Chiral lariat ethers as membrane carriers for chiral amino acids and their sodium and potassium salts

Aydın, Işıl; Aral, Tarık; Karakaplan, Mehmet; Hoşgören, Halil

doi:10.1016/j.tetasy.2009.01.005

Cited by 14 publications

(9 citation statements)

References 27 publications

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“…It is known that chiral recognition occurs via ion‐dipole and hydrogen bonding by inclusion complexation in chiral selectors such as crown ether and cyclodextrin . We fabricated membranes using CC as a chiral dopant in order to determine the importance of hydrogen bonding in chiral recognition interactions with the LC phases.…”

Section: Resultsmentioning

confidence: 99%

“…Because of the weaker interactions between the ChLC phase and the enantiomers, which are not as strong as the multiple hydrogen bonding interactions reported in cyclodextrin and crown ether‐based porous membranes, the SLCMs exhibited a constant enantioselectivity of ~1.2 over 14 h (S4 in supporting information). This suggests that the membranes will not suffer the same drop‐off in selectivity observed in some other porous membranes.…”

Section: Resultsmentioning

confidence: 99%

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Enantioselective separations using chiral supported liquid crystalline membranes

et al. 2012

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Porous and nonporous supported liquid crystalline membranes were produced by impregnating porous cellulose nitrate supports with cholesteric liquid crystal (LC) materials consisting of 4-cyano-4'-pentylbiphenyl (5CB) mixed with a cholesterol-based dopant (cholesteryl oleyl carbonate [COC], cholesteryl nonanoate [CN], or cholesteryl chloride [CC]). The membranes exhibit selectivity for R-phenylglycine and R-1-phenylethanol because of increased interactions between the S enantiomers and the left-handed cholesteric phase. The selectivity of both phenylglycine and 1-phenylethanol in 5CB/CN membranes decreases with effective pore diameter while the permeabilities increase, as expected. Phenylglycine, which is insoluble in the LC phase, exhibits no transport in the nonporous (completely filled) membranes; however, 1-phenylethanol, which is soluble in the LC phase, exhibits transport but negligible enantioselectivity. The enantioselectivity for 1-phenylethanol was higher (1.20 in 5CB/COC and 5CB/CN membranes) and the permeability was lower in the cholesteric phase than in the isotropic phase. Enantioselectivity was also higher in the 5CB/COC cholesteric phase than in the nematic phase of undoped 5CB (1.03). Enantioselectivity in the cholesteric phase of 5CB doped with CC (1.1), a dopant lacking hydrogen bonding groups, was lower than in the 5CB/COC phases. Finally, enantioselectivity increases with the dopant concentration up to a plateau value at approximately 17 mol%.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Enantioselective separations using chiral supported liquid crystalline membranes

et al. 2012

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“…Indeed, calixarene derivatives, the lower rims of which have been functionalized with chiral moieties, such as tartaric ester,22 aminonaphthol units,48 and others,49–52 have been used for chiral recognition 53. The rigidity of the microenvironment of the cavity and the nature of the chiral substituents were critical for enantiomeric recognition 19…”

Section: Resultsmentioning

confidence: 99%

Silica Colloidal Membranes with Enantioselective Permeability

Leon

Abelow

Cichelli

et al. 2014

Israel Journal of Chemistry

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Dedicated to the memory of Professor Michael Bendikov: a brilliant scientist, a great friend, and a courageous man ties in the range of 1.2-1.8, which were not significantly affected by the structure of the surface-immobilized chiral electors. This selectivity is on par with most reported polymer-based solid membranes and bulk liquid membranes. The enantioselectivity results from the surface-facilitated mechanism of transport of enantiomers through the mesopores.

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“…The estimated errors (<10%) are consistent with those reported in the literature. 47 A blank experiment using the organic solvent without the carrier indicated that the enantioselectivity of amino acids was negligible. The feed phase was an aqueous solution (5 ml) of amino acid methyl ester hydrochloride 2.0 3 10 24 or 7.0 3 10 23 M at pH 5 5.5 value obtained by adding HCl or LiOH.…”

Section: Liquid Membrane Transport Of Amino Acid Methyl Esters and Mamentioning

confidence: 99%

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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Chiral lariat ethers as membrane carriers for chiral amino acids and their sodium and potassium salts

Cited by 14 publications

References 27 publications

Enantioselective separations using chiral supported liquid crystalline membranes

Enantioselective separations using chiral supported liquid crystalline membranes

Silica Colloidal Membranes with Enantioselective Permeability

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

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