Abstract
Rat-liver [ 32P]lecithin was hydrolyzed by snake venom phospholipase A to give quantitative yield of [ 32P]lysolecithins. The lysolecithins were oxidized in buffered aqueous solutions in the pH range 2.8 to 7.0, with bromine or permanganate to yield a keto-lysolecithin derivative. The extent and rate of oxidation is pH dependent. Bromine oxidation is more rapid at pH 6.8 than at pH 5.5 or 2.8. Permanganate oxidation is rapid at pH 5.5 but very slow at pH 6.8. During the oxidation partial concomitant hydrolysis occurs. The keto-lysolecithin can be separated and measured by paper chromatography and thus permits the determination of the α-lysolecithin isomer. The amount of this isomer was found to vary between 54–94% depending on the pH at which the bromine oxidation is carried out. Definitive evidence for the formation of the lysolecithinic acid has not yet been obtained. Passage of lysolecithin through silicic acid causes ester migration from the beta to the alpha position of glycerol. This is reflected by an increase in the keto-lysolecithin upon bromine oxidation. A novel reaction occurs when lysolecithin is treated with bromine in chloroform or methanol. Brominolysis rather than oxidation takes place with the formation of lysophosphatic acids and choline. A discussion of these findings is presented.
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