Chiral recognition and separation of beta2-amino acids using non-covalently molecularly imprinted polymers.
Non-covalently molecularly imprinted polymers (MIPs) for beta2-amino acids were prepared for the first time. N-(2-chlorobenzyloxycarbonyl)-(R)-beta2-homophenylalanine (N-2-ClZ-(R)-beta2-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 (alpha= 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-alpha-amino acids and beta-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.
Shim
Yong-Ho
YH
Université P. et M. Curie--Paris VI, UMR 7613 CNRS, Paris, France.
Yilmaz
Ecevit
E
Lavielle
Solange
S
Haupt
Karsten
K
D000596:Amino Acids / Q000302:isolation & purification*; D000818:Animals; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D011108:Polymers; D013237:Stereoisomerism
D000596:Amino Acids; D011108:Polymers