Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solut
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Molecularly Imprinted Polymers (MIPs) Against Uracils : Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography Andrew J. Hall1, Panagiotis Manesiotis, Jakob T. Mossing and Börje Sellergren Institut für Anorganische Chemie und Analytische Chemie, Johannes Gutenberg-Universität, Duesbergweg 10-14, D-55099 Mainz, Germany. ABSTRACT The interaction of N1-substituted uracils (cyclohexyl (1) and benzyl (2)) with three polymerisable recognition elements, the novel monomers 9-(3/4-vinylbenzyl)adenine (3) and 2,6-diamino-9-(3/4-vinylbenzyl)purine (4) and the previously synthesised monomer 2,6bis(acrylamido)pyridine (5), has been studied via 1H NMR in deuterio-chloroform solution. MIPs against (2) have been prepared using each of the monomers and tested in the chromatographic mode. The effect of the number and type of hydrogen bonds formed between the templates and the functional monomers is reflected in the values of the apparent association constants obtained from the solution study and by the performance of the subsequently prepared MIPs in the chromatographic mode. INTRODUCTION Interest in molecularly imprinted polymers (MIPs) has burgeoned in recent years [1]. The imprinting of nucleic acid bases and related compounds has attracted particular interest [2]. A survey of this literature shows that much MIP research has focused on the use of commercially available functional monomers, e.g. methacrylic acid, to create the binding sites in such noncovalent MIPs [3]. Among the exceptions is the use of 2,6-bis(acrylamido)pyridine (5) as a functional monomer for the imprinting of alloxan, where the selectivity of the MIP over the nonimprinted polymer (NIP) with respect to the recognition of thymine was also assessed [4]. Here, the ability of the monomer to form multiple hydrogen-bond interactions with substrate molecules was stressed. The same group has also recently reported the use of (5) as functional monomer in the imprinting of 5-fluorouracil [5]. We now wish to report the preparation of the novel monomers 9-(3/4-vinylbenzyl) adenine (3) and 2,6-diamino-9-(3/4-vinylbenzyl)purine (4) and their ability to form hydrogenbonded complexes with uracils. As a comparison, the previously reported functional monomer (5) has also been studied. Adenine is, of course, the base-pair partner of thymine in nucleic acids and so (3) could be expected to participate in hydrogen-bonding interactions with uracil molecules. The additional amino- function in (4) should lead to stronger association with uracils (1) and (2) by virtue of the potential extra hydrogen-bond interaction. The association of uracils with (5) has been studied to explore the difference between the amido- and aminofunctionalities.
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O R
N
NH2
NH O
(1) R = cyclohexyl (2) R = benzyl
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