title: Synthesis of the first water-soluble hemicryptophane host: selective recognition of choline in aqueous medium.
abstract: The first water-soluble hemicryptophane cage compound, 4, was synthesized in seven steps from commercially available products, and its complexation properties were studied. NMR and ITC experiments indicate that 4 is an efficient receptor for choline in water (ΔG° = -5.2 kcal mol(-1)). High substrate selectivity was achieved since no complexation was observed for its closely related substrates: glycine betaine and betaine aldehyde. Density functional theory calculations were performed to analyze the interactions that are involved in the formation of the inclusion complex.
authors.affiliation: Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL, 46, Allée d'Italie, F-69364 Lyon, France.
authors.forename: Aline
authors.initials: A
authors.lastname: Schmitt
authors.forename: Vincent
authors.initials: V
authors.lastname: Robert
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Dutasta
authors.forename: Alexandre
authors.initials: A
authors.lastname: Martinez
mesh_terms: D001622:Betaine / Q000031:analogs & derivatives / Q000737:chemistry; D002794:Choline / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D014867:Water
chemical_list: D011083:Polycyclic Compounds; C523242:cryptophane; D014867:Water; D001622:Betaine; C026820:betaine aldehyde; D002794:Choline