A simple chemical synthesis of the ether analog of lysophosphatidylcholine and platelet-activating factor.
作者： A K Das , A K Hajra
DOI: 10.1016/S0022-2275(20)39727-3
关键词: Phosphocholine 、 Chemical synthesis 、 Alkyl 、 Hydrolysis 、 Lysophosphatidylcholine 、 Ether 、 Chemistry 、 Phosphorolysis 、 Organic chemistry 、 Platelet-activating factor
摘要: A simple chemical procedure for synthesis of 1-O-alkyl-(rac or sn)-glycero-3-phosphocholine (alkyl analog lysophosphatidylcholine, II) and platelet activating factor (PAF), 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (III) has been described. The key step the method is decomposition 1-O-hexadecyl-3-diazohydroxyacetone (A. K. Hajra, T. V. Saraswathi A. Das, 1983. Chem. Phys. Lipids. 33: 179-193) with phosphocholine to synthesize 1-O-hexadecyl dihydroxyacetone-3-phosphocholine (I). Conditions this phosphorolysis were studied respect reaction medium, temperature, optimum proportion reactants. Compound (I) was quantitatively reduced NaBH4 (II) which acetylated prepare compound (III). Phospholipase A2 hydrolysis followed by separation products afforded unreacted sn-3-hexadecyl isomer sn-1-hexadecyl PAF. structures compounds verified NMR FAB-MS spectra, their biological activities determined measuring release serotonin from rabbit blood platelets in response different doses these compounds. suitability as a general technique ether phosphoglycerides discussed.
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