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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.


Elution order of MDMA enantiomers in ACNd3/DEA (100:0.1, v/v).Flow rate of 5.0 mL.min-1, λ = 270 nm and injection volume of 0.5 mL.min-1.
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pone.0162892.g002: Elution order of MDMA enantiomers in ACNd3/DEA (100:0.1, v/v).Flow rate of 5.0 mL.min-1, λ = 270 nm and injection volume of 0.5 mL.min-1.

Mentions: For 1H HR-MAS NMR experiments, first it is necessary to obtain the enantiomers in a high degree of enantiomeric purity. The MDMA enantiomers (135 mg) were separated by a total of 27 continuous injections (2.64 h), providing a throughput of almost 577 mg.d-1 for the enantiomers. The first (S)-enantiomer (63.1 mg) and the second (R)-enantiomer (64.0 mg) were both obtained in recoveries higher than 93%. Enantiomeric purity higher than 99.9% was obtained for both enantiomers (Fig 2).


A High-Resolution Magic Angle Spinning NMR Study of the Enantiodiscrimination of 3,4-Methylenedioxymethamphetamine (MDMA) by an Immobilized Polysaccharide-Based Chiral Phase
Elution order of MDMA enantiomers in ACNd3/DEA (100:0.1, v/v).Flow rate of 5.0 mL.min-1, λ = 270 nm and injection volume of 0.5 mL.min-1.
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Related In: Results  -  Collection

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getmorefigures.php?uid=PMC5036802&req=5

pone.0162892.g002: Elution order of MDMA enantiomers in ACNd3/DEA (100:0.1, v/v).Flow rate of 5.0 mL.min-1, λ = 270 nm and injection volume of 0.5 mL.min-1.
Mentions: For 1H HR-MAS NMR experiments, first it is necessary to obtain the enantiomers in a high degree of enantiomeric purity. The MDMA enantiomers (135 mg) were separated by a total of 27 continuous injections (2.64 h), providing a throughput of almost 577 mg.d-1 for the enantiomers. The first (S)-enantiomer (63.1 mg) and the second (R)-enantiomer (64.0 mg) were both obtained in recoveries higher than 93%. Enantiomeric purity higher than 99.9% was obtained for both enantiomers (Fig 2).

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.