Enantioseparation of phenylsuccinic acid by high speed counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector

Tong, Shengqiang; Yan, Jizhong; Guan, Yong; Lu, Youming

doi:10.1016/j.chroma.2011.06.023

Cited by 45 publications

(34 citation statements)

References 23 publications

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“…Generally, lower separation temperature that suppresses the molecular motion would improve the chiral selectivity while the partition efficiency is decreased [20]. No obvious improved peak resolution was found yet even when the column temperature was decreased to 6–8°C.…”

Section: Resultsmentioning

confidence: 99%

Enantioseparation of dl -tryptophan by spiral tube assembly counter-current chromatography and evaluation of mass transfer rate for enantiomers

Tong¹,

Ito²,

Ma³

2014

Journal of Chromatography A

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Spiral tube assembly counter-current chromatography was successfully applied in enantioseparation of DL-tryptophan using bovine serum albumin as chiral selector. An improved biphasic aqueous-aqueous solvent system 12.0% (w/w) polyethyleneglycol 8000–9.0% (w/w) dibasic potassium phosphate-0.1% ammonia-78.9% water was used as the solvent system for counter-current chromatography, in which bovine serum albumin was predominantly distributed in the lower phase of the two-phase aqueous system. The aqueous-aqueous solvent system gave a very high enantioselectivity for D- and L-tryptophan at α=2.605 along with distribution ratio DD=1.200 and DL=0.461. High peak resolution was obtained for enantioseparation of 2.0 mg of DL-tryptophan by spiral tube assembly counter-current chromatography under room temperature. It was found that 0.1% ammonia added in the aqueous-aqueous solvent system greatly improved the enantioseparations. An unusual extremely broad peak for L-tryptophan was observed during enantioseparations. In order to give an explanation, mass transfer rates of D- and L-enantiomers through the interface between the two phases were measured. It was found that L-tryptophan showed lower mass transfer rate than D-tryptophan. Further discussions were proposed for possible reasons for mass transfer rate difference between the enantiomers.

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Section: Resultsmentioning

confidence: 99%

Enantioseparation of dl -tryptophan by spiral tube assembly counter-current chromatography and evaluation of mass transfer rate for enantiomers

Tong¹,

Ito²,

Ma³

2014

Journal of Chromatography A

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“…It was equipped with a set of three analytical multilayer coils connected in series with a total column volume of 20 mL. The other parameters for the apparatus had been described eariler [11]. The apparatus was installed within a vessel that maintains column temperature by a Model SDC-6 constant-temperature controller (Ningbo Scientz Biotechnology Co. Ltd., Ningbo, China).…”

Section: Methodsmentioning

confidence: 99%

Chiral ligand exchange high-speed countercurrent chromatography: mechanism and application in enantioseparation of aromatic α-hydroxyl acids

Tong

Shen

Cheng

et al. 2014

Journal of Chromatography A

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This work concentrates on the separation mechanism and application of chiral ligand exchange high-speed countercurrent chromatography (HSCCC) in enantioseparations, and comparison with traditional chiral ligand exchange high performance liquid chromatography (HPLC). The enantioseparation of ten aromatic α-hydroxyl acids were performed by these two chromatographic methods. Results showed that five of the racemates were successfully enantioseparated by HSCCC while only three of the racemates could be enantioseparated by HPLC using a suitable chiral ligand mobile phase additive. For HSCCC, the two-phase solvent system was composed of butanol-water (1:1, v/v), to which N-n-dodecyl-L-proline was added in the organic phase as chiral ligand and cupric acetate was added in the aqueous phase as a transition metal ion. Various operation parameters in HSCCC were optimized by enantioselective liquid-liquid extraction. Based on the results of the present studies the separation mechanism for HSCCC was proposed. For HPLC, the optimized mobile phase composed of aqueous solution containing 6 mmol L−1 L-phenylalanine and 3 mmol L−1 cupric sulfate and methanol was used for enantioseparation. Among three ligands tested on a conventional reverse stationary phase column, only one was found to be effective. In the present studies HSCCC presented unique advantages due to its high versatility of two-phase solvent systems and it could be used as an alternative method for enantioseparations.

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“…The parameters for these two sets of apparatus have been described previously [18,19]. CCC centrifuge separation columns were installed in a vessel that maintains column temperature by a Model SDC-6 constant-temperature controller (Ningbo Scientz Biotechnology, Ningbo, China).…”

Section: Apparatusmentioning

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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Enantioseparation of phenylsuccinic acid by high speed counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector

Cited by 45 publications

References 23 publications

Enantioseparation of dl -tryptophan by spiral tube assembly counter-current chromatography and evaluation of mass transfer rate for enantiomers

Enantioseparation of dl -tryptophan by spiral tube assembly counter-current chromatography and evaluation of mass transfer rate for enantiomers

Chiral ligand exchange high-speed countercurrent chromatography: mechanism and application in enantioseparation of aromatic α-hydroxyl acids

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

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