Enantioselective separation of ketoconazole enantiomers by membrane extraction

Separation and Purification Technology

Volumn 79, Issue 1, 2011, Pages 63-71

  Wang, Zhao ^a   Cai, Changqun ^a   Lin, Yongtao ^a   Bian, Yongru ^a   Guo, Hongqin ^a   Chen, Xiaoming ^a  

^a XIANGTAN UNIVERSITY   (China)

Author keywords

Biphasic recognition; Chiral selector; Hollow fiber membrane; l Isopentyl tartrate; Sulfobutylether cyclodextrin

Indexed keywords

AQUEOUS PHASE; AQUEOUS PHASIS; BIPHASIC; BIPHASIC SYSTEMS; CHIRAL SELECTOR; ENANTIOSELECTIVE; ENANTIOSELECTIVE SEPARATION; EXPERIMENTAL CONDITIONS; FEED PHASE; HOLLOW FIBER; HOLLOW FIBER MEMBRANE; HOLLOW FIBER MEMBRANE MODULES; HOLLOW FIBER MEMBRANES; HYDROPHOBIC AND HYDROPHILIC; L-ISOPENTYL TARTRATE; MASS TRANSFER PERFORMANCE; MEMBRANE EXTRACTION; NEW PROCESS; OPTICAL PURITY; ORGANIC PHASE; SEPARATION SYSTEMS; SHELL-SIDE; STRIP PHASE;

CHIRALITY; ENANTIOMERS; ENANTIOSELECTIVITY; FIBERS; HYDROPHILICITY; HYDROPHOBICITY; MATHEMATICAL MODELS;

MEMBRANES;

EID: 79955599934     PISSN: 13835866     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.seppur.2011.03.013     Document Type: Article

References (57)

