calixarenes and mandelic-acid

Herein, we reported a new strategy based on self-assembly chemistry for chiral discrimination of glucose on a new S-mandelic acid-appended calix[4]arene (S-MC4) modified nanostructure, which exhibits macroscopic chiral preference for d-glucose via contact angle measurements (CA). The proposed macroscopic chiral device displays rapidly remarkable specificity and is convenient to use, which should be suitable for diagnostic purposes, nanomedical applications, etc.

Topics: Calixarenes; Glucose; Mandelic Acids; Models, Molecular; Stereoisomerism; Surface Properties; Wettability

Novel chiral calix[4]arene derivatives bearing amino alcohol moieties at the lower rim have been synthesized from the reaction of p-tert-butylcalix[4]arene diester with various amino alcohols. The transport of amino acid esters (phenylglycine, phenylalanine, and tryptophan methyl esters hydrochloride) and mandelic acid were studied through chloroform bulk liquid membrane system using chiral calix[4]arenes 15-20. All these receptors have been found to act as carriers for transport of aromatic amino acid methylesters and mandelic acid from the aqueous source phase to the aqueous receiving phase. The influence of calixarene and guest structures upon transport through liquid membrane is discussed.

Topics: Amino Alcohols; Calixarenes; Drug Carriers; Hydrogen-Ion Concentration; Mandelic Acids; Membranes; Methyl Ethers; Spectrophotometry, Ultraviolet; Stereoisomerism

A chiral 1,1-bi-2-naphthol-derived calix[4]arene (1) was synthesized via a click reaction. Fluorescence spectra and dynamic light-scattering revealed that Cu(II)-1 complexes were generated in situ and exhibited remarkable enantioselectivity toward mandelic acid. Using this dynamic light-scattering technique, the detection sensitivity was improved almost 100-fold, with a detection limit of 2.0 × 10(-7) M, compared with fluorescent methods.

Topics: Calixarenes; Click Chemistry; Fluorescence; Magnetic Resonance Spectroscopy; Mandelic Acids; Molecular Structure; Naphthols; Phenols

A newly designed inherently chiral calix[4]arene was synthesized and resolved to an optically pure form. Enantiomeric recognition ability of the chiral calix[4]arene was examined using 1H NMR experiments with mandelic acid. In addition, the chiral calix[4]arene was applied to asymmetric reactions, as an organocatalyst.

Topics: Calixarenes; Catalysis; Magnetic Resonance Spectroscopy; Mandelic Acids; Molecular Structure; Phenols; Stereoisomerism

Calixarenes bearing optically pure alpha,beta-amino alcohol groups at their lower rim exhibit exceptional and efficient chiral recognition ability in discrimination of racemic mandelic acid, 2,3-dibenzoyltartaric acid and 2-hydroxy-3-methylbutyric acid. [structure: see text]

Topics: Amino Alcohols; Calixarenes; Carboxylic Acids; Hemiterpenes; Mandelic Acids; Molecular Structure; Pentanoic Acids; Phenols; Stereoisomerism; Tartrates