Journal of Lipid Research, Vol 20, 674-677, Copyright © 1979 by Lipid Research, Inc.

ARTICLES

A convenient synthesis of phosphatidylcholines: acylation of sn-glycero- 3-phosphocholine with fatty acid anhydride and 4-pyrrolidinopyridine

KM Patel, JD Morrisett and JT Sparrow

A high-yield synthesis of saturated, unsaturated, and short chain phosphatidylcholines from sn-glycero-3-phosphocholine is described. The procedure offers advantages over other reported procedures for the synthesis of phosphatidylcholine in that the large-scale synthesis and purification can be achieved in a minimum time. The procedure utilizes 4-pyrrolidinopyridine as a catalyst and moderate amounts of fatty acid anhydride (2 mol eq. of fatty acid anhydride per mol of OH) in a 1:1 mixture of benzene-dimethylsulfoxide (DMSO) at 40 degrees--42 degrees C (oilbath) for 2--5 hr. At the end of the reaction, the phosphatidylcholine can be purified in the usual manner or by using a Waters Prep LC/500 with a radially compressed silica gel column eluted with chloroform-methanol-water 60:30:4. At a flow rate of 200 ml/min, the phospholipid elutes in 10--15 min, depending on the chain length and unsaturation.
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