Molecular recognition in synthetic polymers. Enantiomeric resolution of amide derivatives of amino acids on molecularly imprinted polymers

O’Shannessy, Daniel J.; Andersson, Lars I.; Mosbach, Klaus

doi:10.1002/jmr.300020102

Cited by 48 publications

(12 citation statements)

References 10 publications

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“…243,363,378,388,397,398,425,745,856,904,913,925,[999][1000][1001][1002][1003][1004][1005][1006][1007][1008][1009][1010][1011][1012] Partly on account of its UV-activity, the amino acid phenylalanine and its derivatives have proven to be most useful templates in fundamental studies on MIP chromatographic performance, in particular in work by Sellergren et al with phenylalanine anilide, 913,925,1012 which has been an important tool in many studies on aspects of non-covalent molecular imprinting in general.…”

Section: Amino Acids and Derivatives Peptides And Proteinsmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Andersson²,

et al. 2006

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Over 1450 references to original papers, reviews and monographs have herein been collected to document the development of molecular imprinting science and technology from the serendipitous discovery of Polyakov in 1931 to recent attempts to implement and understand the principles underlying the technique and its use in a range of application areas. In the presentation of the assembled references, a section presenting reviews and monographs covering the area is followed by papers dealing with fundamental aspects of molecular imprinting and the development of novel polymer formats. Thereafter, literature describing attempts to apply these polymeric materials to a range of application areas is presented.

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Section: Amino Acids and Derivatives Peptides And Proteinsmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Andersson²,

et al. 2006

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“…For amino acid derivative imprinted polymers, substituents on the amine, 11,23,30 carboxyl group, 28 and amino acid side chain 23 have also shown to be important for recognition on certain imprinted phases. Interestingly, for a Z-L-phenylalanine imprinted phase, the selectivity factor for Z-D,L-alanine was significantly less than for Z-D,L-phenylalanine.…”

Section: Mechanistic Aspects Of Chiral Discrimination 185mentioning

confidence: 99%

Mechanistic Aspects of Chiral Discrimination on a Molecular Imprinted Polymer Phase

O'Brien

Snow

Grinberg³

et al. 1999

Journal of Liquid Chromatography & Related Technologies

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The mechanism of chiral selectivity of a difunctional polymer imprinted with dansyl-L-phenylalanine was investigated using the polymer as an HPLC stationary phase. Temperature studies revealed that the mass transfer of the imprinted enantiomer with the polymer was sluggish at low temperatures, leading to a nonequilibrium migration down the column. Conversely, retention of the non-imprinted enantiomer was controlled by a thermodynamic equilibrium over the entire temperature range of the study. Variation of the structure of the analyte indicated a single leading interaction between both enantiomers of dansyl-phenylalanine and the polymer phase; a hydrogen bonding interaction between the carboxylic acid group of dansyl-phenylalanine and pyridinyl sites on the polymer. Downloaded by [Southern Illinois University] at 08:01 20 December 2014 ORDER REPRINTS 184 O'BRIEN ET AL.Secondary processes contributing to enantioselectivity were also deduced; a hydrogen bonding interaction occurring between the imprinted enantiomer and carboxyl sites on the polymer and a precise steric fit of the amino acid side chain into the imprinted sites.Studies varying the mobile phase hydrogen bond competitor agree with the results obtained by the structural studies.

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“…For comparison, a molar ratio of 1:4:20 (print molecule to functional monomer to cross-linker) was used. This is an optimized recipe for making MIPs using methacrylic acid as the functional monomer (approximately two-to threefold molar equivalents of the functional monomer relative to each polar group of the template) (O'Shannessy et al, 1989;Andersson et al, 1995). Amide MIPs prepared using this recipe normally gave good enantiomeric recognition properties.…”

Section: Polymer Preparationmentioning

confidence: 99%

Insights into the origins of binding and the recognition properties of molecularly imprinted polymers prepared using an amide as the hydrogen-bonding functional group

Mosbach

1998

J. Mol. Recognit.

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Molecularly imprinted polymers (MIPs) prepared using an amide hydrogen-bonding functional monomer (acrylamide) exhibited efficient enantiomeric recognition properties in both organic and aqueous media in the HPLC mode. The results indicate that the amide functional groups formed strong hydrogen-bonding interactions with the template molecule, and specific recognition sites were created within the polymer matrix during the imprinting process. When Boc-L-Trp was used as the template, an MIP prepared in a polar organic solvent (acetonitrile) using acrylamide as the functional monomer showed better enantiomeric recognition of Boc-Trp than the MIPs prepared in the same solvent using an acidic (methacrylic acid) or a basic (2-vinylpyridine) functional monomer or a combination of an acidic and a basic functional monomer (methacrylic acid + 2-vinylpyridine). Our results indicate that in organic media the degree of retention of the sample molecule on the imprinted polymer was controlled by hydrogen-bonding interactions between the sample molecule and the polymer, while in aqueous media it was determined to a considerable extent by hydrophobic interactions. In both media the shape, size and the nature of the hydrogen-bonding groups of the sample molecules were all important factors in determining the enantiomeric and substrate selectivity. In the aqueous media, however, the hydrophobicity of the sample molecules was also found to play an important role.

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Molecular recognition in synthetic polymers. Enantiomeric resolution of amide derivatives of amino acids on molecularly imprinted polymers

Cited by 48 publications

References 10 publications

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Mechanistic Aspects of Chiral Discrimination on a Molecular Imprinted Polymer Phase

Insights into the origins of binding and the recognition properties of molecularly imprinted polymers prepared using an amide as the hydrogen-bonding functional group

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