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• W2025431928 endingPage "3231" @default.
• W2025431928 startingPage "3223" @default.
• W2025431928 abstract "Bisurea calix[4]arenes 1 and 2 possessing L-amino acid moieties at the lower rim were synthesized by reaction of the methyl esters of glycine, L-alanine, or L-isoleucine with the appropriate isocyanate (12 or 13), obtained with a safe and efficient Curtius rearrangement from the corresponding carboxylic acid derivatives. The conformational properties of the ligands 1 and 2 were investigated by means of a combined NMR and molecular modeling study which evidences that they are deeply influenced by strong intramolecular H-bonds between the urea NH groups and the vicinal phenolic oxygen atoms or the opposite urea C=O group. Complexation studies performed by ESI-MS and NMR spectroscopy in acetone solution show that the binding ability of these bisurea hosts decreases by increasing the side chain size of the amino acid. Host 2b has a remarkable binding ability for the N-acetyl-D-phenylalaninate anion with an interesting enantioselectivity (KDass/KLass=4.14), which is explained on the basis of a three-point interaction mode of binding." @default.
• W2025431928 created "2016-06-24" @default.
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• W2025431928 date "2007-03-27" @default.
• W2025431928 modified "2023-10-08" @default.
• W2025431928 title "<i>N-</i>Linked Peptidocalix[4]arene Bisureas as Enantioselective Receptors for Amino Acid Derivatives" @default.
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• W2025431928 doi "https://doi.org/10.1021/jo062410x" @default.
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