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Analytical and Bioanalytical Chemistry

, Volume 378, Issue 8, pp 1907–1912 | Cite as

Chiral resolution of derivatized amino acids using uniformly sized molecularly imprinted polymers in hydro-organic mobile phases

  • Jun HaginakaEmail author
  • Chino Kagawa
Original Paper

Abstract

Uniformly sized molecularly imprinted polymers (MIPs) for Boc-l-Trp were prepared using ethylene glycol dimethacrylate (EDMA) as the cross-linker, and methacylic acid (MAA) and/or 4-vinylpyridine (4-VPY) as the functional monomers or without use of a functional monomer. The MIPs prepared were evaluated using acetonitrile or a mixture of phosphate buffer and acetonitrile as the mobile phase. The Boc-l-Trp-imprinted EDMA polymers can recognize Boc-l-Trp by its molecular shape, and can thus afford the enantioseparation of Boc-Trp. Besides the molecular shape recognition, the hydrophobic interactions with the polymer backbones as well as the hydrogen-bonding interactions of Boc-l-Trp with carboxyl and pyridyl groups in the polymers should work for the retention and recognition of Boc-l-Trp on the imprinted MAA-co-EDMA and 4-VPY-co-EDMA polymers, respectively, in the hydro-organic mobile phase. The hydrogen-bonding interactions seem to become dominant when only acetonitrile is used as the mobile phase. The Boc-l-Trp-imprinted 4-VPY-co-EDMA polymers gave the highest retentivity and enantioselectivity for Boc-Trp among the MIPs prepared. However, the simultaneous use of MAA and 4-VPY was not effective for the enantioseparation of Boc-Trp in a hydro-organic mobile phase. Furthermore, the baseline separation of Boc-Trp enantiomers was attained within 10 min on the Boc-l-Trp-imprinted 4-VPY-co-EDMA polymers under the optimized HPLC conditions.

Keywords

Molecular Imprinting Molecularly imprinted polymer Chiral stationary phase Enantiomer separation Derivatized amino acid 

Notes

Acknowledgements

This work has been supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan to JH.

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Copyright information

© Springer-Verlag 2003

Authors and Affiliations

  1. 1.Faculty of Pharmaceutical SciencesMukogawa Women's UniversityHyogoJapan

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