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

• Published in: Tetrahedron Vol. 59; no. 16; pp. 2921 - 2928
• Main Authors: Kim, Young-Ah, Park, Myoung-Soon, Kim, Young Hwan, Han, So-Yeop
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 14.04.2003; Elsevier
• Subjects: 1-lysophosphatidylcholine; acyl migration; Chemistry; Chemistry, Organic; CID (collision-induced dissociation); FAB-MS (fast atom bombardment mass spectrometry); MS/MS (tandem mass spectrometry); NMR (nuclear magnetic resonance); Physical Sciences; regioisomer; Science & Technology; regioisomer; 1-lysophosphatidylcholine; CID (collision-induced dissociation); MS/MS (tandem mass spectrometry); acyl migration; FAB-MS (fast atom bombardment mass spectrometry); NMR (nuclear magnetic resonance); CELLS; ACID; STEREOSPECIFIC SYNTHESIS; ETHER PHOSPHOLIPIDS; FATTY ACYL-GROUPS; MONOACETYLDIGLYCERIDES; LYSOPHOSPHATIDYLCHOLINE; l-lysophosphatidylcholine; BOVINE UDDER; PLATELET-ACTIVATING-FACTOR; BRAIN
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(03)00282-5

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. Graphic