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Exploring the Chiral Recognition of Carboxylates by C2‑Symmetric Receptors Bearing Glucosamine Pendant Arms

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journal contribution
posted on 27.07.2016, 00:00 by Dawid Lichosyt, Sylwia Wasiłek, Janusz Jurczak
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.

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