Synthesis of 1-lyso-2-palmitoyl-rac-glycero-3-phosphocholine and its regioisomers and structural elucidation by NMR spectroscopy and FAB tandem mass spectrometry |
| |
Authors: | Young-Ah KimMyoung-Soon Park Young Hwan Kim So-Yeop Han |
| |
Institution: | a Department of Chemistry, Division of Molecular Life Sciences, and Division of Nano Sciences, Ewha Womans University, Seoul 120-750, Republic of Korea b Proteome Analysis Team, Korea Basic Science Institute, Daejeon 305-806, Republic of Korea |
| |
Abstract: | 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. |
| |
Keywords: | 1-lysophosphatidylcholine acyl migration regioisomer NMR (nuclear magnetic resonance) FAB-MS (fast atom bombardment mass spectrometry) MS/MS (tandem mass spectrometry) CID (collision-induced dissociation) |
本文献已被 ScienceDirect 等数据库收录! |