Ligand-exchange chromatography of amino acid race-mates on separon gels containing L-proline or L-hydroxyproline groupings

Yamskov, I. A.; Berezin, B. B.; Davankov, V. A.; Zolotarev, Yu. A.; Dostavalov, I.N.; Myasoedov, N. F.

doi:10.1016/s0021-9673(00)88104-2

Cited by 26 publications

(7 citation statements)

References 8 publications

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“…For example, in 1971, Davankov and Rogozhin developed the first asymmetric sorbent for HPLC through the reaction of a chloromethylated styrene copolymer with L‐proline, accomplishing the resolution of (±)‐proline by means of the reversible formation of complexes with Cu 2+ ions (CSP‐ 2 , Figure ). In 1979 Hare and Gil‐Av reported the separation of non‐derivatized enantiomeric amino acid employing a chiral complex of proline‐copper(II) (molar ratio 2 : 1) as aqueous eluent on an ion‐exchange column …”

Section: Chiral Stationary Phases For High Performance Liquid Chromatmentioning

confidence: 99%

Fundamental Developments of Chiral Phase Chromatography in Connection with Enantioselective Synthesis of β‐Amino Acids

Vargas-Caporali

Juaristi

2017

Israel Journal of Chemistry

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A few decades ago, the enantiomeric purities of chiral compounds were usually determined by comparison of experimental optical rotations or by preparation of diastereomeric derivatives followed by analysis of their 1H NMR spectra. This situation changed when Emanuel Gil‐Av, Binyamin Feibush and Rosita Charles‐Sigler achieved the separation of single enantiomers from racemic α‐amino acids by means of a chiral stationary phase. Indeed, chiral chromatography allowed a direct comparison of chromatograms obtained from enantiopure samples with those recorded with their racemates. With the aim of celebrating the relevance of Gil‐Av's achievement, this review also presents several applications of chiral chromatography in the area of asymmetric synthesis of β‐amino acids.

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Section: Chiral Stationary Phases For High Performance Liquid Chromatmentioning

confidence: 99%

Fundamental Developments of Chiral Phase Chromatography in Connection with Enantioselective Synthesis of β‐Amino Acids

Vargas-Caporali

Juaristi

2017

Israel Journal of Chemistry

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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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“…Driven by the rapid development in asymmetric organic synthesis leading to chiral drugs, food additives, fragrances, agricultural chemicals, and many other important compounds, and as a solution to the analytical requirements of agencies regulating their use, the spectrum of suitable selectors has expanded significantly during the last three decades. They currently include a wide variety of species such as metal ion complexes [1,6], small molecules [2,7,8], crown ethers [9], cyclodextrins [10], macrocyclic glycopeptides [11], proteins [12], as well as synthetic [13,14] and modified natural polymers [15].…”

Section: Introductionmentioning

confidence: 99%

Polymer‐bound cellulose phenylcarbamate derivatives as chiral stationary phases for enantioselective HPLC

Ling

Brahmachary

et al. 2003

J of Separation Science

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Novel chiral stationary phases (CSP) have been prepared by coating the internal surface of monodisperse macroporous poly(2-aminoethyl methacrylate-co-ethylene dimethacrylate) beads with dimethylphenylcarbamate derivatives of regenerated cellulose. The coating was achieved either by simple adsorption or by chemical bonding using a diisocyanate linker. Separation of enantiomers in normal-phase HPLC mode was used to evaluate the enantioselectivity of all CSPs. The influence of the properties of the polymer support such as pore size, pore volume, and content of the amine functionalities, reaction and separation conditions such as weight ratio of modified cellulose selector to polymer beads, amount of diisocyanate crosslinker, and the composition of the mobile phase on chiral discrimination and chromatographic resolution were also systematically investigated. The CSPs prepared by chemical anchoring were more stable and a wider range of solvents including dichloromethane could be used for the separations. Compared to the coated-type CSPs, the chemically bonded stationary phases enabled the enantioseparations of a larger number of racemates and exhibited enantioselectivity fully comparable to their counterparts prepared using porous silica as a support. However, the benefits of tailored macroporous polymer supports demonstrated earlier with brush-type CSPs did not enhance the performance of the chiral stationary phases prepared from cellulose-based selectors.

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Ligand-exchange chromatography of amino acid race-mates on separon gels containing L-proline or L-hydroxyproline groupings

Cited by 26 publications

References 8 publications

Fundamental Developments of Chiral Phase Chromatography in Connection with Enantioselective Synthesis of β‐Amino Acids

Fundamental Developments of Chiral Phase Chromatography in Connection with Enantioselective Synthesis of β‐Amino Acids

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

Polymer‐bound cellulose phenylcarbamate derivatives as chiral stationary phases for enantioselective HPLC

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