title: Exploration of the Chiral Recognition of Sugar-Based Diindolylmethane Receptors: Anion and Receptor Structures.
abstract: In this study, we have conducted a systematic investigation of the chiral recognition of carboxylic anions by D-glucuronic acid/diindolylmethane receptors. We investigate the influence of the anion structure on chiral recognition in the diindolylmethane/glucuronic acid-based receptor 1 a. We found that presence of an additional hydrogen-bond donor at the α position to the carboxylic function is essential for effective chiral differentiation in these systems. Furthermore, we present a synthetic procedure that allows for the synthesis of sugar-decorated receptors that possess a modified substituent at the anomeric position. Four new receptors 1 b-e have been synthesized, and their chiral-discrimination ability toward model carboxylates is studied. The obtained results show that the chiral recognition of these receptors can be fine-tuned by incorporation of a proper substituent into the receptor structure.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland).
authors.forename: Jarosław M
authors.initials: JM
authors.lastname: Granda
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland). janusz.jurczak@icho.edu.pl.
authors.forename: Janusz
authors.initials: J
authors.lastname: Jurczak
keywords: anions; carbohydrates; chirality; receptors; supramolecular chemistry