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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.


1H HR-MAS NMR of (A) (R)-enantiomer (13.0 mmol.L-1), (B) (S)-enantiomer (13.0 mmol.L-1), and (C) racemic mixture (13.0 mmol.L-1) in the presence of 1 mg of CSP suspended in ACNd3/DEA (100:0.1, v/v).
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pone.0162892.g004: 1H HR-MAS NMR of (A) (R)-enantiomer (13.0 mmol.L-1), (B) (S)-enantiomer (13.0 mmol.L-1), and (C) racemic mixture (13.0 mmol.L-1) in the presence of 1 mg of CSP suspended in ACNd3/DEA (100:0.1, v/v).

Mentions: The NMR spectra obtained for the (R)-enantiomer (A) and (S)-enantiomer (B) and the racemic mixture (C) in the presence of CSP-ID are illustrated in Fig 4.


A High-Resolution Magic Angle Spinning NMR Study of the Enantiodiscrimination of 3,4-Methylenedioxymethamphetamine (MDMA) by an Immobilized Polysaccharide-Based Chiral Phase
1H HR-MAS NMR of (A) (R)-enantiomer (13.0 mmol.L-1), (B) (S)-enantiomer (13.0 mmol.L-1), and (C) racemic mixture (13.0 mmol.L-1) in the presence of 1 mg of CSP suspended in ACNd3/DEA (100:0.1, v/v).
© Copyright Policy
Related In: Results  -  Collection

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

pone.0162892.g004: 1H HR-MAS NMR of (A) (R)-enantiomer (13.0 mmol.L-1), (B) (S)-enantiomer (13.0 mmol.L-1), and (C) racemic mixture (13.0 mmol.L-1) in the presence of 1 mg of CSP suspended in ACNd3/DEA (100:0.1, v/v).
Mentions: The NMR spectra obtained for the (R)-enantiomer (A) and (S)-enantiomer (B) and the racemic mixture (C) in the presence of CSP-ID are illustrated in Fig 4.

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.