Discrimination between amino acid amide conformers by imprinted polymers

Lepistoe, Matti.; Sellergren, Börje

doi:10.1021/jo00287a006

Cited by 53 publications

(18 citation statements)

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“…942 In addition to chemical shift changes, line widths of NMR signals have also been used to infer complex formation. 913 NMR measurements, including NOE, were used by Lepistö and Sellergren 943 to show the importance of template conformation on the specificity of an imprinted polymer. A problem with fully modelling the environment in the pre-polymerization mixture is the presence of large quantities of cross-linker, which may interfere with the NMR experiment.…”

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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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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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“…Thus, IP-1 interacted equally with the (S)-amino anilide (3)(4)(5), possessing smaller and larger sizes of the α substituent than valine, but the total adsorbabilities of S ad +R ad depended on the steric size of the α substituent. Valine anilide had the largest affinity for MIPs, S ad +R ad =75%, and lower affinities were shown by the substrates with different sizes of side chain substituents (entries 1 and 3).…”

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confidence: 97%

“…Key words (S)-valine anilide; molecular imprinting; chiral recognition; non-imprinted polymer; blank polymer Molecularly imprinted polymers (MIPs) [1][2][3][4] are widely used as a powerful tool for molecular recognition, due to their high adsorbability and selectivity. Although several methods are available to evaluate the performance of MIPs, the measurement of the separating factor (α-value) using an HPLC column filled with a MIP as a stationary phase 5,6) is the most commonly adopted method owing to its simplicity and practical utility.The α-value, however, is affected by many chromatographically experimental factors such as the type of eluent (mobile phase), 7) the substrate, 8) and the theoretical plate number of the column, and it depends on a large number of recycling adsorption-desorption processes in the stationary phase.The batch procedure, 9) on the other hand, directly measures the concentration of the substrate in a reaction mixture, which allows the precise and independent observation of adsorbability and selectivity. Hence, the batch procedure would be amenable in a study of the relationship between the synthesis conditions of a MIP and its ability.…”

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“…Although several methods are available to evaluate the performance of MIPs, the measurement of the separating factor (α-value) using an HPLC column filled with a MIP as a stationary phase 5,6) is the most commonly adopted method owing to its simplicity and practical utility.…”

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A Study of the Various Factors That Affect the Properties of Molecularly Imprinted Polymers

Yasuyama

Matsunaga

Ando

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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We evaluated the adsorbability and selectivity of (S)-valine anilide imprinted molecularly imprinted polymer (MIP) using a batch procedure that is both independent and precise. This study revealed important information about the relationship between the performance of MIPs and experimental factors such as the components of MIP synthesis and a reaction solvent. Herein, we also describe the problems associated with the preparation of a "non-imprinted polymer," which is often used to evaluate the effect of a template molecule, and we propose a new type of reference polymer, "blank polymer." Key words (S)-valine anilide; molecular imprinting; chiral recognition; non-imprinted polymer; blank polymer Molecularly imprinted polymers (MIPs) [1][2][3][4] are widely used as a powerful tool for molecular recognition, due to their high adsorbability and selectivity. Although several methods are available to evaluate the performance of MIPs, the measurement of the separating factor (α-value) using an HPLC column filled with a MIP as a stationary phase 5,6) is the most commonly adopted method owing to its simplicity and practical utility.The α-value, however, is affected by many chromatographically experimental factors such as the type of eluent (mobile phase), 7) the substrate, 8) and the theoretical plate number of the column, and it depends on a large number of recycling adsorption-desorption processes in the stationary phase.The batch procedure, 9) on the other hand, directly measures the concentration of the substrate in a reaction mixture, which allows the precise and independent observation of adsorbability and selectivity. Hence, the batch procedure would be amenable in a study of the relationship between the synthesis conditions of a MIP and its ability.During the course of our trial to evaluate the performance of MIPs using the batch procedure, we gained important information about the relationship between the performance of MIPs and the many factors involved in the processes of synthesis and measurement.In this paper, we report the factors that directly affected the properties of the MIPs. We also describe the problems associated with the preparation of a "blank polymer," which is often used as a reference polymer for the sake of comparison.

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Molekulares Prägen (Imprinting) in vernetzten Materialien mit Hilfe von Matrizenmolekülen – auf dem Weg zu künstlichen Antikörpern

Wulff

1995

Angewandte Chemie

163

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Kann man in organischen oder anorganischen Polymeren Bindungsstellen ähnlich denen in Antikörpern herstellen, die für die molekulare Erkennung und unter Umständen für die Katalyse geeignet sind? In diesem Beitrag wird über ein Verfahren zusammenfassend berichtet, bei dem – ähnlich wie man es sich früher für die Bildung der Antikörper vorstellte – um ein als Matrize (Schablone, Templat) wirkendes Molekül herum in Gegenwart von wechselwirkenden Monomeren vernetzend polymerisiert wird. Nach dem Abtrennen der Matrize bleibt im Polymer ein Abdruck (Imprint) mit zur Wechselwirkung befähigten Gruppen zurück, wobei dessen Form und die Anordnung der Haftgruppen in ihm komplementär zur Struktur des Matrizenmoleküls sind. Der Erfolg des Prägevorgangs kann bei Verwendung chiraler Matrizenmoleküle anhand der Fähigkeit des Polymers zur Spaltung des Racemats der als Matrize verwendeten Verbindung ermittelt werden. Nach umfangreichen Optimierungen des Verfahrens werden heute in der Chromatographie Trennfaktoren α von 4–8 und Basislinien‐Trennungen erhalten. Starkes Interesse gilt auch der Oberflächenprägung von Festkörpern und Monoschichten. Von entscheidender Bedeutung sind in allen Fällen die Struktur der Matrix in den geprägten Materialien und die Funktion der Haftgruppen. Der Mechanismus des Prägens und die molekulare Erkennung von Substraten werden heute schon recht gut verstanden. Zahlreiche praktische Anwendungen derartig hergestellter Produkte werden intensiv bearbeitet. Insbesondere für die chromatographische Racematspaltung sowie die Verwendung als Chemosensoren, als künstliche Antikörper und als selektive Katalysatoren sind technische Anwendungen in Sicht. Von besonderem Interesse ist auch die Verwendung entsprechend hergestellter Verbindungen als Enzymmodelle.

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Discrimination between amino acid amide conformers by imprinted polymers

Cited by 53 publications

References 1 publication

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

A Study of the Various Factors That Affect the Properties of Molecularly Imprinted Polymers

Molekulares Prägen (Imprinting) in vernetzten Materialien mit Hilfe von Matrizenmolekülen – auf dem Weg zu künstlichen Antikörpern

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