Mechanism of change in enantiomer migration order of enantioseparation of tartaric acid by ligand exchange capillary electrophoresis with Cu(II) and Ni(II)–<scp>D</scp>‐quinic acid systems

Aizawa, SenâIchi; Kodama, Shuji

doi:10.1002/elps.201100512

Cited by 10 publications

(6 citation statements)

References 13 publications

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“…D‐tartarate is selectively coordinated to the 1:1 complex to give the 1:1:1 Cu(II)–D‐quinate–D‐tartarate ternary complex, while L‐tartarate is selectively bound to the 1:2 and 1:3 complexes to form the 1:2:1 ternary complex. The number of ligands affects mobility of the compounds and enables the separation of enantiomers via capillary electrophoresis . The alleviation of Al toxicity to plants by tartaric acid also depends on the type of its enantiomer.…”

Section: Why Include Enantiomers?mentioning

confidence: 99%

Natural Occurrence of Enantiomers of Organic Compounds Versus Phytoremediations: Should Research on Phytoremediations Be Revisited? A Mini‐review

et al. 2013

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Decontamination of polluted soils using plants is based on the ability of plant species (including transgenic plants) to enhance bioavailability of pollutants in the rhizosphere and support growth of pollutant-degrading microorganisms via root exudation and plant species-specific composition of the exudates. In this work, we review current knowledge of enantiomers of low-molecular-weight (LMW) organic compounds with emphasis on their use in phytoremediation. Many research studies have been performed to search for plants suitable for decontamination of polluted soils. Nevertheless, the natural occurrence of L- versus D-enantiomers of dominant compounds of plant root exudates which play different roles in the complexation of heavy metals, chemoattraction, and support of pollutant-degrading microorganisms were not included in these studies. D-enantiomers of aliphatic organic acids and amino acids or L-enantiomers of carbohydrates occur in high concentrations in root exudates of some plant species, especially under stress, and are less stimulatory for plants to extract heavy metals or for rhizosphere microflora to degrade pollutants compared with L-enantiomers (organic acids and amino acids) or D-carbohydrates. Determining the ratio of L- versus D-enantiomers of organic compounds as a criterion of plant suitability for decontamination of polluted soils and development of other types of bioremediation technologies need to be subjects of future research.

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Section: Why Include Enantiomers?mentioning

confidence: 99%

Natural Occurrence of Enantiomers of Organic Compounds Versus Phytoremediations: Should Research on Phytoremediations Be Revisited? A Mini‐review

et al. 2013

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“…A chiral ligand‐exchange system was also supported by spectroscopic techniques in order to rationalize migration and complexation phenomena. Aizawa and Kodama noted reversal of EMO of tartrate in ligand‐exchange CE using D ‐quinic acid as selector as a function of the metal ions Cu(II) and Ni(II) . 13 C‐NMR spectroscopy and circular dichroism experiments revealed that at fixed Cu(II) concentrations 1:1, 1:2, and 1:3 Cu(II)–D‐quinate complexes were formed with increasing concentrations of D ‐quinic acid.…”

Section: Investigation Of Analyte–selector Complex Structurementioning

confidence: 99%

Recent advances in electrodriven enantioseparations

Jáč

Scriba

2012

J of Separation Science

109

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Capillary electromigration techniques have developed into significant analytical separation tools especially for enantioseparations. While CE can be considered a mature technique as documented by its wide applications, CEC is still in a developmental state despite many research efforts. The success of stereospecific CE separation methods is due to the high specificity and flexibility of the technique as well as the availability of many types of chiral selectors. Thus, numerous methods have been developed for the analysis of chiral compounds in chemical, biochemical, pharmaceutical, environmental, and forensic sciences. However, most reported applications deal with pharmaceuticals. The search for new chiral selectors also continued despite the fact that most applications were performed using cyclodextrins. Furthermore, CE has been combined with spectroscopic and molecular modeling studies in attempts to understand the interactions between chiral selectors and analytes. The present review focuses on recent examples of mechanistic aspects of capillary enantioseparations with regard to mathematical modeling of enantioseparations, investigations of the analyte-complex structures as well as new chiral selectors and applications of chiral analyses by CE and CEC. It covers the literature published between January 2011 and August 2012.

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“…The same result was obtained by using a BGE (pH 5.0) containing 20 mM acetate buffer, 20 mM D-quinic acid, and 10 mM CuSO 4 except that the migration order of D-and L-TA was reversed [21]. This reversal of enantiomer migration order of DL-TA on ligand exchange CE can be explained by the change in coordination selectivity for D-and L-TA in the Cu(II)−D-quinic acid system based on the compositions of the complexes formed in BGE [22]. Using Al(III), Mn(II), and Zn(II) ions as the central metal ion, peaks of the three ␣-hydroxy acids were not detected.…”

Section: Enantioseparation Of Three ␣-Hydroxy Acids With a Singular Cmentioning

confidence: 99%

Enantioseparation of α‐hydroxy acids by chiral ligand exchange CE with a dual central metal ion system

et al. 2012

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Using two kinds of central metal ions in a background electrolyte, ligand exchange CE was investigated for the simultaneous enantioseparation of dl-malic, dl-tartaric, and dl-isocitric acids. Ligand exchange CE with 100 mM d-quinic acid as a chiral selector ligand and 10 mM Cu(II) ion as a central metal ion could enantioseparate dl-tartaric acid but not dl-malic acid or dl-isocitric acid. A dual central metal ion system containing 0.5 mM Al(III) ion in addition to 10 mM Cu(II) ion in the background electrolyte enabled the simultaneous enantioseparation of the three α-hydroxy acids. These results suggest that the use of a dual central metal ion system can be useful for enantioseparation by ligand exchange CE.

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Mechanism of change in enantiomer migration order of enantioseparation of tartaric acid by ligand exchange capillary electrophoresis with Cu(II) and Ni(II)–D‐quinic acid systems

Cited by 10 publications

References 13 publications

Natural Occurrence of Enantiomers of Organic Compounds Versus Phytoremediations: Should Research on Phytoremediations Be Revisited? A Mini‐review

Natural Occurrence of Enantiomers of Organic Compounds Versus Phytoremediations: Should Research on Phytoremediations Be Revisited? A Mini‐review

Recent advances in electrodriven enantioseparations

Enantioseparation of α‐hydroxy acids by chiral ligand exchange CE with a dual central metal ion system

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