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

被引：23

作者：

Kim, YA

Park, MS

Kim, YH

Han, SY ^{[1
]}

机构：

[1] Korea Basic Sci Inst, Proteome Anal Team, Taejon 305806, South Korea

[2] Ewha Womans Univ, Dept Chem, Div Mol Life Sci, Seoul 120750, South Korea

[3] Ewha Womans Univ, Div Nano Sci, Seoul 120750, South Korea

[4] Korea Basic Sci Inst, Proteome Anal Team, Taejon 305806, South Korea

来源：

TETRAHEDRON | 2003年 / 59卷 / 16期

关键词：

l-lysophosphatidylcholine; acyl migration; regioisomer; NMR (nuclear magnetic resonance); FAB-MS (fast atom bombardment mass spectrometry); MS/MS (tandem mass spectrometry); CID (collision-induced dissociation);

D O I：

10.1016/S0040-4020(03)00282-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

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.

引用

页码：2921 / 2928

页数：8

共 37 条

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ROLE OF LYSOPHOSPHATIDYLCHOLINE IN LYMPHOCYTE-T ACTIVATION - INVOLVEMENT OF PHOSPHOLIPASE-A2 IN SIGNAL TRANSDUCTION THROUGH PROTEIN-KINASE-C [J].