Novel chiral recognition elements for molecularly imprinted polymer preparation

✍ Scribed by Malin Knutsson; Håkan S. Andersson; Ian A. Nicholls

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 59 KB
• Volume: 11
• Category: Article
• ISSN: 0952-3499
• DOI: 10.1002/(sici)1099-1352(199812)11:1/6<87::aid-jmr396>3.0.co;2-a

✦ Synopsis

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 (À)-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.