Enantioseparation of phenylsuccinic acid enantiomers based on aqueous two-phase system with ethanol/ammonium sulfate: Phase diagrams optimization and partitioning experiments

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 81, Issue 3-4, 2015, Pages 475-484

  Wang, Jun ^a   Chen, Xiaoqing ^a,b   Jiao, Feipeng ^a  

^a CENTRAL SOUTH UNIVERSITY   (China)

^b Resource Conserving and Environment Friendly Society and Ecological Civilization 2011 Collaborative Innovation Center of Hunan Province   (China)

Author keywords

Aqueous two phase system; Enantioseparation; Hydroxypropyl cyclodextrin; Optimization; Phase diagram; Phenylsuccinic acid enantiomers

Indexed keywords

EID: 84937521680     PISSN: 09230750     EISSN: 15731111     Source Type: Journal    
DOI: 10.1007/s10847-015-0477-z     Document Type: Article

References (42)

1. Horvath, J.D., Koritnik, A., Kamakoti, P., Sholl, D.S., Gellman, A.J.: Enantioselective separation on a naturally chiral surface. J. Am. Chem. Soc. 126, 14988-14994 (2004)
2. Kolemen, S., Cakmak, Y., Kostereli, Z., Akkaya, E.U.: Atropisomeric dyes: axial chirality in orthogonal BODIPY oligomers. Org. Lett. 16, 660-663 (2014)
3. Maier, N.M., Franco, P., Lindner, W.: Separation of enantiomers: needs, challenges, perspectives. J. Chromatogr. A 906, 3-33 (2001)
4. Tang, W., Muderawan, I.W., Ng, S.-C., Chan, H.S.O.: Enantio-selective separation in capillary electrophoresis using a novel mono-6A-propylammonium-β-cyclodextrin as chiral selector. Anal. Chim. Acta 555, 63-67 (2006)
5. Gavioli, E., Maier, N.M., Minguillón, C., Lindner, W.: Preparative enantiomer separation of dichlorprop with a cinchona-derived chiral selector employing centrifugal partition chromatography and high-performance liquid chromatography: a comparative study. Anal. Chem. 76, 5837-5848 (2004)
6. Chen, B., Deng, J., Yang, W.: Hollow two-layered chiral nano-particles consisting of optically active helical polymer/silica: preparation and application for enantioselective crystallization. Adv. Funct. Mater. 21, 2345-2350 (2011)
7. Guangyou, Z., Yuquing, L., Zhaohui, W., Nohira, H., Hirose, T.: Resolution of β-aminoalcohols and 1,2-diamines using fractional crystallization of diastereomeric salts of dehydroabietic acid. Tetrahedron Asymmetry 14, 3297-3300 (2003)
8. Maftouh, M., Granier-Loyaux, C., Chavana, E., Marini, J., Pradines, A., Heyden, Y.V., Picard, C.: Screening approach for chiral separation of pharmaceuticals: Part III. Supercritical fluid chromatography for analysis and purification in drug discovery. J. Chromatogr. A 1088, 67-81 (2005)
9. Binanzer, M., Hsieh, S.-Y., Bode, J.W.: Catalytic kinetic resolution of cyclic secondary amines. J. Am. Chem. Soc. 133, 19698-19701 (2011)
10. Sunsandee, N., Leepipatpiboon, N., Ramakul, P., Pancharoen, U.: The selective separation of (S)-amlodipine via a hollow fiber supported liquid membrane: Modeling and experimental verification. Chem. Eng. J. 180, 299-308 (2012)
11. Schmid, M., Gübitz, G.: Enantioseparation by chromatographic and electromigration techniques using ligand-exchange as chiral separation principle. Anal. Bioanal. Chem. 400, 2305-2316 (2011)
12. Huang, B.-Y., Chen, Y.-C., Wang, G.-R., Liu, C.-Y.: Preparation and evaluation of a monolithic molecularly imprinted polymer for the chiral separation of neurotransmitters and their analogues by capillary electrochromatography. J. Chromatogr. A 1218, 849-855 (2011)
13. Lacour, J., Goujon-Ginglinger, C., Torche-Haldimann, S., Jodry, J.J.: Efficient enantioselective extraction of tris(diimine)ruthenium(ii) complexes by chiral, lipophilic TRISPHAT anions. Angew. Chem. Int. Ed. 39, 3695-3697 (2000)
14. Colera, M., Costero, A.M., Gaviña, P., Gil, S.: Synthesis of chiral 18-crown-6 ethers containing lipophilic chains and their enantiomeric recognition of chiral ammonium picrates. Tetrahedron Asymmetry 16, 2673-2679 (2005)
15. Tan, B., Luo, G., Wang, J.: Extractive separation of amino acid enantiomers with co-extractants of tartaric acid derivative and Aliquat-336. Sep. Purif. Technol. 53, 330-336 (2007)
16. Tang, K., Zhang, P., Li, H.: Experimental and model study on the multiple chemical equilibrium for reactive extraction of ibuprofen enantiomers with HP-β-CD as hydrophilic selector. Process Biochem. 46, 1817-1824 (2011)
17. Snyder, S.E., Carey, J.R., Pirkle, W.H.: Biphasic enantioselective partitioning studies using small-molecule chiral selectors. Tetrahedron 61, 7562-7567 (2005)
18. Verkuijl, B.J.V., Minnaard, A.J., de Vries, J.G., Feringa, B.L.: Chiral separation of underivatized amino acids by reactive extraction with palladium-BINAP complexes. J. Org. Chem. 74, 6526-6533 (2009)
