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
01/01/1985Pubmed ID
4038418DOI
10.1021/jm00379a015Scopus ID
2-s2.0-0021947934 (requires institutional sign-in at Scopus site) 58 CitationsAbstract
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 CAuthor
Michael J. Thomas PhD Professor in the Pharmacology and Toxicology department at Medical College of WisconsinMESH terms used to index this publication - Major topics in bold
AnimalsBlood Platelets
Blood Pressure
Magnetic Resonance Spectroscopy
Mice
Neutrophils
Platelet Activating Factor
Rabbits
Rats
Rats, Inbred SHR
Serotonin