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Exploration of the Chiral Recognition of Sugar‐Based Diindolylmethane Receptors: Anion and Receptor Structures
Author(s) -
Granda Jarosław M.,
Jurczak Janusz
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502932
Subject(s) - substituent , receptor , chemistry , stereochemistry , carboxylic acid , anomer , hydrogen bond , molecular recognition , combinatorial chemistry , biochemistry , molecule , organic chemistry
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.