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PubMed · 10076813

Novel chiral recognition elements for molecularly imprinted polymer preparation.

M Knutsson·H S Andersson·I A Nicholls
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Abstract

The use of a novel chiral functional monomer system in molecular imprinting protocols is described. The monomer, dibenzyl (2R,3R)-O-monoacryloyl tartrate, possesses a hydroxyl moiety which can be used to direct template-functional monomer interactions during molecular imprinting polymerization. This system simultaneously positions benzyl ester-protected carboxyl groups in close proximity to the template, which upon deprotection yield recognition sites with stronger ligand-binding capacities. Furthermore, the inherent chirality of the monomer engenders the polymer with an inbuilt preference for a given stereoisomer. Application of the system to the molecular imprinting of the cinchonidine alkaloids (+)-cinchonine and (-)-cinchonidine yielded stereoselective polymers. The effect of imprinting (+)-cinchonine produced a polymer which more than reversed the inherent chiral selectivity of the chiral monomer residues present in the matrix.

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Binding SitesCinchona AlkaloidsLigandsMolecular MimicryPolymersStereoisomerismJournal ArticleResearch Support, Non-U.S. Gov't

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BibTeXRIS

M Knutsson, H S Andersson, I A Nicholls. 1998. Novel chiral recognition elements for molecularly imprinted polymer preparation.. https://doi.org/10.1002/(sici)1099-1352(199812)11%3A1%2F6%3C87%3A%3Aaid-jmr396%3E3.0.co%3B2-a

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