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

Author(s)

Barreiro, Juliana C. ; Paixao, Marcio W. ; Lourenco, Tiago C. ; Cass, Quezia B. ; Venancio, Tiago

• Document type: Journal article
• Source: PLoS One; v. 11, n. 9 SEP 26 2016.
• Web of Science Citations: 2

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 (H-1 HR-MAS NMR) was used. (HHR)-H-1-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 pi-pi 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. (AU)

• FAPESP's process: 08/05778-1 - Chiral pharmaceuticals in wastewaters: quantification and studies of enantioselective separation mechanisms
• Grantee: Juliana Cristina Barreiro
• Support Opportunities: Scholarships in Brazil - Post-Doctoral