Exploring the Chiral Recognition of Carboxylates by C2-Symmetric Receptors Bearing Glucosamine Pendant Arms
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- 作者：Dawid Lichosyt ; Sylwia Wasiłek ; Janusz Jurczak
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：September 2, 2016
- 年：2016
- 卷：81
- 期：17
- 页码：7342-7348
- 全文大小：479K
- 年卷期：0
- ISSN：1520-6904
文摘
Two urea-based receptors containing a glucosamine derivative were synthesized and investigated in terms of their ability to recognize chiral and achiral anions. Both receptors demonstrated a high affinity toward carboxylates in very competitive DMSO/water mixtures. The chiral recognition properties of these compounds were studied using structurally differentiated guests derived from mandelic acid and α-amino acids. We found that receptor 1 exhibits significantly higher enantioselectivities than compound 2 for all anions investigated, with a KS/KR ratio of up to 2. This low enantiodiscrimination in the case of receptor 2 is attributed to a lack of interactions between its sugar moieties and the side chain of chiral anions, due to their inadequate spatial arrangement.