Granda Jarosław M, Jurczak Janusz
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland).
Chemistry. 2015 Nov 9;21(46):16585-92. doi: 10.1002/chem.201502932. Epub 2015 Sep 29.
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.
在本研究中，我们对D-葡萄糖醛酸/二吲哚甲烷受体对羧酸根阴离子的手性识别进行了系统研究。我们研究了阴离子结构对基于二吲哚甲烷/葡萄糖醛酸的受体1 a中手性识别的影响。我们发现，在羧酸官能团的α位存在额外的氢键供体对于这些体系中的有效手性区分至关重要。此外，我们提出了一种合成方法，该方法允许合成在异头位置具有修饰取代基的糖修饰受体。已经合成了四种新的受体1 b - e，并研究了它们对模型羧酸盐的手性识别能力。所得结果表明，通过将适当的取代基引入受体结构中，可以对这些受体的手性识别进行微调。
