Separation of tryptophan enantiomers by ligand-exchange chromatography with novel chiral ionic liquids ligand

Chirality

Volumn 26, Issue 3, 2014, Pages 160-165

  Qing, Haiqun ^a   Jiang, Xinyu ^a   Yu, Jingang ^a  

^a CENTRAL SOUTH UNIVERSITY   (China)

Author keywords

chiral ionic liquids; chiral separation; ligand exchange chromatography; tryptophan enantiomers

Indexed keywords

CATION; COPPER ION; IONIC LIQUID; METHANOL; TRYPTOPHAN;

ARTICLE; DRUG STRUCTURE; ION EXCHANGE CHROMATOGRAPHY; PH; PRIORITY JOURNAL;

CHIRAL IONIC LIQUIDS; CHIRAL SEPARATION; LIGAND EXCHANGE CHROMATOGRAPHY; TRYPTOPHAN ENANTIOMERS;

CHROMATOGRAPHY; COPPER; HYDROGEN-ION CONCENTRATION; IONIC LIQUIDS; LIGANDS; METHANOL; STEREOISOMERISM; TRYPTOPHAN;

EID: 84896730452     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22286     Document Type: Article

References (33)

1. Schmid MG, Gübitz G,. Enantioseparation by chromatographic and electromigration techniques using ligand-exchange as chiral separation principle. Anal Bioanal Chem 2011; 400: 2305-2316.
2. Ravikumar M, Varma MS, Raju TS, Suchitra P, Swamy Y,. Enantiomeric separation of moxifloxacin and its (R,R)-isomer by ligand-exchange chiral chromatography. Chromatographia 2009; 69: 85-86.
3. Ma J, Cao J, Ding MJ, Yuan LH, Zhai MJ, Zhang J, Zhang Q, Zhou XM,. Separation of fudosteine on an achiral C-18 column by HPLC with chiral ligand-exchange selectors as mobile phase additives. Acta Chromatogr 2008; 20: 585-594.
4. Bwambok DK, Challa SK, Lowry M, Warner IM,. Amino acid-based fluorescent chiral ionic liquid for enantiomeric recognition. Anal Chem 2010; 82: 5028-5037.
5. Tran CD, Oliveira D, Yu SF,. Chiral ionic liquid that functions as both solvent and chiral selector for the determination of enantiomeric compositions of pharmaceutical products. Anal Chem 2006; 78: 1349-1356.
6. Ward TJ, Ward KD,. Chiral separations: a review of current topics and trends. Anal Chem 2012; 84: 626-635.
7. Ward TJ, Ward KD, Chiral separations: fundamental review 2010. Anal Chem 2010; 82: 4712-4722.
8. Sanaie N, Haynes CA,. Interpreting the effects of temperature and solvent composition on separation of amino-acid racemates by chiral ligand-exchange chromatography. J Chromatogr A 2006; 1104: 164-172.
9. Yan HY, Row KH,. Optimum operational conditions for chiral separation of tryptophan enantiomers using ligand exchange liquid chromatography. Biotechnol Bioproc Eng 2007; 12: 235-241.
10. Liu Q, Wu KK, Tang F, Yao LH, Yang F, Nie Z, Yao SZ,. Amino acid ionic liquids as chiral ligands in ligand exchange chiral separations. Chem Eur J 2009; 15: 9889-9896.
11. Sun XY, Jia YZ, Zeng N, Li FM,. Chiral ligand-exchange chromatography for separation of three stereoisomers of octahydroindole-2-carboxylic acid. Chromatographia 2006; 63: 331-335.
12. Schmid MG,. Chiral metal-ion complexes for enantioseparation by capillary electrophoresis and capillary electrochromatography: A selective review. J Chromatogr A 2012; 1267: 10-16.
13. Berthod A,. Chiral recognition mechanisms in enantiomers separations: a general view. Berlin, Heidelberg: Springer; 2010. p 1-30.
14. Wang SY, Dai Y, Wu JH, Zhou J, Tang J, Tang WH,. Methoxyethylammonium monosubstituted β-cyclodextrin as the chiral selector for enantioseparation in capillary electrophoresis. J Chromatogr A 2013; 1277: 84-92.
