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

Title
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
Kim Y.-A.Park M.-S.Kim Y.H.Han S.-Y.
Ewha Authors
한소엽
SCOPUS Author ID
한소엽scopus
Issue Date
2003
Journal Title
Tetrahedron
ISSN
0040-4020JCR Link
Citation
vol. 59, no. 16, pp. 2921 - 2928
Indexed
SCI; SCIE; SCOPUS WOS scopus
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. © 2003 Elsevier Science Ltd. All rights reserved.
DOI
10.1016/S0040-4020(03)00282-5
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자연과학대학 > 화학·나노과학전공 > Journal papers
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