Chiral separation of 1,1'-bi-2-naphthol and its analogue on molecular imprinting monolithic columns by HPLC.

Two molecular imprinting polymer (MIP) monolithic columns with (S)-(-)-1,1'-bi-2-naphthol and (R)-(+)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol as the templating molecules, respectively, have been prepared by in situ polymerization using 4-vinylpyridine and ethylene dimethacrylate as functional monomer and cross-linker, respectively. The columns with good flow-through properties were obtained by changing the molar ratio of the functional monomer and the template molecule. The effects of mobile-phase composition on separation of enantiomers were systematically investigated. The results indicate that hydrophobic interaction in aqueous solution and hydrogen-bonding interaction in ACN between the enantiomers and polymers could play important roles in the retention and resolution. The effects of chromatographic conditions, such as flow rate, column temperature, sample loading, on the enantioseparation were also studied. Further, these two MIP columns show a cross-reactivity.

[1]  V. B. Kandimalla,et al.  Molecular imprinting: a dynamic technique for diverse applications in analytical chemistry , 2004, Analytical and bioanalytical chemistry.

[2]  Bogusław Buszewski,et al.  Molecularly imprinted polymers: a new tool for separation of steroid isomers. , 2004, Journal of separation science.

[3]  Martha Sibrian-Vazquez,et al.  Molecular imprinting made easy. , 2004, Journal of the American Chemical Society.

[4]  H. Zou,et al.  Short columns with molecularly imprinted monolithic stationary phases for rapid separation of diastereomers and enantiomers. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[5]  J. Haginaka,et al.  Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[6]  P. Sun,et al.  Influence of polymerization temperature on the molecular recognition of imprinted polymers. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[7]  Zhaosheng Liu,et al.  Chiral Separation of Binaphthol Enantiomers on Molecularly Imprinted Polymer Monolith by Capillary Electrochromatography , 2004, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[8]  H. Zou,et al.  Molecular imprinting of nitrophenol and hydroxybenzoic acid isomers: effect of molecular structure and acidity on imprinting , 2003, Journal of molecular recognition : JMR.

[9]  H. Zou,et al.  Molecularly imprinted monolithic stationary phases for liquid chromatographic separation of enantiomers and diastereomers. , 2003, Journal of chromatography. A.

[10]  J. Haginaka,et al.  Uniformly sized molecularly imprinted polymers for bisphenol A and beta-estradiol: retention and molecular recognition properties in hydro-organic mobile phases. , 2003, Journal of pharmaceutical and biomedical analysis.

[11]  W. C. Lee,et al.  Chromatographic resolution of the enantiomers of phenylpropanolamine by using molecularly imprinted polymer as the stationary phase. , 2001, Journal of chromatography. B, Biomedical sciences and applications.

[12]  K. Mosbach,et al.  Molecularly imprinted polymers and their use in biomimetic sensors. , 2000, Chemical reviews.

[13]  K. Shea,et al.  Discrimination between Enantiomers of Structurally Related Molecules: Separation of Benzodiazepines by Molecularly Imprinted Polymers , 2000 .

[14]  J. Haginaka,et al.  Uniform-sized molecularly imprinted polymer for (S)-ibuprofen retention properties in aqueous mobile phases. , 1999, Journal of chromatography. A.

[15]  B. Sellergren.  Polymer- and template-related factors influencing the efficiency in molecularly imprinted solid-phase extractions , 1999 .

[16]  Isao Karube,et al.  Molecularly imprinted polymers for biosensor applications , 1999 .

[17]  P. K. Owens,et al.  Molecular imprinting for bio- and pharmaceutical analysis , 1999 .

[18]  Cong Yu,et al.  Insights into the origins of binding and the recognition properties of molecularly imprinted polymers prepared using an amide as the hydrogen‐bonding functional group , 1998, Journal of molecular recognition : JMR.

[19]  I. Nicholls,et al.  Molecular recognition in cinchona alkaloid molecular imprinted polymer rods , 1998 .

[20]  L. Andersson,et al.  Capillary electrochromatography with molecular imprint-based selectivity for enantiomer separation of local anaesthetics , 1997 .

[21]  L. Andersson,et al.  Capillary Electrochromatography with Predetermined Selectivity Obtained through Molecular Imprinting , 1997 .

[22]  M. Petersson,et al.  Three approaches to enantiomer separation of β‐adrenergic antagonists by capillary electrochromatography , 1997, Electrophoresis.

[23]  K. Mosbach,et al.  Study of the nature of recognition in molecularly imprinted polymers , 1996, Journal of molecular recognition : JMR.

[24]  K Mosbach,et al.  Molecularly imprinted polymer beads:  suspension polymerization using a liquid perfluorocarbon as the dispersing phase. , 1996, Analytical chemistry.

[25]  Klaus Mosbach,et al.  Direct resolution of naproxen on a non-covalently molecularly imprinted chiral stationary phase , 1994 .