Binding of small guest molecules to multivalent receptors.
The complexation of phenol derivatives, aromatic carboxylic acids, and n-octylgalactopyranoside by hydrogen-bonded exo-receptors is described. The receptors are formed by self-assembly of differently functionalized calix[4]arene dimelamines with 5,5-diethyl barbiturate or butyl cyanurate. The multivalent complementary recognition site of the receptors is used very efficiently to complex multiple guests. A 1:6 binding mode was observed for phenol derivatives forming single hydrogen bonds with all six recognition sites of an ureido functionalized receptor assembly, while 1:3 complexation was observed for phenol derivatives which form two hydrogen bonds with two different ureido recognition sites of the same receptor. Aromatic carboxylic acids are complexed in a 1:6 ratio by receptors having six amino recognition sites. The complexation of n-octylgalactopyranoside by Gly-L-Ser functionalized receptors is also described, indicating that it is possible to use small peptidic fragments to complex biologically important molecules.
ten Cate
Mattijs G J
MG
Laboratory of Supramolecular Chemistry and Technology, MESA Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands.
Reinhoudt
David N
DN
Crego-Calama
Mercedes
M
D001665:Binding Sites; D006860:Hydrogen Bonding; D008024:Ligands; D046911:Macromolecular Substances / Q000737:chemistry* / Q000378:metabolism; D008954:Models, Biological; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry* / Q000378:metabolism; D011956:Receptors, Cell Surface / Q000737:chemistry* / Q000378:metabolism
D008024:Ligands; D046911:Macromolecular Substances; D009596:Nitrophenols; D011956:Receptors, Cell Surface