title: Synthesis and proaggregatory activity of 1-O-(2-methyloctadecyl)-2-O-acetyl-rac-glycero-3-phosphocholine.
abstract: Racemic 1-O-(2-methyloctadecyl)-2-O-acetyl-glycero-3-phosphocholine, a branched chain PAF species, was prepared by chemical synthesis and investigated for biological activity on human blood platelets in vitro. The synthesis started from 2-O-benzylglycerol and 2-methyloctadecyl-1-methyl sulfonate and was accomplished in five reaction steps. A comparison with 'octadecyl-rich' PAF showed that the PAF species described here exerts a 22-fold weaker proaggregatory activity. Based on [3H]PAF-binding studies, an obstruction of PAF-binding or the signal transduction by the branched alkyl chain in C-1 position of the glycerol backbone is suggested.
authors.affiliation: Medizinische Akademie, Institut für Pathologische Biochemie, Erfurt, F.R.G.
authors.forename: B
authors.initials: B
authors.lastname: Schmid
authors.forename: G
authors.initials: G
authors.lastname: Ostermann
authors.forename: H P
authors.initials: HP
authors.lastname: Kertscher
mesh_terms: D006801:Humans; D015394:Molecular Structure; D010972:Platelet Activating Factor / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D010974:Platelet Aggregation / Q000187:drug effects*; D011485:Protein Binding
chemical_list: D010972:Platelet Activating Factor; C074571:1-O-(2-methyloctadecyl)-2-O-acetyl-rac-glycero-3-phosphocholine