Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine

Lysophosphatidylcholine (LPC) and
phosphatidylcholine (PC) are
important membrane constituents implicated in signaling and immune
regulation. Synthesis of LPCs is challenging due to rapid acyl migration,
e.g., induced by chromatography. We here report a highly regioselective
synthesis of LPC and mixed PC via an intermediate allowing specific
terminal acyl introduction, yielding the pure LPC without chromatography
by an exceedingly mild TBS deprotection, using 1 equiv of TFA in aqueous
solution. The method enabled the synthesis of glycerol-, acyl-, and
choline-labeled LPC.