Exploration of the Chiral Recognition of Sugar‐Based Diindolylmethane Receptors: Anion and Receptor Structures. Issue 46 (29th September 2015)

• Record Type: Journal Article
• Authors: Granda, Jarosław M.; Jurczak, Janusz
• Is Part Of: Chemistry. Volume 21:Issue 46(2015)
• Page Start: 16585
• Page End: 16592
• Publication Date: 2015-09-29
• Subjects: anions -- carbohydrates -- chirality -- receptors -- supramolecular chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201502932
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : The anomeric substituent does ­ matter : Chiral recognition by sugar‐decorated diindolylmethane‐based receptors can be tailored by modification of the substituent present at the anomeric position. The chiral‐discrimination ability of receptors 1 a –e toward model carboxylates was studied (see picture).