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A Highly Enantioselective Receptor for N-Protected Glutamate and Anomalous Solvent-Dependent Binding Properties
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2002
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Synaptic TransmissionStrong BindingNeurotransmitterNeurotransmissionSynaptic SignalingCompetitive Solvent Cdcl3Highly Enantioselective ReceptorN-protected GlutamateBiochemistryG Protein-coupled ReceptorReceptor (Biochemistry)Mechanism Of ActionNeuropharmacologyPharmacologyFunctional SelectivityPolar SolventsMolecular SubstrateMedicineDrug Discovery
Solvation of the macrocycle by polar solvents leads to strong binding of an N-protected excitatory amino acid neurotransmitter. A 1:1 complex forms highly enantioselectively between the macrocycle and N-Boc-L-glutamate (as the dicarboxylate anion, see picture) in CH3CN and DMSO (with a larger entropic driving force for binding), but no binding occurs in the less competitive solvent CDCl3. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2002/z19311_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.