Tartaric acid derivatives as chiral selectors in liquid chromatography

Heldin, Eva; Lindner, Karl‐Johan; Pettersson, Curt; Lindner, Wolfgang; Rao, R. Nageswara

doi:10.1007/bf02327970

Cited by 60 publications

(27 citation statements)

References 17 publications

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“…Tartaric acid derivatives were used as chiral complexing agents to generate diastereomeric complexes with amino-alcohol enantiomers, facilitating their separation on an achiral stationary phase [32]. The enantiomeric resolution of D-( -)-and L-(+)-ascorbic acid was also demonstrated by this approach and the method was applied to identify vitamin C in medical formulations [31].…”

Section: Solution Phase Molecular Recognition Properties Of Tartratesmentioning

confidence: 99%

“…Even so, 1,19-bi-2-naphthyl di-p-toluenesulfonate, 1,19-bi-2-naphthyl diacetate and 1,19-bi-2-naphthyl dicinnamate enantiomeric mixtures could not been resolved using this method. Chiral liquid stationary phases were prepared on solid supports by immobilizing organic stationary phases prepared by dissolving tartaric acid derivatives in solvents such as hexane or dichloromethane [32]. Both hydrophilic (Nucleosil CN) and hydrophobic (porous graphitic carbon) solid supports were used in a comparative analysis.…”

Section: Solution Phase Molecular Recognition Properties Of Tartratesmentioning

confidence: 99%

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Molecular recognition properties of tartrates and metal‐tartrates in solution and gas phase

Wijeratne

Schug²

2009

J of Separation Science

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Section: Solution Phase Molecular Recognition Properties Of Tartratesmentioning

confidence: 99%

Section: Solution Phase Molecular Recognition Properties Of Tartratesmentioning

confidence: 99%

Molecular recognition properties of tartrates and metal‐tartrates in solution and gas phase

Wijeratne

Schug²

2009

J of Separation Science

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“…and n-dodecyl L-tartrate were prepared according to the literature [20] and their structures were confirmed by 1 H NMR spectroscopy.…”

Section: Reagentsmentioning

confidence: 99%

Preparative enantioseparation of propafenone by counter-current chromatography using di-n -butyl l-tartrate combined with boric acid as the chiral selector

et al. 2013

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This paper extends the research of the utilization of borate coordination complexes in chiral separation by counter-current chromatography (CCC). Racemic propafenone was successfully enantioseparated by CCC with di-n-butyl l-tartrate combined with boric acid as the chiral selector. The two-phase solvent system was composed of chloroform/ 0.05 mol/L acetate buffer pH 3.4 containing 0.10 mol/L boric acid (1:1, v/v), in which 0.10 mol/L di-n-butyl l-tartrate was added in the organic phase. The influence of factors in the enantioseparation of propafenone were investigated and optimized. A total of 92 mg of racemic propafenone was completely enantioseparated using high-speed CCC in a single run, yielding 40-42 mg of (R)- and (S)-propafenone enantiomers with an HPLC purity over 90-95%. The recovery for propafenone enantiomers from fractions of CCC was in the range of 85-90%.

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“…In our current research, we examined two-chiral-component microemulsions assembled with the chiral surfactant DDCV (Rand S-) and the chiral oil dibutyl tartrate (D-and L-) for the separation of pharmaceutical enantiomers. Chiral tartrates have been used in chiral liquid-liquid extraction methods (didodecyl-L-tartrate [22]), as well as in chiral LC (dibutyl L-tartrate [23][24][25]). In addition, racemic dibutyl tartrate was employed as the oil in nonchiral MEEKC work [26,27].…”

Section: Introductionmentioning

confidence: 99%

Two‐chiral‐component microemulsion electrokinetic chromatography–chiral surfactant and chiral oil: Part 1. Dibutyl tartrate

Kahle

Foley

2007

Electrophoresis

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The first simultaneous use of a chiral surfactant and a chiral oil for microemulsion EKC (MEEKC) is reported. Six stereochemical combinations of dodecoxycarbonylvaline (DDCV: R, S, or racemic, 2.00% w/v), racemic 2-hexanol (1.65% v/v), and dibutyl tartrate (D, L, or racemic, 1.23% v/v) were examined as chiral pseudostationary phases (PSPs) for the separation of six pairs of pharmaceutical enantiomers: pseudoephedrine, ephedrine, N-methyl ephedrine, metoprolol, synephrine, and atenolol. Subtle differences were observed for three chromatographic figures of merit (alpha(enant), alpha(meth), k) among the chiral microemulsions; a moderate difference was observed for efficiency (N) and elution range. Dual-chirality microemulsions provided both the largest and smallest enantioselectivities, due to small positive and negative synergies between the chiral microemulsion components. For the ephedrine family of compounds, dual-chiral microemulsions with surfactant and oil in opposite stereochemical configurations provided higher enantioselectivities than the single-chiral component microemulsion (RXX), whereas dual-chiral microemulsions with surfactant and oil in the same stereochemical configurations provided lower enantioselectivities than RXX. Slight to moderate enantioselective synergies were confirmed using a thermodynamic model. Efficiencies observed with microemulsions comprised of racemic dibutyl tartrate or dibutyl-D-tartrate were significantly higher than those obtained with dibutyl-L-tartrate, with an average difference in plate count of about 25 000. Finally, one two-chiral-component microemulsion (RXS) provided significantly better resolution than the remaining one- and two-chiral-component microemulsions for the ephedrine-based compounds, but only slightly better or equivalent resolution for non-ephedrine compounds.

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Tartaric acid derivatives as chiral selectors in liquid chromatography

Cited by 60 publications

References 17 publications

Molecular recognition properties of tartrates and metal‐tartrates in solution and gas phase

Molecular recognition properties of tartrates and metal‐tartrates in solution and gas phase

Preparative enantioseparation of propafenone by counter-current chromatography using di-n -butyl l-tartrate combined with boric acid as the chiral selector

Two‐chiral‐component microemulsion electrokinetic chromatography–chiral surfactant and chiral oil: Part 1. Dibutyl tartrate

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