Preparation of labeled alkyl acyl glycerophosphorylcholine

A Poulos

doi:10.1016/s0022-2275(20)42960-8

Abstract

A method for the preparation of 1-alkyl 2-acyl glycero-3-phosphorylcholine, labeled in the 2-position with oleic acid-1-(14)C is described. This method, based on the acylation of a 1-alkyl glycero-3-phosphorylcholine-CdCl(2) complex which is, in turn, formed from 1-alk-1-enyl glycero-3-phosphorylcholine by hydrogenation and subsequent reaction with cadmium chloride, offers a relatively simple means of preparing a labeled saturated ether phospholipid suitable for use in metabolic studies.

Highlights

I t is the purpose of this paper to describe a method for thc preparation of a radioactive alkyl acyl phospholipid which is convenient, rapid, and does not require the use of unfamiliar intermediates
The method is based on the acylation of the cadmium chloride complex of 1-alkyl glycero3-phosphorylcholine which is in turn derived from the alkaline hydrolysis of ox heart lecithin
The alkali-stable lipid (89 pmoles of aldehyde) in 10 ml of chloroform-methanol 1:1 was applied to a column of silicic acid (8 g, 24 X 1 cm) in the same solvent mixture. 150 ml of chloroform-methanol 1:1 and 250 ml of chloroform-methanol 2 :5 were passed through the column. 10-ml fractions were collected automatically at a rate of 1.5 nil/min, and were monitored by TLCin chloroform-methanol-35~o ammonia 70 :30

Summary

Introduction

The method is based on the acylation of the cadmium chloride complex of 1-alkyl glycero3-phosphorylcholine which is in turn derived from the alkaline hydrolysis of ox heart lecithin (mixture of phosphatidyl- and phosphatidalcholine) . Further purification of the phospholipid fraction was achieved by streaking samples (55 fig-atoms of lipid phosphorus) on washed, activated plates of ncutral silica gel (20 X 20 cm, 500 p thick) and by developing chromatograms in chloroform-methanol-35~o animonia 70 :30 :S(v/v/v). The alkali-stable lipid (89 pmoles of aldehyde) in 10 ml of chloroform-methanol 1:1 was applied to a column of silicic acid (8 g, 24 X 1 cm) in the same solvent mixture.

Results

Conclusion