Enantio- and Substrate-Selective Recognition of Chiral Neurotransmitters with <i>C</i><sub>3</sub>-Symmetric Switchable Receptors
Jian Yang, Bastien Châtelet, Véronique Dufaud, Damien Hérault, Marion Jean, Nicolas Vanthuyne, Jean‐Christophe Mulatier, Delphine Pitrat, Laure Guy, Jean‐Pierre Dutasta, Alexandre Martinez
Abstract
We report on the synthesis of C3-symmetric enantiopure cage molecules 1, which exhibit remarkable to exclusive enantioselective recognition properties toward chiral ammonium neurotransmitters. Strong changes in the substrate selectivity are also observed when different stereoisomers of 1 are used. Furthermore, protonation/deprotonation induces a reversible modification of the conformation of 1, which switches from an imploded to an inflated form, leading to ejection and reuptake of the guest initially encaged inside the cavity.
Topics & Concepts
Enantiopure drugChemistryProtonationEnantioselective synthesisSubstrate (aquarium)DeprotonationSelectivityStereochemistryMoleculeMolecular recognitionCombinatorial chemistryOrganic chemistryCatalysisGeologyIonOceanographyMolecular Sensors and Ion DetectionSupramolecular Chemistry and ComplexesNeuroscience and Neuropharmacology Research