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

Autor: Antonia Di Mola, Lorenzo de Ferra, Mauro Anibaldi, Guglielmo Monaco, Antonio Massa
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Symmetry, Vol 16, Iss 5, p 624 (2024)
Druh dokumentu: article
ISSN: 2073-8994
DOI: 10.3390/sym16050624
Popis: In this article, we report a very efficient method for the determination of the enantiopurity of 1,2-diacyl-sn-glycero-3-phosphocholine by 1H NMR analysis using a readily available chiral derivatizing boronic acid (CDA), (R)-(2-(((1-phenylethyl)amino)methyl)phenyl)boronic acid. After the removal of the acyl groups of 1,2-diacyl-sn-glycero-3-phosphocholine via methanolysis and washing fatty acid byproducts with CHCl3, the obtained sn-glycero-3-phosphocholine (GPC) with the free diol moiety is derivatized by the chiral boronic acid and analyzed by 1H NMR analysis. The choline methyl resonance of each diastereomer is observed at distinctive chemical shifts in the 1H NMR spectrum. Integration of the respective resonances allows direct determination of the enantiomeric purity. The procedure was tested successfully using 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) with different enantiomeric purities and with commercially available 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC).
Databáze: Directory of Open Access Journals
Nepřihlášeným uživatelům se plný text nezobrazuje