A convenient synthesis of phosphatidylcholines: acylation of sn-glycero-3-phosphocholine with fatty acid anhydride and 4-pyrrolidinopyridine.
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.
D000215:Acylation; D000812:Anhydrides; D005227:Fatty Acids; D005997:Glycerylphosphorylcholine; D008722:Methods; D010713:Phosphatidylcholines / Q000138:chemical synthesis*; D011725:Pyridines; D011759:Pyrrolidines
D000812:Anhydrides; D005227:Fatty Acids; D010713:Phosphatidylcholines; D011725:Pyridines; D011759:Pyrrolidines; C021249:4-pyrrolidinopyridine; D005997:Glycerylphosphorylcholine