Chiral Discrimination of Ammonium Neurotransmitters by C3-Symmetric Enantiopure Hemicryptophane Hosts

ABSTRACT Enantiopure hemicryptophanes efficiently discriminate chiral ammonium neurotransmitters. The ephedrine and norephedrine molecules associate with hemicryptophane hosts to form 1:1 and 1:2 host‐guest complexes. Binding constants are determined by fitting the 1H nuclear magnetic resonance (NMR...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2013-08, Vol.25 (8), p.475-479
Main Authors: Schmitt, Aline, Chatelet, Bastien, Collin, Solène, Dutasta, Jean-Pierre, Martinez, Alexandre
Format: Article
Language:English
Subjects:
Ammonium Compounds - chemistry
Chemical Sciences
chiral recognition
enantioselective discrimination
Ephedrine - analysis
Ephedrine - chemistry
hemicryptophane
host-guest complexes
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
neurotransmitter
Neurotransmitter Agents - chemistry
or physical chemistry
Polycyclic Compounds - chemistry
Stereoisomerism
supramolecular chemistry
Theoretical and
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Summary:ABSTRACT Enantiopure hemicryptophanes efficiently discriminate chiral ammonium neurotransmitters. The ephedrine and norephedrine molecules associate with hemicryptophane hosts to form 1:1 and 1:2 host‐guest complexes. Binding constants are determined by fitting the 1H nuclear magnetic resonance (NMR) titration curves to give β1 and β2 values, which are used to characterize the diastereomeric and enantiomeric discriminating potentials of the hosts. Chirality 25:47–479, 2013. © 2013 Wiley Periodicals, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22195