Molecular recognition of carbohydrates with acyclic pyridine-based receptors.
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.
Mazik
Monika
M
Institut für Organische Chemie der Technischen Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany. m.mazik@tu-bs.de
Radunz
Wolfgang
W
Boese
Roland
R
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
D002241:Carbohydrates; D011725:Pyridines; D011956:Receptors, Cell Surface; C027786:glucose receptor; C023666:pyridine