Collect. Czech. Chem. Commun. 2000, 65, 667-672

A Stereoselective Peptide-Based Artificial Receptor for Sugar Derivatives

Frank Eblinger and Hans-Jörg Schneider*

FR Organische Chemie , Universität des Saarlandes, D 66041 Saarbrücken, Germany


A lipophilic sugar receptor containing two phenylalanine moieties shows in chloroform complexation free energies of ∆G = 13 kJ/mol for an alkyl glucoside, discriminating the corresponding galactoside by at least 8 kJ/mol. The observed 1H NMR signal shifts at OH groups suggest the hydrogen bonds as the major driving force, in line with preliminary molecular mechanics simulations.

Keywords: Carbohydrate receptors; Glycosides; Amides; Supramolecular complexes; Hydrogen bonds; Peptide-sugar interactions.

References: 32 live references.