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Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether-β-cyclodextrin as chiral selector.
J Sep Sci. 2020 Feb; 43(3):681-688.JS

Abstract

Acetyltropic acid is an important synthetic intermediate for preparation of tropane alkaloid derivatives, which can be used as anticholinergic drugs, deliriants, and stimulants. In the present work, acetyltropic acid was successfully enantioseparated by countercurrent chromatography using sulfobutyl ether-β-cyclodextrin as chiral selector. A biphasic solvent system composed of n-butyl acetate/n-hexane/0.1 mol/L citrate buffer at pH = 2.2 containing 0.1 mol/L of sulfobutyl ether-β-cyclodextrin (7:3:10, v/v) was selected, which produced a suitable distribution ratio DS = 1.14, DR = 2.31 and a high enantioseparation factor α = 2.03. Baseline separation was achieved for preparative enantioseparation of 50 mg of racemic acetyltropic acid. A method for chiral analysis of acetyltropic acid by conventional reverse phase liquid chromatography with hydroxylpropyl-β-cyclodextrin as mobile phase additive was established, and formation constants of inclusion complex were determined. It was found that different substituted β-cyclodextrin should be selected for enantioseparation of acetyltropic acid by countercurrent chromatography and reverse phase liquid chromatography.

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Authors+Show Affiliations

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

MeSH

Countercurrent DistributionMolecular ConformationStereoisomerismbeta-Cyclodextrins

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31714009

Citation

Qiu, Xujun, et al. "Enantioseparation of Acetyltropic Acid By Countercurrent Chromatography With Sulfobutyl Ether-β-cyclodextrin as Chiral Selector." Journal of Separation Science, vol. 43, no. 3, 2020, pp. 681-688.

Qiu X, Sun W, Wang C, et al. Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether-β-cyclodextrin as chiral selector. J Sep Sci. 2020;43(3):681-688.

Qiu, X., Sun, W., Wang, C., Yan, J., & Tong, S. (2020). Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether-β-cyclodextrin as chiral selector. Journal of Separation Science, 43(3), 681-688. https://doi.org/10.1002/jssc.201900730

Qiu X, et al. Enantioseparation of Acetyltropic Acid By Countercurrent Chromatography With Sulfobutyl Ether-β-cyclodextrin as Chiral Selector. J Sep Sci. 2020;43(3):681-688. PubMed PMID: 31714009.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether-β-cyclodextrin as chiral selector. AU - Qiu,Xujun, AU - Sun,Wenyu, AU - Wang,Chaoyue, AU - Yan,Jizhong, AU - Tong,Shengqiang, Y1 - 2019/11/28/ PY - 2019/07/24/received PY - 2019/10/10/revised PY - 2019/11/08/accepted PY - 2019/11/13/pubmed PY - 2020/10/30/medline PY - 2019/11/13/entrez KW - acetyltropic acid KW - countercurrent chromatography KW - cyclodextrins KW - enantioseparation KW - liquid chromatography SP - 681 EP - 688 JF - Journal of separation science JO - J Sep Sci VL - 43 IS - 3 N2 - Acetyltropic acid is an important synthetic intermediate for preparation of tropane alkaloid derivatives, which can be used as anticholinergic drugs, deliriants, and stimulants. In the present work, acetyltropic acid was successfully enantioseparated by countercurrent chromatography using sulfobutyl ether-β-cyclodextrin as chiral selector. A biphasic solvent system composed of n-butyl acetate/n-hexane/0.1 mol/L citrate buffer at pH = 2.2 containing 0.1 mol/L of sulfobutyl ether-β-cyclodextrin (7:3:10, v/v) was selected, which produced a suitable distribution ratio DS = 1.14, DR = 2.31 and a high enantioseparation factor α = 2.03. Baseline separation was achieved for preparative enantioseparation of 50 mg of racemic acetyltropic acid. A method for chiral analysis of acetyltropic acid by conventional reverse phase liquid chromatography with hydroxylpropyl-β-cyclodextrin as mobile phase additive was established, and formation constants of inclusion complex were determined. It was found that different substituted β-cyclodextrin should be selected for enantioseparation of acetyltropic acid by countercurrent chromatography and reverse phase liquid chromatography. SN - 1615-9314 UR - https://www.unboundmedicine.com/medline/citation/31714009/Enantioseparation_of_acetyltropic_acid_by_countercurrent_chromatography_with_sulfobutyl_ether_β_cyclodextrin_as_chiral_selector_ DB - PRIME DP - Unbound Medicine ER -