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Enantioseparation of Three Isomeric α-(chlorophenyl)propanoic Acid by Countercurrent Chromatography and Investigation of Chlorine Substituent Through Characterization of Inclusion Interaction

Enantioseparation of Three Isomeric α-(chlorophenyl)propanoic Acid by Countercurrent Chromatography and Investigation of Chlorine Substituent Through Characterization of Inclusion Interaction

Yang Jin, Huawei Lv, Xingchu Gong, Wenyu Sun, Shanshan Zhao, Xiang Wang, Meng Luo, Jizhong Yan, Shengqiang Tong

J Chromatogr A. 2019 Oct 25;1604:460471.

PMID: 31471133

Abstract:

The influence of chlorine substituents in chiral separation of three racemic 2-(chlorophenyl)propanoic acids by countercurrent chromatography using hydroxypropyl-β-cyclodextrin as a chiral additive were mainly investigated in the present paper, including 2-(2-chlorophenyl)propanoic acids, 2-(3-chlorophenyl)propanoic acids and 2-(4-chlorophenyl)propanoic acids. The influences of chromatographic conditions on the retention behavior were studied by enantioselective liquid-liquid extraction experiments using the methodology of response surface It was found that 2-(3-chlorophenyl)propanoic acids could be successfully chiral separated by countercurrent chromatography, while no resolution was achieved for racemic 2-(2-chlorophenyl)propanoic acids and 2-(4-chlorophenyl)propanoic acids under optimized separation conditions. The formation of 1:1 stoichiometric inclusion compounds between 2-(3-chlorophenyl)propanoic acids and HP-β-CD was determined by UV spectra measurements. The inclusion constants for 2-(3-chlorophenyl)propanoic acids and HP-β-CD were determined by the Benesi-Hildebrand equation. Meanwhile, the inclusion constants of 2-(3-chlorophenyl)-propanoic acid enantiomer and HP-β-CD were obtained by the pesudophase retention equation in countercurrent chromatography. Furthermore, the inclusion interactions of the three racemates with HP-β-CD were also investigated by the molecular docking. The results obtained from UV spectra measurements and molecular docking showed that the racemate with chlorine substituents in meta-position presented the highest enantiorecognition while the racemates with chlorine substituents in ortho-position had the lowest enantiorecognition. The above results further indicated that forming a stable inclusion complex between racemate and chiral selector is a prerequisite for a successful enantioseparation and at the same time, the difference in inclusion capacity between the two enantiomers is also essential for the enantioseparation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS7931243	1-(3-Chlorophenyl)-1H-pyrazol-4-ylboronic acid			Price

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