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Keywords = chiral derivatizing agent (CDA)

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8 pages, 957 KiB  
Article
An Effective Method for the Evaluation of the Enantiomeric Purity of 1,2-Diacyl-sn-glycero-3-phosphocholine-Based Lipids by NMR Analysis
by Antonia Di Mola, Lorenzo de Ferra, Mauro Anibaldi, Guglielmo Monaco and Antonio Massa
Symmetry 2024, 16(5), 624; https://doi.org/10.3390/sym16050624 - 17 May 2024
Cited by 1 | Viewed by 1453
Abstract
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 [...] Read more.
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). Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Medicinal Chemistry)
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11 pages, 2921 KiB  
Article
An Explanation about the Use of (S)-Citronellal as a Chiral Derivatizing Agent (CDA) in 1H and 13C NMR for Sec-Butylamine, Methylbenzylamine, and Amphetamine: A Theoretical-Experimental Study
by Viviani Nardini, Vinicius Palaretti, Luis Gustavo Dias and Gil Valdo José da Silva
Molecules 2019, 24(15), 2830; https://doi.org/10.3390/molecules24152830 - 3 Aug 2019
Cited by 4 | Viewed by 4415
Abstract
A chiral derivatizing agent (CDA) with the aldehyde function has been widely used in discriminating chiral amines because of the easy formation of imines under mild conditions. There is a preference for the use of cyclic aldehydes as a CDA since their lower [...] Read more.
A chiral derivatizing agent (CDA) with the aldehyde function has been widely used in discriminating chiral amines because of the easy formation of imines under mild conditions. There is a preference for the use of cyclic aldehydes as a CDA since their lower conformational flexibility favors the differentiation of the diastereoisomeric derivatives. In this study, the imines obtained from the reaction between (S)-citronellal and the chiral amines (sec-butylamine, methylbenzylamine, and amphetamine) were analyzed by the nuclear Overhauser effect (NOE). Through NOE, it was possible to observe that the ends of the molecules were close, suggesting a quasi-folded conformation. This conformation was confirmed by theoretical calculations that indicated the London forces and the molecular orbitals as main justifications for this conformation. This conformational locking explains the good separation of 13C NMR signals between the diastereomeric imines obtained and, consequently, a good determination of the enantiomeric excess using the open chain (S)-citronellal as a CDA. Full article
(This article belongs to the Section Molecular Structure)
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