Synthesis of 1-lyso-2-palmitoyl-rac-glycero-3-phosphocholine and its regioisomers and structural elucidation by NMR spectroscopy and FAB tandem mass spectrometry

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.