Biotechnology and Bioprocess Engineering:BBE

The Korean Society for Biotechnology and Bioengineering (한국생물공학회)
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Molecularly Imprinted Monolithic Stationary Phases for Liquid Chromatographic Separation of Tryptophan and N-CBZ-Phenylalanine Enantiomers

  • Yan, Hong-Yuan (Center for Advanced Bioseparation Technology, Department of Chemical Engineering, Inha University) ;
  • Row, Kyung-Ho (Center for Advanced Bioseparation Technology, Department of Chemical Engineering, Inha University)
  • Published : 2006.08.30
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Abstract

Monolithic molecularly imprinted columns were designed and prepared by an in-situ thermal-initiated copolymerization technique for rapid separation of tryptophan and N- CBZ-phenylalanine enantiomers. The influence of polymerization conditions and separation conditions on the specific molecular recognition ability for enantiomers and diastereomers was investigated. The specious molecular recognition was found to be dependent on the stereo structures and the arrangement of functional groups of the imprinted molecule and the cavities in the molecularly imprinted polymer (MIP). Moreover, hydrogen bonding interactions and hydrophobic interactions played an important role in the retention and separation. Compared to conventional MIP preparation procedures, the present method is very simple, and its macroporous structure has excellent separation properties.

Keywords

References

  1. Huang, X. D., F. Qin, X. M. Chen, Y. Q. Liu, and H. F. Zou (2004) Short columns with molecularly imprinted monolithic stationary phases for rapid separation of diastereomers and enantiomers. J. Chromatogr. B 804: 13-18 https://doi.org/10.1016/j.jchromb.2004.01.015
  2. Liu, Z.-S., Y.-L. Xu, C. Yan, and R.-Y. Gao (2004) Preparation and characterization of molecularly imprinted monolithic column based on 4-hydroxybenzoic acid for the molecular recognition in capillary electrochromatography. Anal. Chim. Acta 523: 243-250 https://doi.org/10.1016/j.aca.2004.07.001
  3. Owens, P. K., L. Karlsson, E. S. M. Lutz, and L. I. Andersson (1999) Molecular imprinting for bio- and pharmaceutical analysis. Trends Anal. Chem. 18: 146-154 https://doi.org/10.1016/S0165-9936(98)00092-2
  4. Chen, W., F. Liu, X. Zhang, K. A. Li, and S. Tong (2001) The specificity of a chlorphenamine-imprinted polymer and its application. Talanta 55: 29-34 https://doi.org/10.1016/S0039-9140(01)00328-9
  5. Zheng, N., Y.-Z. Li, W.-B. Chang, Z.-M. Wang, and T.-J. Li (2002) Sulfonamide imprinted polymers using cofunctional monomers. Anal. Chim. Acta 452: 277-283 https://doi.org/10.1016/S0003-2670(01)01465-9
  6. Spivak, D. and K. J. Shea, (1999) Molecular imprinting of carboxylic acids employing novel functional macroporous polymers. J. Org. Chem. 64: 4627-4634 https://doi.org/10.1021/jo982118s
  7. Matsui, J., I. A. Nicholls, and T. Takeuchi (1998) Molecular recognition in cinchona alkaloid molecular imprinted polymer rods. Anal. Chim. Acta 365: 89-93 https://doi.org/10.1016/S0003-2670(97)00664-8
  8. Bereczki, A., A. Tolokan, G. Horvaia, V. Horvath, F. Lanza, A. J. Hall, and B. Sellergren (2001) Determination of phenytoin in plasma by molecularly imprinted solidphase extraction. J. Chromatogr. A 930: 31-38 https://doi.org/10.1016/S0021-9673(01)01190-6
  9. Ansell, R. J., D. Kriz, and K. Mosbach (1996) Molecularly imprinted polymers for bioanalysis: Chromatography, binding assays and biomimetic sensors. Curr. Opin. Biotechnol. 7: 89-94 https://doi.org/10.1016/S0958-1669(96)80101-7
