Direct separation of ?-hydroxy acid enantiomers by ligand exchange chromatography

Chilmończyk, Zdzisław; ska, Hanna Ksyci; Cybulski, Jacek; Rydzewski, Mariusz; Le, Andrzej

doi:10.1002/(sici)1520-636x(1998)10:9<821::aid-chir8>3.0.co;2-c

Cited by 19 publications

(2 citation statements)

References 18 publications

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“…[5][6][7] Computational calculation studies of enantioseparation have also been reported. [8][9][10][11][12] Several of these studies aimed to understand the chiral recognition mechanisms of chiral stationary phases such as β-cyclodextrin derivatives, 10 L-proline derivatives, 11 and cinchona alkaloids. 12 Recently, a great deal of research on chiral separation using molecular dynamics (MD) simulations [13][14][15][16] and quantitative structure-enantioselective retention relationship calculations 17,18 have been reported.…”

Section: Introductionmentioning

confidence: 99%

Computational Prediction of Diastereomeric Separation Behavior of Fluorescent o-Phthalaldehyde Derivatives of Amino Acids

et al. 2014

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We have developed a convenient method for predicting the LC resolution of amino acid diastereomers through computational calculations. For acquiring experimental data, we derivatized 10 amino acids using o-phthalaldehyde and N-acetyl-L-cysteine as fluorogenic diastereomer-forming reagents and analyzed the diastereomers using reversed-phase LC and fluorescence detection. For theoretical chemical calculations, we used the publicly available semi-empirical calculation software MOPAC2012. Using the obtained experimental and theoretical data, we determined the change in analytical resolution with differences in the structure of the diastereomers. From the results obtained, we concluded that greater conformational change through diastereomeric derivatization induced an increase in the contact area with the stationary phase, leading to higher resolution.

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Section: Introductionmentioning

confidence: 99%

Computational Prediction of Diastereomeric Separation Behavior of Fluorescent o-Phthalaldehyde Derivatives of Amino Acids

et al. 2014

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“…Separation of enantiomers often is difficult and adds significantly to the cost of developing and marketing chiral drugs. Traditional techniques to separate racemic mixtures such as chromatography with chiral stationary phases, − or the use of chiral resolving reagents to form diastereomeric salts that crystallize selectively, generally require high cost and labor-intensive steps that limit their use for large-scale separation of enantiomers. As an alternative approach, we are investigating resolution of racemic pharmaceuticals via crystallization on chiral surfaces as a means to carry out enantioseparation.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Stability and Structure in Three Homochiral and Heterochiral Crystalline Forms of 3-Phenyllactic Acid

Navare

MacDonald

2011

Crystal Growth & Design

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3-Phenyllactic acid (3PLA) is a new example of a chiral compound that can form a conglomerate or a racemic crystal upon crystallization of racemic 3PLA. In this study, homochiral crystals (1), heterochiral racemic crystals (2) (reported here for the first time), and conglomerates (3) of 3PLA were prepared, and the thermal stability, crystal structures, and spectroscopic properties of 1À3 were investigated. Crystals of 1 and 3 formed from aqueous solution as needles (orthorhombic, P2 1 2 1 2 1 ), while crystals of 2 formed from 3:1 hexanesÀethyl acetate as rectangular blocks (monoclinic, P2 1 /c). The pure enantiomer and conglomerates are unusual in that they exhibit slightly greater thermodynamic stability than the racemic form (Δ(ΔH fus ) = 4.0 kJ/mol) despite having considerably lower density (ΔF calc = 3.7%) and less efficient molecular packing in accordance with Wallach's Rule. Considering that molecules of 3PLA adopt essentially identical conformations in the homochiral and heterochiral crystals, the higher stability in crystals of pure enantiomer (1 and 3) results from stronger hydrogen-bonding interactions via homochiral packing as compared to heterochiral packing in racemic crystals (2). 3PLA therefore provides a unique test system to investigate the influence of surface energetics and solvation in biasing homochiral vs heterochiral nucleation to develop methods for enantioseparation via crystallization.

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Enantioselectivity of 3-amino-2-oxazolidinone derivatives with potential psychotropic activity on cellulose tris(4-methylbenzoate) chiral selector

2001

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The behavior of a series of 3-amino-2-oxazolidinone derivatives with a potential hypnotic activity on achiral (octadecylsilane) and chiral (cellulose tris(4-methylbenzoate)) stationary phases was examined. The compounds differed in the composition of a substituted aromatic ring containing different substituents in different positions. It was possible to resolve all the compounds with selectivity 1.11 < or = alpha < or = 2.74. The enantiodifferentiating power of substituents was correlated to their electron donating ability and position in the aromatic ring.

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Direct separation of ?-hydroxy acid enantiomers by ligand exchange chromatography

Cited by 19 publications

References 18 publications

Computational Prediction of Diastereomeric Separation Behavior of Fluorescent o-Phthalaldehyde Derivatives of Amino Acids

Computational Prediction of Diastereomeric Separation Behavior of Fluorescent o-Phthalaldehyde Derivatives of Amino Acids

Investigation of Stability and Structure in Three Homochiral and Heterochiral Crystalline Forms of 3-Phenyllactic Acid

Enantioselectivity of 3-amino-2-oxazolidinone derivatives with potential psychotropic activity on cellulose tris(4-methylbenzoate) chiral selector

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