title: Molecular recognition of carbohydrates with acyclic pyridine-based receptors.
abstract: The recognition capabilities of acyclic pyridine-based receptors toward monosaccharides were evaluated. Aminopyridine receptors based on the 2,4,6-trimethyl- or 2,4,6-triethylbenzene frame show high beta vs alpha binding selectivity in the recognition of glucopyranosides. Amidopyridine receptors, which are sterically less hindered at nitrogen, display high efficiency and an inverse selectivity. The 2-aminopyridine group has been established as a highly effective recognition group in the binding of monosaccharides. The factors influencing the binding properties of receptors 1-15, which differ in the nature and number of binding and spacer subunits used as the buildings blocks, are discussed.
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: Wolfgang
authors.initials: W
authors.lastname: Radunz
authors.forename: Roland
authors.initials: R
authors.lastname: Boese
mesh_terms: D001665:Binding Sites; D002241:Carbohydrates / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011956:Receptors, Cell Surface / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D002241:Carbohydrates; D011725:Pyridines; D011956:Receptors, Cell Surface; C027786:glucose receptor; C023666:pyridine