  10. Kriz, O., O. Ramstrom, and K. Mosbach (1997) Molecular imprinting: new possibilities for sensor technology. Anal. Chem. 69: 345A-349A https://doi.org/10.1021/ac971657e
  11. Liang, C. D., H. Peng, X. Y. Bao, L. H. Nie, S. Z. Yao (1999) Study of a molecular imprinting polymer coated BAW bio-mimic sensor and its application to the determination of caffeine in human serum and urine. Analyst 124: 1781-1785 https://doi.org/10.1039/a905112k
  12. Yoshikawa, M., T. Fujisawa, J. Izumi, T. Kitao, and S. Sakamoto (1998) Molecularly imprinted polymeric membranes involving tetrapeptide EQKL derivatives as chiralrecognition sites toward amino acids. Anal. Chim. Acta 365: 59-67 https://doi.org/10.1016/S0003-2670(98)00092-0
  13. Mayes, A. G. and K. Mosbach (1996) Molecularly imprinted polymer beads: Suspension polymerization using a liquid perfluorocarbon as the dispersing phase. Anal. Chem. 68: 3769-3774 https://doi.org/10.1021/ac960363a
  14. Hosoya, K., K. Yoshizako, Y. Shirasu, K. Kimata, T. Araki, N. Tanaka, and J. Haginaka (1996) Molecularly imprinted uniform-size polymer-based stationary phase for highperformance liquid chromatography Structural contribution of cross-linked polymer network on specific molecular recognition. J. Chromatogr. A 728: 139-147 https://doi.org/10.1016/0021-9673(95)01165-X
  15. Haginaka, J. and C. Kagawa (2002) Uniformly sized molecularly imprinted polymer for d-chlorpheniramine. Evaluation of retention and molecular recognition properties in an aqueous mobile phase. J. Chromatogr. A 948: 77-84 https://doi.org/10.1016/S0021-9673(01)01262-6
  16. Liu, H. Y., K. H. Row, and G. L. Yang (2005) Monolithic molecularly imprinted columns for chromatographic separation. Chromatographia 61: 429-432 https://doi.org/10.1365/s10337-005-0531-x
  17. Hong, S. P., C. H. Lee, S. K. Kim, H. S. Yun, J. H. Lee, and K. H. Row (2004) Mobile phase compositions for ceramide III by normal-phase high-performance liquid chromatography. Biotechnol. Bioprocess Eng. 9: 47-51 https://doi.org/10.1007/BF02949321
  18. Choi, D. Y. and K. H. Row (2004) Theoretical analysis of chromatographic peak asymmetry and sharpness by the moment method using two peptides. Biotechnol. Bioprocess Eng. 9: 495-499 https://doi.org/10.1007/BF02933492
  19. Polyakova, Y., Y. M. Koo, and K. H. Row (2006) Application of ionic liquids as mobile phase modifier in HPLC. Biotechnol. Bioprocess Eng. 11: 1-6 https://doi.org/10.1007/BF02931860
  20. Huang, X. D., H. F. Zou, X. M. Chen, Q. Z. Luo, and L. Kong (2003) Molecularly imprinted monolithic stationary phases for liquid chromatographic separation of enantiomers and diastereomers. J. Chromatogr. A 984: 273-282 https://doi.org/10.1016/S0021-9673(02)01768-5
  21. Yan, H. Y., L. M. Jin, and K. H. Row (2005) Special selectivity of molecularly imprinted monolithic stationary phase. J. Liq. Chromatogr. Relat. Technol. 28: 3147-3155 https://doi.org/10.1080/10826070500330661
  22. Yin, J., G. Yang, and Y. Chen (2005) Rapid and efficient chiral separation of nateglinide and its L-enantiomer on monolithic molecularly imprinted polymers. J. Chromatogr. A 1090: 68-75 https://doi.org/10.1016/j.chroma.2005.06.078
  23. Svec, F., E. C. Peters, D. Sykora, and J. M. J. Frechet (2000) Design of the monolithic polymers used in capillary electrochromatography columns. J. Chromatogr. A 887: 3-29 https://doi.org/10.1016/S0021-9673(99)01232-7
  24. Li, H., Y. Liu, Z. Zhang, H. Liao, L. Nie, and S. Yao (2005) Separation and purification of chlorogenic acid by molecularly imprinted polymer monolithic stationary phase. J. Chromatogr. A 1098: 66-74 https://doi.org/10.1016/j.chroma.2005.08.046