Molecular recognition on synthetic amorphous surfaces.  The influence of functional group positioning on the effectiveness of molecular recognition

Shea, Keith; Dougherty, T. K.

doi:10.1021/ja00265a046

Cited by 108 publications

(28 citation statements)

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“…Whilst the absolute size and diversity of molecules that can be recognized by a single polymer has not been determined, it is clear that (1) the stereochemistry and (2) the distance between the amine/amide of the substrate are the overriding factors responsible for recognition. This is supported by the description of highly distance-selective polymers (Shea and Dougherty, 1986;Wulff et al, 1986;Norrlow et al, 1987). Recognition and enantiomeric resolution in the system described here therefore required at least two interactions between the substrate and polymer.…”

Section: (mentioning

confidence: 56%

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

O’Shannessy

Andersson

Mosbach

1989

J of Molecular Recognition

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Molecular imprints were prepared using L-phenylalanine anilide as the print molecule and methacrylic acid as the functional monomer. Methacrylic acid interacts ionically with the primary amine of the print molecule and via hydrogen bonding with the amide function. In the HPLC mode such polymers were shown to exhibit efficient enantiomeric resolution of a racemic mixture of the original print molecule. Enantiomeric resolution was shown to be dependent on the ratio of methacrylic acid to print molecule in the pre-polymerization mixture and specific for the presence of both print molecule and functional monomer. Further analyses showed the importance of both the primary amino and amide functions in the correct stereochemistry for recognition and enantiomeric resolution of compounds on such polymers. Other amide derivatives of amino acids including p-nitroanilides, beta-naphthylamides and amides were recognized by such polymers, and enantiomeric resolution was obtained for amide derivatives of amino acid ranging from alanine to tryptophan on a single polymer. The implications of these findings with respect to the mechanism of recognition and the ability to predict enantiomeric resolution of molecules on molecularly imprinted polymers will be discussed.

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Section: (mentioning

confidence: 56%

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

O’Shannessy

Andersson

Mosbach

1989

J of Molecular Recognition

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“…Since the process requires covalent attachment, the template must be prefabricated into a polymerizable derivative of the intended target molecule. Classically, this preorganization approach has utilized template-monomer complexes formed by carboxylic ester linkages, boronate esters, ether linkages, imines, and ketal bonds, among others [53,58,59]. Despite the limitation in the functional groups that can be imprinted using the preorganization approach, effective MIP designs have demonstrated highly selective molecular recognition capabilities [60].…”

Section: Polymer Matrix Designmentioning

confidence: 99%

Biomimetic Molecular Recognition Elements for Chemical Sensing

Jaworski

2012

Biomimetic Approaches for Biomaterials Development

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“…Several trials have been devoted to the preparation of molecular binding sites on imprinted materials by using organic functional groups. [43,[75][76][77][78][79][80][81][82] Shea et al reported molecularly imprinted polymers associated with organic functional groups (-NH 2 or -COOH) and their efficacy in catalysing dehydrofluorination or ester hydrolysis. [83][84][85] Ye et al prepared molecularly imprinted nanoreactors containing -COOH binding sites for regioselective 1,3-dipolar cycloaddition reactions.…”

Section: -Depositedmentioning

confidence: 99%

Preparation and Catalytic Performances of a Molecularly Imprinted Ru‐Complex Catalyst with an NH₂ Binding Site on a SiO₂ Surface

Yang

Weng

Muratsugu

et al. 2011

Chemistry A European J

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A catalyst surface with an active metal site, a shape-selective reaction space, and an NH(2) binding site for o-fluorobenzophenone was designed and prepared by the molecular imprinting of a supported metal complex on a SiO(2) surface. A ligand of a SiO(2)-supported Ru complex that has a similar shape to the product of o-fluorobenzophenone hydrogenation was used as a template. An NH(2) binding site for o-fluorobenzophenone was spatially arranged on the wall of a molecularly imprinted cavity with a similar shape to the template. The structures of the SiO(2)-supported and molecularly imprinted Ru catalysts were characterized in a step-by-step manner by means of solid-state magic angle spinning (MAS) NMR, XPS, UV/Vis, N(2) adsorption, XRF, and Ru K-edge EXAFS. The molecularly imprinted Ru catalyst exhibited excellent shape selectivity for the transfer hydrogenation of benzophenone derivatives. It was found that the NH(2) binding site on the wall of the molecularly imprinted cavity enhanced the adsorption of o-fluorobenzophenone, of which the reduction product was imprinted, whereas there was no positive effect in the case of o-methylbenzophenone, which cannot interact with the NH(2) binding site through hydrogen bonding.

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Molecular recognition on synthetic amorphous surfaces. The influence of functional group positioning on the effectiveness of molecular recognition

Cited by 108 publications

References 0 publications

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

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

Biomimetic Molecular Recognition Elements for Chemical Sensing

Preparation and Catalytic Performances of a Molecularly Imprinted Ru‐Complex Catalyst with an NH₂ Binding Site on a SiO₂ Surface

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Molecular recognition on synthetic amorphous surfaces. The influence of functional group positioning on the effectiveness of molecular recognition

Cited by 108 publications

References 0 publications

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

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

Biomimetic Molecular Recognition Elements for Chemical Sensing

Preparation and Catalytic Performances of a Molecularly Imprinted Ru‐Complex Catalyst with an NH2 Binding Site on a SiO2 Surface

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Preparation and Catalytic Performances of a Molecularly Imprinted Ru‐Complex Catalyst with an NH₂ Binding Site on a SiO₂ Surface