Recognition properties of an acyclic biphenyl-based receptor toward carbohydrates.
Biphenyl-based receptor 1, incorporating four heterocyclic recognition units, was synthesized, and its binding properties toward neutral sugars were determined. Receptor 1 is a representative of a new series of acyclic carbohydrate-binding receptors, which were designed to recognize disaccharides. The compound 1 has been established as a highly effective receptor for dodecyl beta-D-maltoside, showing successive 1:1 and 2:1 receptor/substrate complexation behavior toward the disaccharide. Both hydrogen bonding and interactions of the sugar CH's with the aromatic units of the receptor contribute to the stabilization of the receptor-maltoside complexes.
Mazik
Monika
M
Institut für Organische Chemie der Technischen Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany. m.mazik@tu-bs.de
König
Alexander
A
D001665:Binding Sites; D001713:Biphenyl Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry; D006860:Hydrogen Bonding
D001713:Biphenyl Compounds; D002241:Carbohydrates; D004187:Disaccharides