1. S.A. Mostafavi, and R.T. Foster Pharmacokinetics of metoprolol enantiomers following single and multiple administration of racemate in rat Int. J. Pharm. 202 2000 97 102 (Pubitemid 30466234)
2. D. Joshua, K. Anjanette, K. Preeti, S.S. David, and J.G. Andrew Enantioselective separation on a naturally chiral surface J. Am. Chem. Soc. 126 2004 14988 114994
3. E. Fogassy, M. Nógrádi, D. Kozma, G. Egri, E. Pálovics, and V. Kiss Optical resolution methods Org. Biomol. Chem. 4 2006 3011 3030 (Pubitemid 44186846)
4. N.F. Ghazali, F.C. Ferreira, A.J.P. White, and A.G. Livingston Chiral separation by enantioselective inclusion complexation-organic solvent nanofiltration Desalination 199 2006 398 400 (Pubitemid 44161279)
5. H.B. Ding, P.W. Carr, and E.L. Cussler Racemic leucine separation by hollow-fiber extraction AIChE J. 38 1992 1493 1498
6. S.B. Lee, D.T. Mitchell, L. Trofin, T.K. Nevanen, H. Söderlund, and C.R. Martin Antibody-based bio-nanotube membranes for enantiomeric drug separations Science 296 2002 2198 2200 (Pubitemid 34680299)
7. S.S. Jung, W. Dongmok, L. Hyoyoung, I.J. Sung, O. Jinho, J.J. Young, and K. Kimoon A homochiral metal-organic porous material for enantioselective separation and catalysis Nature 404 2000 982 986
8. J.F. Hang, Y. Ishii, Y. Furukawa, and L. Deng Synthesis and application of chiral α-amino acids by kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides with modified cinchona alkaloid catalysts ACS Symp. Ser. 1009 2009 265 287
9. K. Makino, Y. Hiroki, and Y. Hamada Dynamic kinetic resolution catalyzed by Ir axially chiral phosphine catalyst: asymmetric synthesis of anti aromatic β-hydroxy-α-amino acid esters J. Am. Chem. Soc. 127 2005 5784 5785 (Pubitemid 40577625)
10. J. Crosby Synthesis of optically active compounds: a large scale perspective Tetrahedron 47 1991 4789 4846
11. K. Makino, T. Goto, Y. Hiroki, and Y. Hamada Stereoselective synthesis of anti-β-hydroxy-α-amino acids through dynamic kinetic resolution Angew. Chem. Int. Ed. 116 2004 900 902
12. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization Am. Chem. Soc. 109 1987 5765 5780
13. I. Ojima, N. Clos, and C. Bastos Recent advances in catalytic asymmetric reactions promoted by transition metal complexes Tetrahedron 45 1989 6901 6939 (Pubitemid 20003538)
14. J.E. Rekoske Chiral separation AIChE J. 47 2001 2 5
15. N. Demirel, Y. Bulut, and H. Hosgoren Enantioselective transport and liquid-liquid extraction of amino acids as their potassium and sodium salts by optically active diaza-18-crown-6 ethers Chirality 16 2004 347 350 (Pubitemid 38833313)
16. R.M.C. Viegas, C.A.M. Afonso, J.G. Crespo, and I.M. Coelhoso Modelling of the enantio-selective extraction of propranolol in a biphasic system Sep. Purif. Technol. 53 2007 224 234 (Pubitemid 46108661)
17. J. Koska, and C.A. Haynes Modelling multiple chemical equilibria in chiral partition systems Chem. Eng. Sci. 56 2001 5853 5864 (Pubitemid 33023767)
18. M. Colera, A.M. Costero, P. Gaviña, and S. Gil Synthesis of chiral 18-crown-6 ethers containing lipophilic chains and their enantiomeric recognition of chiral ammonium picrates Tetrahedron: Asymmetry 16 2005 2673 2679 (Pubitemid 41116660)
19. K. Erdal, K. Aysegul, S. Abdulkadir, and Y. Mustafa Synthesis of new chiral calyx[4]arene diamide derivatives for liquid phase extraction of α-amino acid methylesters Tetrahedron: Asymmetry 17 2006 1514 1520
20. B. Schuur, A.J. Hallett, J.G.M. Winkelman, J.G. de Vries, and H.J. Heeres Scalable enantioseparation of amino acid derivatives using continuous liquid-liquid extraction in a cascade of centrifugal contactor separators Org. Process Res. Dev. 13 2009 911 914
21. B. Schuur, J. Floure, A.J. Hallett, J.G.M. Winkelman, J.G. deVries, and H.J. Heeres Continuous chiral separation of amino acid derivatives by enantioselective liquid-liquid extraction in centrifugal contactor separators Org. Process Res. Dev. 12 2008 950 955
22. B. Schuur, J.G.M. Winkelman, and H.J. Heeres Equilibrium studies on enantioselective liquid-liquid amino acid extraction using a cinchona alkaloid extractant Ind. Eng. Chem. Res. 47 2008 10027 10033
23. B. Schuur, J.G.M. Winkelman, J.G. de Vries, and H.J. Heeres Experimental and modeling studies on the enantio-separation of 3,5-dinitrobenzoyl-(R),(S)- leucine by continuous liquid-liquid extraction in a cascade of centrifugal contactor separators Chem. Eng. Sci. 65 2010 4682 4690
24. K.W. Tang, Y.Y. Chen, and J.J. Liu Resolution of zopiclone enantiomers by biphasic recognition chiral extraction Sep. Purif. Technol. 62 2008 683 688
25. K.W. Tang, L.T. Song, Y.B. Liu, Y. Pan, and X.Y. Jiang Separation of flurbiprofen enantiomers by biphasic recognition chiral extraction Chem. Eng. J. 158 2010 411 417
26. K.W. Tang, J.M. Yi, Y.B. Liu, X.Y. Jiang, and Y. Pan Enantioselective separation of R,S-phenylsuccinic acid by biphasic recognition chiral extraction Chem. Eng. Sci. 64 2009 4081 4088
27. K.W. Tang, Y.Y. Chen, K.L. Huang, and J.J. Liu Enantioselective resolution of chiral aromatic acids by biphasic recognition chiral extraction Tetrahedron: Asymmetry 18 2007 2399 2408
28. K.W. Tang, J.M. Yi, K.L. Huang, and G.L. Zhang Biphasic recognition chiral extraction: a novel method for separation of mandelic acid enantiomers Chirality 21 2009 390 395
29. K.W. Tang, G.L. Zhang, K.L. Huang, Y.J. Li, and J.M. Yi Resolution of α-cyclohexyl-mandelic acid enantiomers by two-phase (O/W) recognition chiral extraction Sci. China Ser. B-Chem. 50 2007 764 769
