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Kozbia, Małgorzat; Pietraszkiewicz, Marek; Pietraszkiewicz, Oksana

doi:10.1023/a:1007944024868

Cited by 11 publications

(1 citation statement)

References 4 publications

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“…In these chiral stationary phases, chiral crown ethers are mainly covalently bonded to polystyrene or silica gel. Also, some supported liquid membrane applications of crown ethers have been reported in literature [16][17][18][19][20][21][22][23][24][25][26][27][28][29]. Although this technique can be considered similar to EIR its major drawback is that the selectivity is strongly depending on the permeation rate of the complexes inside the membrane, not on the distribution ratio.…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of amino-alcohols using extractant impregnated resins

Babić

Driessen

Ham

et al. 2007

Journal of Chromatography A

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Section: Introductionmentioning

confidence: 99%

Chiral separation of amino-alcohols using extractant impregnated resins

Babić

Driessen

Ham

et al. 2007

Journal of Chromatography A

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Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid

2011

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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.

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Experimental evidence of chiral crown ether complexation with aromatic amino acids

Koźbiał

Poznański

2007

J of Physical Organic Chem

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The complexation of L‐ and D‐enantiomers of phenylglycine, phenylalanine, and tryptophan with D‐mannonaphto‐crown‐6‐ether in methanol solution was studied by NMR and isothermal titration calorimetry (ITC) at 298.15 K. The total heat effects attributed to the binding phenomena were measured in the range of 1.8 to 7.7 mJ, and the complexation was found stereo‐specific. The binding topologies were estimated basing on 1H 2D‐ROESY experiments. The analysis of Job plots obtained from 1H NMR‐monitored titrations proved the coexistence of 1:1 and 1:2 (crown ether:amino acids) complexes, which thermodynamic parameters, Ks, ΔG, ΔH°, and TΔS were determined with the aid of ITC. The 1:1 complexes were found enthalpically stabilized, generally by electrostatic interactions between the charged NH 3+ group of amino acid and crown ether macrocyclic moiety, while the binding of the second amino acid molecule was driven entropically due to solvatophobic effect. Strong enthalpy–entropy compensation points towards the uniform binding mode of all complexes studied. The mode of complex formation was found solvent dependent. For phenylalanine guest studied in various solvent systems, in contrast to the aqueous media, the noticeable chiral recognition is observed in methanol solution, and the complex stoichiometry (1:2 ether:Phe) differs from the 2:1 one, determined previously for the same host‐guest system in water (J. Thermal. Anal. Cal. 2006; 83: 575–578). Copyright © 2007 John Wiley & Sons, Ltd.

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Untitled

Cited by 11 publications

References 4 publications

Chiral separation of amino-alcohols using extractant impregnated resins

Chiral separation of amino-alcohols using extractant impregnated resins

Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid

Experimental evidence of chiral crown ether complexation with aromatic amino acids

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