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A High-Resolution Magic Angle Spinning NMR Study of the Enantiodiscrimination of 3,4-Methylenedioxymethamphetamine (MDMA) by an Immobilized Polysaccharide-Based Chiral Phase

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ABSTRACT

This paper reports the investigation of the chiral interaction between 3,4-methylenedioxy-methamphetamine (MDMA) enantiomers and an immobilized polysaccharide-based chiral phase. For that, suspended-state high-resolution magic angle spinning nuclear magnetic resonance spectroscopy (1H HR-MAS NMR) was used. 1H HR-MAS longitudinal relaxation time and Saturation Transfer Difference (STD NMR) titration experiments were carried out yielding information at the molecular level of the transient diastereoisomeric complexes of MDMA enantiomers and the chiral stationary phase. The interaction of the enantiomers takes place through the aromatic moiety of MDMA and the aromatic group of the chiral selector by π-π stacking for both enantiomers; however, a stronger interaction was observed for the (R)-enantiomer, which is the second one to elute at the chromatographic conditions.

No MeSH data available.


The structures of MDMA enantiomers with the percentage of signals intensity as obtained from the STD experiments.The first structure corresponds to the (S)-MDMA and the second to (R)-MDMA.
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pone.0162892.g007: The structures of MDMA enantiomers with the percentage of signals intensity as obtained from the STD experiments.The first structure corresponds to the (S)-MDMA and the second to (R)-MDMA.

Mentions: The STD signals were normalized with respect to the registered signal of highest intensity (ACNd3 –solvent signal), which was assigned as 100%. The percentage signal intensities are given in Fig 7.


A High-Resolution Magic Angle Spinning NMR Study of the Enantiodiscrimination of 3,4-Methylenedioxymethamphetamine (MDMA) by an Immobilized Polysaccharide-Based Chiral Phase
The structures of MDMA enantiomers with the percentage of signals intensity as obtained from the STD experiments.The first structure corresponds to the (S)-MDMA and the second to (R)-MDMA.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5036802&req=5

pone.0162892.g007: The structures of MDMA enantiomers with the percentage of signals intensity as obtained from the STD experiments.The first structure corresponds to the (S)-MDMA and the second to (R)-MDMA.
Mentions: The STD signals were normalized with respect to the registered signal of highest intensity (ACNd3 –solvent signal), which was assigned as 100%. The percentage signal intensities are given in Fig 7.

View Article: PubMed Central - PubMed

ABSTRACT

This paper reports the investigation of the chiral interaction between 3,4-methylenedioxy-methamphetamine (MDMA) enantiomers and an immobilized polysaccharide-based chiral phase. For that, suspended-state high-resolution magic angle spinning nuclear magnetic resonance spectroscopy (1H HR-MAS NMR) was used. 1H HR-MAS longitudinal relaxation time and Saturation Transfer Difference (STD NMR) titration experiments were carried out yielding information at the molecular level of the transient diastereoisomeric complexes of MDMA enantiomers and the chiral stationary phase. The interaction of the enantiomers takes place through the aromatic moiety of MDMA and the aromatic group of the chiral selector by π-π stacking for both enantiomers; however, a stronger interaction was observed for the (R)-enantiomer, which is the second one to elute at the chromatographic conditions.

No MeSH data available.