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...
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Published in | Tetrahedron Vol. 59; no. 16; pp. 2921 - 2928 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
14.04.2003
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | 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.
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/S0040-4020(03)00282-5 |