Exploring the Chiral Recognition of Carboxylates by C 2‑Symmetric Receptors Bearing Glucosamine Pendant Arms

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-09, Vol.81 (17), p.7342-7348
Main Authors: Lichosyt, Dawid, Wasiłek, Sylwia, Jurczak, Janusz
Format: Article
Language:English
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Summary: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 K S /K R 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00763