19. Tang, F., Zhang, Q., Ren, D., Nie, Z., Liu, Q., Yao, S.: Functional amino acid ionic liquids as solvent and selector in chiral extraction. J. Chromatogr. A 1217, 4669-4674 (2010)
20. Tang, K., Song, L., Liu, Y., Pan, Y., Jiang, X.: Separation of flurbiprofen enantiomers by biphasic recognition chiral extraction. Chem. Eng. J. 158, 411-417 (2010)
21. Sellergren, B., Ekberg, B., Albertsson, P.-Å., Mosbach, K.: Preparative chiral separation in an aqueous two-phase system by a few counter-current extractions. J. Chromatogr. A 450, 277-280 (1988)
22. Tang, K., Yi, J., Liu, Y., Jiang, X., Pan, Y.: Enantioselective separation of R, S-phenylsuccinic acid by biphasic recognition chiral extraction. Chem. Eng. Sci. 64, 4081-4088 (2009)
23. Li, Z., Teng, H., Xiu, Z.: Aqueous two-phase extraction of 2,3-butanediol from fermentation broths using an ethanol/ammonium sulfate system. Process Biochem. 45, 731-737 (2010)
24. Azevedo, A.M., Rosa, P.A.J., Ferreira, I.F., Aires-Barros, M.R.: Chromatography-free recovery of biopharmaceuticals through aqueous two-phase processing. Trends Biotechnol. 27, 240-247 (2009)
25. Li, Z., Teng, H., Xiu, Z.: Extraction of 1,3-propanediol from glycerol-based fermentation broths with methanol/phosphate aqueous two-phase system. Process Biochem. 46, 586-591 (2011)
26. Vázquez-Villegas, P., Aguilar, O., Rito-Palomares, M.: Study of biomolecules partition coefficients on a novel continuous separator using polymer-salt aqueous two-phase systems. Sep. Purif. Technol. 78, 69-75 (2011)
27. Wu, Y., Wang, Y., Zhang, W., Han, J., Liu, Y., Hu, Y., Ni, L.: Extraction and preliminary purification of anthocyanins from grape juice in aqueous two-phase system. Sep. Purif. Technol. 124, 170-178 (2014)
28. Azevedo, A.M., Gomes, A.G., Rosa, P.A.J., Ferreira, I.F., Pisco, A.M.M.O., Aires-Barros, M.R.: Partitioning of human antibodies in polyethylene glycol-sodium citrate aqueous two-phase systems. Sep. Purif. Technol. 65, 14-21 (2009)
29. 4. J. Chem. Technol. Biotechnol. 88, 1545-1550 (2013)
30. 4 aqueous two-phase system by a two-step extraction. Process Biochem. 45, 1664-1671 (2010)
31. Frerix, A., Müller, M., Kula, M.-R., Hubbuch, J.: Scalable recovery of plasmid DNA based on aqueous two-phase separation. Biotechnol. Appl. Biochem. 42, 57-66 (2005)
32. Guedes de Andrade, E., de Siqueira Cardoso Silva, M., Brandão Haga, R., Carvalho Santos, V., Pessoa, A., Rangel-Yagui, C.D.O.: Extraction of clavulanic acid using aqueous two-phase micellar system. Biotechnol. Appl. Biochem. 58, 103-108 (2011)
33. Wade, K.L., Ito, Y., Ramarathnam, A., Holtzclaw, W.D., Fahey, J.W.: Purification of active myrosinase from plants by aqueous two-phase counter-current chromatography. Phytochem. Anal. 26, 47-53 (2015)
34. Bi, P.-Y., Chang, L., Mu, Y.-L., Liu, J.-Y., Wu, Y., Geng, X., Wei, Y.: Separation and concentration of baicalin from Scutellaria baicalensis Georgi extract by aqueous two-phase flotation. Sep. Purif. Technol. 116, 454-457 (2013)
35. Arai, T., Kuroda, H.: Distribution behavior of some drug enantiomers in an aqueous two-phase system using counter-current extraction with protein. Chromatographia 32, 56-60 (1991)
36. Chen, X., Liu, L., Jiao, F., Wang, Z.: Extraction of phenylalanine enantiomers by aqueous two phase systems containing combinatorial chiral selector. Chin. J. Chem. 30, 965-969 (2012)
37. Xing, J.-M., Li, F.-F.: Chiral separation of mandelic acid by temperature-induced aqueous two-phase system. J. Chem. Technol. Biotechnol. 87, 346-350 (2012)
38. Han, J., Wang, Y., Yu, C., Li, C., Yan, Y., Liu, Y., Wang, L.: Separation, concentration and determination of chloramphenicol in environment and food using an ionic liquid/salt aqueous two-phase flotation system coupled with high-performance liquid chromatography. Anal. Chim. Acta 685, 138-145 (2011)
39. Loftsson, T., Brewster, M.E.: Cyclodextrins as functional excipients: methods to enhance complexation efficiency. J. Pharm. Sci. 101, 3019-3032 (2012)
40. Zhao, S., Liu, Y.-M.: Electrophoretic separation of tryptophan enantiomers in biological samples. Electrophoresis 22, 2769-2774 (2001)
41. Tang, K., Miao, J., Zhou, T., Song, L.: Equilibrium studies on reactive extraction of naproxen enantiomers using hydrophilic β-cyclodetrin derivatives extractants. J. Incl. Phenom. Macrocycl. Chem. 69, 213-220 (2011)
42. Owens, P., Fell, A., Coleman, M., Berridge, J.: Complexation of voriconazole stereoisomers with neutral and anionic derivatised cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 38, 133-151 (2000)