Optically Selective Adsorption of α-Amino Acids on Montmorillonite-Cu-1-Lysine Complexes in High-Pressure Liquid Chromatography

Tsvetkov, Faina; Mingelgrin, U.

doi:10.1346/ccmn.1987.0350510

Cited by 13 publications

(7 citation statements)

References 30 publications

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“…The use of spray-dried, quasi-spherical particles of montmorillonite (SP-bentonite) as a packing material for high-pressure liquid chromatography (HPLC) columns was reported by Mingelgrin and Tsvetkov (1985) and by Tsvetkov and Mingelgrin (1987). The spraydried particles were composed of clay platelets, the orientation of which relative to each other within the particle closely resembled their orientation in the suspension used to generate the SP-bentonite.…”

Section: Introductionmentioning

confidence: 99%

“…This orientation contrasts with the parallel, face-to-face arrangement of platelets typical of bentonite powder. Chromatographic separations by SP-bentonite columns have been used to study the interaction of many organic monomers with montmorillonite (Mingelgrin and Tsvetkov, 1985;Tsvetkov, 1985;Tsvetkov and Mingelgrin, 1987). Cross-linked hydroxy-Al-montmorillonite (A1-CLM), developed by , made available a new adsorbent having a rigid, welldefined structure.…”

Section: Introductionmentioning

confidence: 99%

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Cross-Linked Hydroxy-Al-Montmorillonite as a Stationary Phase in Liquid Chromatography

Tsvetkov

1990

Clays and clay miner.

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Abstract--Quasi-spherical particles (7-tzm mean diameter) were prepared from cross-linked hydroxy-A1-montmorillonite (basal spacing = 15.3 and 18.6 A) by spray-drying. These particles (SP-CLM) were used as a packing material for columns in high-pressure liquid chromatography (HPLC). Aromatic phosphate esters, chlorosubstituted phenyl-ureas, monosubstituted benzenes, and the o-, m-, and p-isomers of disubstituted benzenes were separated on the columns, using isopropanol and hexane. Alkyl and alkoxy groups in the solute molecules sterically hindered the interaction of these molecules with the solid phase. The retention of the isomers of disubstituted benzenes that possess one electronegative (or dipolar) and one nonpolar substituent increased in the order: o-< m-< p-. In contrast, for all investigated disubstituted benzenes containing two electronegative (or dipolar) substituents, the o-isomer was retained on the 18.6-A SP-CLM more strongly than the m-and p-isomers. The chromatographic data suggest that the strength of the interaction of phenolic groups with the solid phase increased with the acidity of these groups. The o-isomers of phenols that contained an additional electronegative (or dipolar) substituent displayed an exceptionally strong adsorption. The capacity of the o-isomers of disubstituted benzenes containing two electronegative (or dipolar) substituents to form chelates with A1 probably was responsible for the strong retention of such o-isomers compared with the retention of the corresponding m-and p-isomers.Cross-linked hydroxy-Al-montmorillonite acted as a strong and selective adsorbent for many families of organic compounds. It was used successfully as the solid phase in HPLC separations with eluents ranging from nonpolar (e.g., hexane) to highly polar (e.g., water).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cross-Linked Hydroxy-Al-Montmorillonite as a Stationary Phase in Liquid Chromatography

Tsvetkov

1990

Clays and clay miner.

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“…Among these, it is worth mentioning the amino acids proline, hydroxyproline (Davankov and Kurganov, 1983;Yamskov et al, 1981), cysteine (Natalini et al, , 2008b(Natalini et al, , 2008c, histidine Watanabe, 1983), phenylalanine (Wan et al, 1997;Wernicke, 1995), alanine (Tsvetkov and Mingelgrin, 1987), lysine (Tsvetkov and Mingelgrin, 1987), isoleucine (Huang et al, 2005), and penicillamine (Ôi et al, 1995), and few amino alcohols carrying a phenylglycinol (Hyun et al, 2003(Hyun et al, , 2004, leucinol (Hyun and Ryoo, 1996;Hyun et al, 2002), or pyrrolidinemethanol (Natalini et al, 2007) residual as the basic scaffold.…”

