title: 8-Hydroxyquinoline as a building block for artificial receptors: binding preferences in the recognition of glycopyranosides.
abstract: 8-Hydroxyquinoline-based receptors 1-3, containing a trisubstituted triethylbenzene core, were prepared and their binding properties towards glycosides were evaluated. (1)H NMR and fluorescence titrations as well as binding studies in two-phase systems, such as dissolution of solid carbohydrates in apolar media and phase transfer of sugars from aqueous into organic solvents, revealed β- vs.α-anomer binding preferences in the recognition of glycosides. Compared to the previously described three-armed aminopyridine-based receptor, compounds 1 and 2 showed significantly increased affinity to β-galactoside. Receptor 2, incorporating two 8-hydroxyquinoline units, was shown to be the most effective receptor for β-galactoside. Compound 3, bearing one 8-hydroxyquinoline group, was found to be a highly effective receptor for β-glucoside and shown to be a more powerful receptor than the quinoline-based compound 4, indicating an important role of the quinoline hydroxy group in the complex formation.
authors.affiliation: Institut für Organische Chemie der Technischen Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany. m.mazik@tu-bs.de
authors.forename: Monika
authors.initials: M
authors.lastname: Mazik
authors.forename: Christoph
authors.initials: C
authors.lastname: Geffert
mesh_terms: D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D015125:Oxyquinoline / Q000737:chemistry*; D012995:Solubility
chemical_list: D006027:Glycosides; D015125:Oxyquinoline