Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine

J Org Chem. 2022 Jun 17;87(12):8194-8197. doi: 10.1021/acs.joc.2c00335. Epub 2022 Jun 1.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Lysophosphatidylcholines* / chemistry
  • Lysophosphatidylcholines* / pharmacology
  • Phosphatidylcholines* / chemistry
  • Water

Substances

  • Lysophosphatidylcholines
  • Phosphatidylcholines
  • Water