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Issue 12, 2004
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Chiral recognition and separation of β2-amino acids using non-covalently molecularly imprinted polymers

Yong-Ho Shim,a  Ecevit Yilmaz,b  Solange Laviellea  and  Karsten Haupt*c 
Author affiliations

* Corresponding authors

a Université P. et M. Curie—Paris VI, UMR 7613 CNRS, Case 182, 4 Place Jussieu, 75005 Paris, France

b Lund University, Center for Chemistry and Chemical Engineering, Pure and Applied Biochemistry, P.O. Box 124, 22100 Lund, Sweden

c Université de Technologie de Compiègne, UMR CNRS 6022, B.P. 20529, 60205 Compiègne, France
E-mail: karsten.haupt@utc.fr

Abstract

Non-covalently molecularly imprinted polymers (MIPs) for β2-amino acids were prepared for the first time. N-(2-chlorobenzyloxycarbonyl)-(R)-β2-homophenylalanine (N-2-ClZ-(R)-β2-HPhe) was imprinted with methacrylic acid (MAA) and/or 4-vinylpyridine (4-VPy) as the functional monomers, with ethylene glycol dimethacrylate (EDMA) as the cross-linker. The MIPs made with different ratios of MAA ∶ 4-VPy were studied in HPLC mode. The results show that MIPs made with 4-VPy yielded the best chiral separation factor (α = 1.86) for the template molecule. The importance for an efficient separation of pi-stacking interactions between the MIPs and the template molecule is demonstrated. Racemates of Z-α-amino acids and β-amino acid analogues of the template were either not or poorly resolved by the MIPs, thus demonstrating the close three-dimensional complementarity of the MIPs' recognition sites with the template.

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Publication details

The article was received on 29 Jun 2004, accepted on 07 Sep 2004 and first published on 13 Oct 2004


Article type: Paper
DOI: 10.1039/B409836F
Citation: Analyst, 2004,129, 1211-1215
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    Chiral recognition and separation of β2-amino acids using non-covalently molecularly imprinted polymers

    Y. Shim, E. Yilmaz, S. Lavielle and K. Haupt, Analyst, 2004, 129, 1211
    DOI: 10.1039/B409836F

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