15. Cucinotta V, Contino A, Giuffrida A, Maccarrone G, Messina M,. Application of charged single isomer derivatives of cyclodextrins in capillary electrophoresis for chiral analysis. J Chromatogr A 2010; 1217: 953-967.
16. Bezhan C., Enantioseparations by high-performance liquid chromatography using polysaccharide based chiral stationary phases: An overview. Methods Mol Biol 2013; 970: 81-111.
17. Li CK, Kang JW,. Use of macrocyclic antibiotics as the chiral selectors in capillary electrophoresis. Methods Mol Biol 2013; 970: 307-317.
18. Haginaka J, Chiral separations by capillary electrophoresis using proteins as chiral selectors. Methods Mol Biol 2013; 970: 377-392.
19. Paik MJ, Kang JS, Huang BY, Carey JR, Lee WJ,. Development and application of chiral crown ethers as selectors for chiral separation in high-performance liquid chromatography and nuclear magnetic resonance spectroscopy. J Chromatogr A 2013; 1274: 1-5.
20. Li M, Bwambok DK, Fakayode SO, Warner IM,. Chiral ionic liquids in chromatographic separation and spectroscopic discrimination. In, Berthod A, editor. Chiral Recognition in Separation Methods. Berlin Heidelberg: Springer-Verlag; 2010, p 289-329.
21. Han XX, Armstrong DW,. Ionic Liquids in Separations. AccChem Res 2007; 40: 1079-1086.
22. Martín CA, Pino V, Ayala JH, González V, Afonso AM,. Ionic liquids as mobile phase additives in high-performance liquid chromatography with electrochemical detection: Application to the determination of heterocyclic aromatic amines in meat-based infant foods. Talanta 2009; 79: 590-597.
23. Payagala T, Armstrong DW,. Chiral ionic liquids: A compendium of syntheses and applications (2005-2012). Chirality 2012; 24: 17-53.
24. Bica K, Gaertner P,. Applications of chiral ionic liquids. Eur J Org Chem 2008; 19: 3235-3250.
25. Shamsi SA, Danielson ND,. Utility of ionic liquids in analytical separations. J Sep Sci 2007; 30: 1729-1750.
26. Winkel A, Wilhelm R,. New chiral ionic liquids based on enantiopure sulfate and sulfonate anions for chiral recognition. Eur J Org Chem 2010; 58: 17-5824.
27. Ohno H, Fukumoto K,. Amino acid ionic liquids. Acc Chem Res 2007; 40: 1122-1129.
28. Mu XY, Qi L, Zhang HZ, Shen Y, Qiao J, Ma HM,. Ionic liquids with amino acids as cations: Novel chiral ligands in chiral ligand-exchange capillary electrophoresis. Talanta 2012; 97: 349-354.
29. Sun P, Armstrong DW,. Effective enantiomeric separations of racemic primary amines by the isopropyl carbamate-cyclofructan6 chiral stationary phase. J Chromatogr A 2010; 1217: 4904-4918.
30. Hirose KJ, Zhu JY, Nakamura T, Nishioka R, Ueshige T, Tobe Y,. Chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether for enantiomer separation of amino compounds using a normal mobile phase. Chirality 2005; 17: 142-148.
31. Ekborgott KH, Liu YB, Armstrong DW,. Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase. Chirality 1998; 10: 434-483.
32. Yang YX, Li J, Jiang XY,. Chiral ionic liquids as chiral selectors for separation of tryptophan enantiomers by ligand exchange chromatography. J Cent South Univ 2013; 20: 1173-1177.
33. Tao GH, He L, Sun N, Kou Y,. New generation ionic liquids: Cations derived from amino acids. Chem Commun 2005; 35: 62-64.