Collect. Czech. Chem. Commun.
2000, 65, 667-672
https://doi.org/10.1135/cccc20000667
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
Abstract
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.