Section: Introductionmentioning

confidence: 99%

S-Trityl-(R)-Cysteine, a Multipurpose Chiral Selector for Ligand-Exchange Liquid Chromatography Applications

Sardella

Ianni

Lisanti

et al. 2015

Critical Reviews in Analytical Chemistry

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The stratification of 0.040-0.050 g of S-trityl-(R)-cysteine ((R)-STC) onto a conventional ODS phase produces a very effective (α and RS up to 5.71 and 12.09, respectively) and stable (more than 30 days of repeated analysis) chiral ligand-exchange chromatography (CLEC) coated chiral stationary phase (C-CSP). With a few specific exceptions, a (R) < (S) enantiomer elution order can be easily predicted. The (R)-STC-based C-CSP can be successfully exploited also at a preparative level for enantioisolations of CNS active amino acids (AAs), with a racemate loadability up to 0.015 g for single injection. The CLEC (R)-STC-based system can be helpful in monitoring the presence of (R)-AAs in edible products and other organic materials, thus contributing to evaluating product quality and diagnosing subclinical pathological states in animals and humans. Very profitably, molecular modeling-based computer-assisted classification analyses can reveal the actual enantioseparation ability of the (R)-STC phase towards a specific compound.

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“…High pressure liquid chromatography (HPLC) has been used to investigate the interaction of a wide variety of aromatic compounds and amino acids with montmorillonite (Mingelgrin and Tsvetkov, 1985;Tsvetkov and Mingelgrin, 1987) and with cross-linked hydroxy-aluminum-montmorillonite (AI-CLM) (Tsvetkov et al, 1990). The purpose of the present study is to use HPLC to probe the interaction of substituted benzenes with potassium halide treated montmorillonites (KTM) as a function of the method of preparation of the KTM and the nature of its exchangeable cation.…”

Section: Introductionmentioning

confidence: 99%

Potassium Halide-Treated Montmorillonite (KTM) as a Solid Phase in Liquid Chromatography

Tsvetkov

Heller-Kallai

Mingelgrin

1993

Clays and clay miner.

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Abstract--Columns for high pressure liquid chromatography were prepared from spray dried samples of montmorillonite that were heated with potassium halides (KTM) to increase both the cation density on the clay surfaces and the expandability of the interlayers. Some of the clay samples were exchanged with Cu before and/or after the potassium halide treatment.Retention of nitrobenzene and its chloro and methyl derivatives, of methyl substituted phenols and of nitrophenols on these columns was studied, using eluents ranging in polarity from hexane to isopropanol. The retention of the aromatic molecules depends on their specific interaction with active sites on the clay surfaces and on steric effects which limit access to the clay interlayers. Both penetrability and surface interaction are controlled by the composition and method of preparation of the solid phase and by the polarity of the mobile phase. Very strong adsorption of some eluates and efficient chromatographic separations between related substituted benzenes were achieved. Mixtures of the three isomers of cresol, chloronitrobenzene, nitrotoluene or nitrophenol were completely resolved by a judicious combination of solid phase and eluent.

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Optically Selective Adsorption of α-Amino Acids on Montmorillonite-Cu-1-Lysine Complexes in High-Pressure Liquid Chromatography

Cited by 13 publications

References 30 publications

Cross-Linked Hydroxy-Al-Montmorillonite as a Stationary Phase in Liquid Chromatography

Cross-Linked Hydroxy-Al-Montmorillonite as a Stationary Phase in Liquid Chromatography

S-Trityl-(R)-Cysteine, a Multipurpose Chiral Selector for Ligand-Exchange Liquid Chromatography Applications

Potassium Halide-Treated Montmorillonite (KTM) as a Solid Phase in Liquid Chromatography

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