Faculty Collaboration Database

Facile synthesis of platelet-activating factor and racemic analogues containing unsaturation in the sn-1-alkyl chain. J Med Chem 1985 Jan;28(1):73-8

Date

01/01/1985

Pubmed ID

4038418

DOI

10.1021/jm00379a015

Scopus ID

2-s2.0-0021947934 (requires institutional sign-in at Scopus site)   58 Citations

Abstract

Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.

Author List

Surles JR, Wykle RL, O'Flaherty JT, Salzer WL, Thomas MJ, Snyder F, Piantadosi C

MESH terms used to index this publication - Major topics in bold

Animals
Blood Platelets
Blood Pressure
Magnetic Resonance Spectroscopy
Mice
Neutrophils
Platelet Activating Factor
Rabbits
Rats
Rats, Inbred SHR
Serotonin