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Novel chiral recognition elements for molecularly imprinted polymer preparation
Author(s) -
Knutsson Malin,
Andersson Håkan S.,
Nicholls Ian A.
Publication year - 1998
Publication title -
journal of molecular recognition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.401
H-Index - 79
eISSN - 1099-1352
pISSN - 0952-3499
DOI - 10.1002/(sici)1099-1352(199812)11:1/6<87::aid-jmr396>3.0.co;2-a
Subject(s) - molecularly imprinted polymer , molecular imprinting , molecular recognition , polymer , chemistry , combinatorial chemistry , nanotechnology , materials science , organic chemistry , selectivity , catalysis , molecule
The use of a novel chiral functional monomer system in molecular imprinting protocols is described. The monomer, dibenzyl (2 R ,3 R )‐ 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. Copyright © 1998 John Wiley & Sons, Ltd.