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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 STD HR-MAS NMR for: (A) (R)-MDMA (13.0 mmol.L-1), on resonance, (B) (S)-MDMA (13.0 mmol.L-1) ON-resonance and (C) MDMA racemic mixture (13.0 mmol.L-1) OFF-resonance.
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pone.0162892.g006: 1H STD HR-MAS NMR for: (A) (R)-MDMA (13.0 mmol.L-1), on resonance, (B) (S)-MDMA (13.0 mmol.L-1) ON-resonance and (C) MDMA racemic mixture (13.0 mmol.L-1) OFF-resonance.

Mentions: The comparison of the spectra of Fig 6A and 6B with the spectra at of Fig 6C reveals that the later has a new set of proton signals corresponding to H2 (-CH3), H5-H6 (aromatic), and H8 (-CH2). In the spectrum of (S)-MDMA-CSP-ID (Fig 6B), the aromatic proton signals are of lower intensity when compared to those of (R)- MDMA-CSP-ID (Fig 6A).


A High-Resolution Magic Angle Spinning NMR Study of the Enantiodiscrimination of 3,4-Methylenedioxymethamphetamine (MDMA) by an Immobilized Polysaccharide-Based Chiral Phase
1H STD HR-MAS NMR for: (A) (R)-MDMA (13.0 mmol.L-1), on resonance, (B) (S)-MDMA (13.0 mmol.L-1) ON-resonance and (C) MDMA racemic mixture (13.0 mmol.L-1) OFF-resonance.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0162892.g006: 1H STD HR-MAS NMR for: (A) (R)-MDMA (13.0 mmol.L-1), on resonance, (B) (S)-MDMA (13.0 mmol.L-1) ON-resonance and (C) MDMA racemic mixture (13.0 mmol.L-1) OFF-resonance.
Mentions: The comparison of the spectra of Fig 6A and 6B with the spectra at of Fig 6C reveals that the later has a new set of proton signals corresponding to H2 (-CH3), H5-H6 (aromatic), and H8 (-CH2). In the spectrum of (S)-MDMA-CSP-ID (Fig 6B), the aromatic proton signals are of lower intensity when compared to those of (R)- MDMA-CSP-ID (Fig 6A).

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.