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Synthesis and proaggregatory activity of 1-O-(2-methyloctadecyl)-2-O-acetyl-rac-glycero-3-phosphocholine

✍ Scribed by B. Schmid; G. Ostermann; H.-P. Kertscher

Publisher: Elsevier Science
Year: 1991
Tongue: English
Weight: 344 KB
Volume: 60
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(91)90017-6

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✦ Synopsis

Racemic l-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-l-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-I position O f the glycerol backbone is suggested.

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