PMID- 27668862
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20191120
IS  - 1932-6203 (Electronic)
IS  - 1932-6203 (Linking)
VI  - 11
IP  - 9
DP  - 2016
TI  - A High-Resolution Magic Angle Spinning NMR Study of the Enantiodiscrimination of 
      3,4-Methylenedioxymethamphetamine (MDMA) by an Immobilized Polysaccharide-Based 
      Chiral Phase.
PG  - e0162892
LID - 10.1371/journal.pone.0162892 [doi]
LID - e0162892
AB  - 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 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.
FAU - Barreiro, Juliana C
AU  - Barreiro JC
AD  - Department of Chemistry, Federal University of Sao Carlos, Sao Paulo, Brazil.
FAU - Paixao, Marcio W
AU  - Paixao MW
AD  - Department of Chemistry, Federal University of Sao Carlos, Sao Paulo, Brazil.
FAU - Lourenco, Tiago C
AU  - Lourenco TC
AD  - Scientific Director of Apex Science, Campinas, Sao Paulo, Brazil.
FAU - Cass, Quezia B
AU  - Cass QB
AD  - Department of Chemistry, Federal University of Sao Carlos, Sao Paulo, Brazil.
FAU - Venancio, Tiago
AU  - Venancio T
AD  - Department of Chemistry, Federal University of Sao Carlos, Sao Paulo, Brazil.
LA  - eng
PT  - Journal Article
DEP - 20160926
PL  - United States
TA  - PLoS One
JT  - PloS one
JID - 101285081
PMC - PMC5036802
COIS- Competing Interests: Co-author Tiago C. Lourenco is employed by Apex Science, a 
      commercial company. There are no patents, products in development or marketed 
      products to declare. This does not alter our adherence to all the PLOS ONE 
      policies on sharing data and materials.
EDAT- 2016/09/27 06:00
MHDA- 2016/09/27 06:01
PMCR- 2016/09/26
CRDT- 2016/09/27 06:00
PHST- 2015/12/30 00:00 [received]
PHST- 2016/08/30 00:00 [accepted]
PHST- 2016/09/27 06:00 [entrez]
PHST- 2016/09/27 06:00 [pubmed]
PHST- 2016/09/27 06:01 [medline]
PHST- 2016/09/26 00:00 [pmc-release]
AID - PONE-D-15-56404 [pii]
AID - 10.1371/journal.pone.0162892 [doi]
PST - epublish
SO  - PLoS One. 2016 Sep 26;11(9):e0162892. doi: 10.1371/journal.pone.0162892. 
      eCollection 2016.