An Effective Method for the Evaluation of the Enantiomeric Purity of 1,2-Diacyl-<i>sn</i>-glycero-3-phosphocholine-Based Lipids by NMR Analysis

oleh: Antonia Di Mola, Lorenzo de Ferra, Mauro Anibaldi, Guglielmo Monaco, Antonio Massa

Format: Article
Diterbitkan: MDPI AG 2024-05-01

Deskripsi

In this article, we report a very efficient method for the determination of the enantiopurity of 1,2-diacyl-<i>sn</i>-glycero-3-phosphocholine by <sup>1</sup>H NMR analysis using a readily available chiral derivatizing boronic acid (CDA), (<i>R</i>)-(2-(((1-phenylethyl)amino)methyl)phenyl)boronic acid. After the removal of the acyl groups of 1,2-diacyl-<i>sn</i>-glycero-3-phosphocholine via methanolysis and washing fatty acid byproducts with CHCl<sub>3</sub>, the obtained <i>sn</i>-glycero-3-phosphocholine (GPC) with the free diol moiety is derivatized by the chiral boronic acid and analyzed by <sup>1</sup>H NMR analysis. The choline methyl resonance of each diastereomer is observed at distinctive chemical shifts in the <sup>1</sup>H NMR spectrum. Integration of the respective resonances allows direct determination of the enantiomeric purity. The procedure was tested successfully using 1,2-dipalmitoyl-<i>sn</i>-glycero-3-phosphocholine (DPPC) with different enantiomeric purities and with commercially available 1,2-dimyristoyl-<i>sn</i>-glycero-3-phosphocholine (DMPC) and 1,2-distearoyl-<i>sn</i>-glycero-3-phosphocholine (DSPC).