Enantio- and Substrate-Selective Recognition of Chiral Neurotransmitters with C3-Symmetric Switchable Receptors

• DOI: 10.1021/acs.orglett.9b04440
• Publication Date: 2020-01-27T15:28:36Z
• Authors: Jian Yang; Bastien Chatelet; Véronique Dufaud; Damien Hérault; Marion Jean; Nicolas Vanthuyne; Jean-Christophe M...; Delphine Pitrat; Laure Guy; Jean-Pierre Dutasta; Alexandre Martinez
• Keywords: Enantiopure drug; Molecular Recognition

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 substrate selectivity are also observed when different stereoisomers 1 used. Furthermore, protonation/deprotonation induces a reversible modification conformation switches from an imploded inflated form, leading ejection and reuptake guest initially encaged inside cavity.