Journal of Lipid Research, Vol 31, 2113-2117, Copyright © 1990 by Lipid Research, Inc.
Novel route to preparation of high purity lysoplasmenylethanolamine
DJ Hanahan, T Nouchi, ST Weintraub and MS Olson
Department of Biochemistry, University of Texas Health Science Center, San Antonio 78284-7760.
A rapid and simple method has been developed for the preparation of highly
purified lysoplasmenylethanolamine. The starting material, a
phosphatidylethanolamine (PE) sample that contained a mixture of the 1, 2
diacyl- and 1-O-alkenyl-2-acyl forms was subjected to mild alkaline
methanolysis for 20 min at room temperature. Addition of chloroform and
water with vigorous mixing, but without acidification at this point, led to
a preferential retention of the lysoplasmenylethanolamine in the alkaline
aqueous phase and complete separation of the methyl esters into the
chloroform phase. Neutralization of the alkaline phase with dilute acetic
acid, followed by addition of chloroform, allowed recovery of the
lysoplasmenylethanolamine in the chloroform phase in very high yields
(75-80% based on vinyl ether content of starting material). On the other
hand, a preparation of cholineglycerophospholipids enriched in
plasmenylcholine, treated in exactly the same manner, gave a
lysoplasmenylcholine that was not retained in the alkaline phase, but
partitioned primarily into the chloroform-rich phase together with the
methyl esters. Characterization of the purified lysoplasmenylethanolamine
was achieved by thin-layer chromatography and compositional analysis. In
addition, fast atom bombardment mass spectral analysis of the intact
lysoplasmenylethanolamine together with gas chromatography-mass
spectrometry of the dimethyl acetals derived from the 1-O-alkenyl chains
allowed further proof of the structure and an assessment of the purity of
this compound.
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