year - 1982
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02535226
Subject(s) - chemistry , trimethylamine , choline , nucleophile , phosphocholine , organic chemistry , alcohol , diol , alkoxy group , phosphatidylcholine , nuclear magnetic resonance spectroscopy , ether , phospholipid , alkyl , catalysis , biochemistry , membrane
Choline phospholipids can be conveniently synthesized by reaction of a lipophilic alcohol, such as diacylglycerol, with 2‐bromoethyl dichlorophosphate followed by nucleophilic displacement of the bromine with trimethylamine. We found that the low yields often encountered in the initial phosphorylation step are particularly due to exchange of both chlorines for alkoxy functions (triester formation) and to chlorination of the alcohol by 2‐bromoethyl dichlorophosphate. However, these drawbacks can be overcome by proper choice of the reaction medium and by optimizing other reaction conditions. The procedure described is efficient and most versatile, and it lends itself to the preparation of a wide range of choline phospholipids containing a glycerol, diol, or long‐chain alkyl backbone and bearing various aliphatic functions. Proton and carbon‐13 nuclear magnetic resonance spectroscopy proved useful in establishing the homogeneity and structures of the synthetic intermediates and byproducts and of the choline phospholipids synthesized.