30. K.K. Sirkar Membranes, phase interfaces, and separations: novel techniques and membranes - an overview Ind. Eng. Chem. Res. 47 2008 5250 5266
31. S. Schlosser, R. Kertész, and J. Marták Recovery and separation of organic acids by membrane-based solvent extraction and pertraction - an overview with a case study on recovery of MPCA Sep. Purif. Technol. 41 2005 237 266
32. W.H. Pirkle, and W.E. Bowen Preparative separation of enantiomers using hollow-fiber membrane technology Tetrahedron: Asymmetry 5 1994 773 776 (Pubitemid 24175374)
33. F. Valenzuela, C. Basualto, C. Tapia, and J. Sapag Application of hollow-fiber supported liquid membranes technology to the selective recovery of a low content of copper from a Chilean mine water J. Membr. Sci. 155 1999 163 168 (Pubitemid 29076655)
34. R.S. Juang, R.H. Huang, and R.T. WU Separation of citric and lactic acids in aqueous solutions by solvent extraction liquid membrane processes J. Membr. Sci. 136 1997 89 99
35. Y.J. Wang, G.S. Luo, and Y.Y. Dai Research on removal of sulfanilic acid from water with membrane extraction Mod. Chem. Ind. 10 2000 31 33
36. M. Pinelo, G. Jonsson, and A.S. Meyer Membrane technology for purification of enzymatically produced oligosaccharides: molecular and operational features affecting performance Sep. Purif. Technol. 70 2009 1 11
37. N. Masanori, K. Satoshi, S. Kyoichi, S. Kazuyuki, and S. Takanobu Chiral separation of dl-tryptophan using porous membranes containing multilayered bovine serum albumin crosslinked with glutaraldehyde J. Chromatogr. A 822 1998 53 58
38. Y.C. Xiao, H.M. Lim, T.S. Chung, and R. Rajagopalan Acetylation of β-cyclodextrin surface-functionalized cellulose dialysis membranes with enhanced chiral separation Langmuir 23 2007 12990 12996
39. N. Papo, and Y. Shai Effect of drastic sequence alteration and d-amino acid incorporation on the membrane binding behavior of lytic peptides J. Biochem. 43 2004 6393 6403 (Pubitemid 38697539)
40. D.W. Armstrong, and H.L. Jin Enrichment of enantiomers and other isomers with aqueous liquid membranes containing cyclodextrin carriers Anal. Chem. 59 1987 2237 2241
41. P. Hadik, L. Kotsis, M.E. Bódogh, L.P. Szabó, and E. Nagy Lactic acid enantioseparation by means of porous ceramic disc and hollow fiber organic membrane Sep. Purif. Technol. 41 2005 299 304
42. P. Dzygiel, P. Wieczorek, J.A. Jonsson, and M. Milewska Separation of amino acid enantiomers using supported liquid membrane extraction with chiral phosphates and phosphonates Tetrahedron 55 1999 9923 9932 (Pubitemid 29366862)
43. A. Maximini, H. Chmiel, H. Holdik, and N.W. Maier Development of a supported liquid membrane process for separating enantiomers of N-protected amino acid derivatives J. Membr. Sci. 276 2006 221 231
44. T. Gumí, C. Torras, R. Garcia-Valls, and C. Palet Activated composite membranes containing the chiral carrier N-hexadecyl-l-hydroxyproline. Description of morphology and performance J. Ind. Eng. Chem. Res. 44 2005 7696 7700 (Pubitemid 41452470)
45. J.F. Liu, G.B. Jiang, Y.G. Chi, Y.Q. Cai, Q.X. Zhou, and J.T. Hu Use of ionic liquids for liquid-phase microextraction of polycyclic aromatic hydrocarbons Anal. Chem. 75 2003 5870 5876
46. S. Dilmaghanian, J.G. Gerber, and S.G. Filler Enantioselectivity of inhibition of cytochrome P450 3A4 (CYP3A4) by ketoconazole: testosterone and methadone as substrates Chirality 16 2004 79 85 (Pubitemid 38134070)
47. P. Camps, J. Ginesta, D. Mauleón, and G. Carganico Stereoselective synthesis of both enantiomers of ketoconazole from (R)- and (S)-epichlorohydrin Tetrahedron: Asymmetry 6 1995 1283 1294
48. M. Steensma, N.J.M. Kuipers, A.B. De Haan, and G. Kwant Identification of enantioselective extractants for chiral separation of amines and aminoalcohols Chirality 18 2006 314 328 (Pubitemid 43672680)
49. Y. Abe, T. Shoji, S. Fukui, M. Sasamoto, and H. Nishizawa Enantioselective distribution of amino-alcohols in a liquid-liquid two-phase system containing dialkyl l-tartrate and boric acid Chem. Pharm. Bull. 43 1995 262 265
50. L.F.B. Malta, Y. Cordeiro, L.W. Tinoco, C.C. Campos, M.E. Medeiros, and O.A.C. Antunes Recognition mechanism of d- and l-tryptophan enantiomers using 2-hydroxypropyl-α- or β-cyclodextrins as chiral selectors Tetrahedron: Asymmetry 19 2008 1182 1188 (Pubitemid 351766714)
51. E. Schneiderman, and A.M. Stalcup Cyclodextrins: a versatile tool in separation science J. Chromatogr. B 745 2000 83 102 (Pubitemid 30497221)
52. S. Touil, S. Tingry, S. Bouchtalla, and A. Deratani Selective pertraction of isomers using membranes having fixed cyclodextrin as molecular recognition sites Desalination 193 2006 291 298 (Pubitemid 44160458)
53. Y. Tanaka, and S. Terabe Enantiomer separation of acidic racemates by capillary electrophoresis using cationic and amphoretic β-cyclodextrins as chiral selectors J. Chromatogr. A 781 1997 151 160 (Pubitemid 27458710)
54. O. Zerbinati, F. Trotta, C. Giovannoli, C. Baggiani, G. Giraudi, and A. Vanni New derivatives of cyclodextrins as chiral selectors for the capillary electrophoretic separation of dichlorprop enantiomers J. Chromatogr. A 810 1998 193 200 (Pubitemid 28288241)
55. J.T.F. Keurentjes, L.J.W.M. Nabuurs, and E.A. Vegter Liquid membrane technology for the separation of racemic mixtures J. Membr. Sci. 113 1996 351 360 (Pubitemid 26156024)
56. E. Heldin, K.J. Lindner, C. Pettersson, W. Lindner, and R. Rao Tartaric acid derivatives as chiral selectors in liquid chromatography Chromatographia 32 1991 407 416
57. W. Lindner Enantioselective chromatography: selection of chiral recognition models Mikrochimica Acta 104 1991 113 128