Journal
TETRAHEDRON
Volume 59, Issue 16, Pages 2921-2928Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(03)00282-5
Keywords
l-lysophosphatidylcholine; acyl migration; regioisomer; NMR (nuclear magnetic resonance); FAB-MS (fast atom bombardment mass spectrometry); MS/MS (tandem mass spectrometry); CID (collision-induced dissociation)
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Three regioisomers of a naturally occurring lysophosphatidylcholine were chemically synthesized from glycerol. The phosphocholine moiety of the molecule was introduced by sequentially reacting with ethylene chlorophosphite, bromine, water, and trimethyl amine. Removal of a silyl protecting group of the hydroxyl group in the glycerol backbone was achieved without any accompanying acyl migration in the final stage of the synthesis by using NBS in a dimethyl sulfoxide-water cosolvent system. Structures of all regioisomers were compared by NMR spectroscopy and FAB tandem mass spectrometry. (C) 2003 Elsevier Science Ltd. All rights reserved.
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