Journal of Lipid Research, Vol 29, 384-388, Copyright © 1988 by Lipid Research, Inc.
Quantitative conversion of diether or tetraether phospholipids to glycerophosphoesters by dealkylation with boron trichloride: a tool for structural analysis of archaebacterial lipids
M Nishihara and Y Koga
Department of Chemistry, University of Occupational and Environmental Health, Kitakyushu, Japan.
A method for preparing glycerophosphoesters from ether phospholipids by
dealkylation with boron trichloride (BCl3) is described. Treatment of ether
phospholipids in chloroform with BCl3 for 30 min at room temperature
yielded almost quantitatively the corresponding glycerophosphoesters
retaining the intact polar head group of the ether phospholipids. Thus,
glycerophosphocholine, glycerophosphoinositol, glycerophosphoglycerol,
glycerophosphoserine, glycerophosphate, and glycerophosphoethanolamine were
prepared from the diether analogs of phosphatidylcholine,
phosphatidylinositol, phosphatidylglycerol, phosphatidylserine, and
phosphatidic acid, and the tetraether analog of phosphatidylethanolamine,
respectively. BCl3 also cleaved diacyl, alkyl- acyl, and alk-1-enyl-acyl
forms of phospholipids to yield corresponding glycerophosphoesters. The
glycerophosphoesters were separated more rapidly by cellulose thin-layer
chromatography with the same solvent system as in paper chromatography.
This method is of great use for structure determination of
glycerophosphoester backbones of ether phospholipids, analogous to the mild
alkaline methanolysis of diacyl form of phospholipids, as well as for the
analysis of alkyl chains. It is, however, not applicable to glycolipids
because of cleavage of glycosidic bonds by BCl3.
CiteULike 
Complore 
Connotea 
Del.icio.us 
Digg 
Reddit 
Technorati What's this?
