Chiral ligand exchange high-speed countercurrent chromatography: Mechanism and application in enantioseparation of aromatic α-hydroxyl acids

Journal of Chromatography A

Volumn 1360, Issue , 2014, Pages 110-118

  Tong, Shengqiang ^a,b   Shen, Mangmang ^a   Cheng, Dongping ^a   Zhang, Yamei ^a   Ito, Yoichiro ^b   Yan, Jizhong ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b NATIONAL HEART LUNG AND BLOOD INSTITUTE   (United States)

Author keywords

Aromatic hydroxyl acids; Chiral ligand exchange; Enantioseparation; High speed countercurrent chromatography; Separation mechanism

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; LIGANDS; METAL IONS; ORGANIC ACIDS; SEPARATION; SPEED; TRANSITION METAL COMPOUNDS; TRANSITION METALS;

CHIRAL LIGAND EXCHANGES; ENANTIOSEPARATIONS; HIGH-SPEED COUNTER CURRENT CHROMATOGRAPHY; HYDROXYL ACIDS; SEPARATION MECHANISM;

LIQUID CHROMATOGRAPHY;

2 CHLOROMANDELIC ACID; 3 CHLOROMANDELIC ACID; 4 BROMOMANDELIC ACID; 4 METHOXYMANDELIC ACID; ALPHA CYCLOHEXYLMANDELIC ACID; ALPHA CYCLOPENTYLMANDELIC ACID; AROMATIC ALPHA HYDROXYL ACID; AROMATIC CARBOXYLIC ACID; ATROLACTIC ACID; BUTANOL; COPPER ACETATE; HEXANE; MANDELIC ACID; MANDELIC ACID DERIVATIVE; METAL ION; N N DODECYL LEVO PROLINE; SOLVENT; UNCLASSIFIED DRUG; VANILMANDELIC ACID; WATER;

ANALYTICAL EQUIPMENT; AQUEOUS SOLUTION; ARTICLE; CENTRIFUGE; CHIRAL CHROMATOGRAPHY; COUNTER CURRENT CHROMATOGRAPHY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION EXCHANGE CHROMATOGRAPHY; LIQUID LIQUID EXTRACTION; ORGANIC CHEMISTRY; PRIORITY JOURNAL; PROCESS OPTIMIZATION; RACEMIC MIXTURE; SEPARATION TECHNIQUE; ULTRAVIOLET DETECTOR; CHEMISTRY; ISOLATION AND PURIFICATION; PROCEDURES; STEREOISOMERISM;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUNTERCURRENT DISTRIBUTION; LIQUID-LIQUID EXTRACTION; MANDELIC ACIDS; SOLVENTS; STEREOISOMERISM;

EID: 84906787145     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2014.07.057     Document Type: Article

References (24)

1. Hare P.E., Gil-Av E. Separation of d and l amino acids by liquid chromatography: use of chiral eluants. Science 1979, 204:1226-1228.
2. Gübitz G., Jellenz W., Santi W. Resolution of the optical isomers of underivatized amino acids on chemically bonded chiral phases by ligand exchange chromatography. J. Liq. Chromatogr. 1981, 4:701-712.
3. Gübitz G., Jellenz W., Santi W. Separation of the optical isomers of amino acids by ligand-exchange chromatography using chemically bonded chiral phases. J. Chromatogr. 1981, 203:377-384.
4. Davankov V.A., Rogozhin S.V. Ligand chromatography as a novel method for the investigation of mixed complexes: stereoselective effects in α-amino acid copper (II) complexes. J. Chromatogr. 1971, 60:280-283.
5. Wernicke R. Separation of underivatised amino acid enantiomers by means of a chiral solvent-generated phase. J. Chromatogr. Sci. 1985, 23:39-48.
6. Natalini B., Sardella R., Ianni F. Enantioseparations by high-performance liquid chromatography based on chiral ligand-exchange. Chiral Separations-Methods and Protocols 2013, 191-208. Humana Press, New York, NY United States.
7. Ito Y., Bowman R.L. Countercurrent chromatography: liquid-liquid partition chromatography without solid support. Science 1970, 167:281-283.
8. Ito Y. Efficient preparative counter-current chromatography with a coil planet centrifuge. J. Chromatogr. 1981, 214:122-125.
9. Ito Y., Sandlin J.L., Bowers W.G. High-speed preparative counter-current chromatography with a coil planet centrifuge. J. Chromatogr. 1982, 244:247-258.
10. Ito Y., Conway W.D. Development of countercurrent chromatography. Anal. Chem. 1984, 56:534A-554A.
11. Ito Y. Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. J. Chromatogr. A 2005, 1065:145-168.
12. Guzlek H., Wood P.L., Janaway L. Performance comparison using the GUESS mixture to evaluate counter-current chromatography instruments. J. Chromatogr. A 2009, 1216:4181-4186.
13. Hopmann E., Goll J., Minceva M. Sequential centrifugal partition chromatography: a new continuous chromatographic technology. Chem. Eng. Technol. 2012, 35:72-82.
14. Völkl J., Arlt W., Minceva M. Theoretical study of sequential centrifugal partition chromatography. AIChE J. 2013, 59:241-249.
15. Foucault A.P. Enantioseparations in counter-current chromatography and centrifugal partition chromatography. J. Chromatogr. A 2001, 906:365-378.
16. Perez E., Minguillon C. Counter-current chromatography in the separation of enantiomers. Chiral Separation Techniques: A Practical Approach 2007, 369-397. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
17. Zheng Y., Yan J.Z., Tong S.Q. Research progress on countercurrent chromatography in enantioseparations. Chin. J. Pharm. Anal. 2013, 33:536-543.
18. Takeuchi T., Horikawa R., Tanimura T. Complete resolution of dl-isoleucine by droplet counter-current chromatography. J. Chromatogr. 1984, 284:285-288.
19. Takeuchi T., Horikawa R., Tanimura T., Kabasawa Y. Resolution of dl-Valine by countercurrent solvent extraction with continuous sample feeding. Sep. Sci. Technol. 1990, 25:941-951.
20. Ohfune Y., Kurokawa N., Higuchi N., Saito M., Hashimoto M., Tanaka T. an efficient one-step reductive N-monoalkylation of .ALPHA.-amino acids. Chem. Lett. 1984, 13:441-444.
21. Tong S.Q., Zhang H., Shen M.M., Ito Y., Yan J.Z. Enantioseparation of mandelic acid derivatives by high performance liquid chromatography with substituted β-cyclodextrin as chiral mobile phase additive and evaluation of inclusion complex formation. J. Chromatogr. B 2014, 962:44-51.
22. Koska J., Haynes C.A. Modelling multiple chemical equilibria in chiral partition systems. Chem. Eng. Sci. 2001, 56:5853-5864.
23. Conway W.D. Counter-current Chromatography: Apparatus, Theory, and Application 1990, VCH publisher, New York.
24. Nishizawa H., Tahara K., Hayashida A., Abe Y. Continuous separation method with liquid particle extractor: enantioseparation of (±)-mandelic acid. Anal. Sci. 1993, 9:611-615.