caa a22 4500 465766250 CHVBK 20180323111914.0 cr unu---uuuuu 170327e19901001xx s 000 0 eng 10.1007/BF02536010 doi (NATIONALLICENCE)springer-10.1007/BF02536010 Lyso platelet activating factor (LysoPAF) and its enantiomer. Total synthesis and carbon-13 NMR spectroscopy [Elektronische Daten] [M. Murari, R. Murari, S. Parthasarathy, C. Guy, V. Kumar, B. Malewicz, Wolfgang Baumann] Described is a reaction sequence for the total synthesis of lyso platelet activating factor (lysoPAF; 1-O-alkyl-sn-glycero-3-phosphocholine) and its enantiomer. The procedure is versatile and yields optically pure isomers of defined chain length. The synthesis is equally suited for the preparation of lysoPAF analogues and its enantiomers with unsaturation in the long aliphatic chain. First,rac-1(3)-O-alkylglycerol is prepared by alkylation ofrac-isopropylideneglycerol with alkyl methanesulfonate followed by acid-catalyzed removal of the ketal group. The primary hydroxy group of alkylglycerol is then protected by tritylation, the secondary hydroxy group is acylated, and the protective trityl group is removed under mild acidic conditions with boric acid on silicic acid, essentially without acyl migration. Condensation of the diradylglycerol with bromoethyl dichlorophosphate in diethyl ether, hydrolysis of the resulting chloride, and nucleophilic displacement of the bromine with trimethylamine givesrac-1-O-alkyl-2-acylglycero-3-phosphocholine in good overall yield. The racemic alkylacylglycerophosphocholine is finally treated with snake venom phospholipase A2 (Ophiophagus hannah) which affords 1-O-alkyl-sn-glycero-3-phosphocholine (lysoPAF) of natural configuration in optically pure form. The "unnatural” 3-O-alkyl-2-O-acyl-sn-glycerol-1-phosphocholine enantiomer, which is not susceptible to phospholipase A2 cleavage, gives 3-O-alkyl-sn-glycero-1-phosphocholine upon deacylation with methanolic sodium hydroxide. Homogeneity and structure of the intermediates and final products were ascertained by carbon-13 nuclear magnetic resonance spectroscopy on monomeric solutions. American Oil Chemists' Society, 1990 Murari M. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut Murari R. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut Parthasarathy S. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut Guy C. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut Kumar V. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut Malewicz B. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut Baumann Wolfgang Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut Lipids Springer-Verlag 25/10(1990-10-01), 606-612 0024-4201 25:10<606 1990 25 11745 https://doi.org/10.1007/BF02536010 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02536010 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Murari M. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut NATIONALLICENCE 700 1- Murari R. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut NATIONALLICENCE 700 1- Parthasarathy S. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut NATIONALLICENCE 700 1- Guy C. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut NATIONALLICENCE 700 1- Kumar V. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut NATIONALLICENCE 700 1- Malewicz B. Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut NATIONALLICENCE 700 1- Baumann Wolfgang Section of Bio-Organic Chemistry, The Hormel Institute, University of Minnesota, 55912, Austin, Minnesota aut NATIONALLICENCE 773 0- Lipids Springer-Verlag 25/10(1990-10-01), 606-612 0024-4201 25:10<606 1990 25 11745 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer