Carbohydrate-based receptors with multiple thiourea binding sites. Multipoint hydrogen bond recognition of dicarboxylates and monosaccharides.
The binding properties of multitopic sugar thiourea receptors toward dicarboxylate and monosaccharide guests have been examined taking glutarate and octyl beta-D-glucopyranoside as model ligands. For the anionic hydrogen bond acceptor, both the complex stoichiometry and the association constants (K(as)) were found to be strongly dependent on the relative disposition of recognition elements in the host. In contrast, for the glucoside guest a 1:1 stoichiometry was observed in all cases, the K(as) values being largely independent of the unbound state provided that geometrically equivalent supramolecular topologies can be achieved.
Benito
J M
JM
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Aptdo. 553, E-41071 Sevilla, Spain.
Gómez-García
M
M
Jiménez Blanco
J L
JL
Ortiz Mellet
C
C
García Fernández
J M
JM
D001665:Binding Sites; D050260:Carbohydrate Metabolism; D003998:Dicarboxylic Acids / Q000378:metabolism*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000378:metabolism*; D011956:Receptors, Cell Surface / Q000737:chemistry / Q000378:metabolism*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013890:Thiourea / Q000378:metabolism*
D003998:Dicarboxylic Acids; D009005:Monosaccharides; D011956:Receptors, Cell Surface; D013890:Thiourea