Influence of the size and geometry of the anion binding pocket of sugar–urea anion receptors on chiral recognition

Influence of the size and geometry of the anion binding pocket of sugar–urea anion receptors on chiral recognition

Three new chiral urea-type anion receptors were synthesized from aromatic diamines and 1-amino-1-deoxyglucose. The anion binding properties of these receptors were studied using chiral carboxylates derived from mandelic acid and three α-amino acids. We found that the size of the anion binding pocket...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 54; no. 41; pp. 5608 - 5611
Main Authors: Hamankiewicz, Paulina, Granda, Jarosław M., Jurczak, Janusz
Format: Journal Article
Language:English
Published: Elsevier Ltd 09-10-2013
Subjects:
Anion binding
Chiral recognition
Monosaccharides
Urea
Urea
Anion binding
Chiral recognition
Monosaccharides
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Summary:Three new chiral urea-type anion receptors were synthesized from aromatic diamines and 1-amino-1-deoxyglucose. The anion binding properties of these receptors were studied using chiral carboxylates derived from mandelic acid and three α-amino acids. We found that the size of the anion binding pocket played an important role in chiral recognition processes. The best results were obtained for 1,8-diaminoanthracene and α-amino acid anions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.08.019