Knutsson M, Andersson H S, Nicholls I A
Bioorganic Chemistry Laboratory, University of Kalmar, Sweden.
J Mol Recognit. 1998 Winter;11(1-6):87-90. doi: 10.1002/(SICI)1099-1352(199812)11:1/6<87::AID-JMR396>3.0.CO;2-A.
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.
本文描述了一种新型手性功能单体体系在分子印迹方案中的应用。该单体，二苄基(2R,3R)-O-单丙烯酰酒石酸酯，具有一个羟基部分，可用于在分子印迹聚合过程中指导模板-功能单体相互作用。该体系同时将苄基酯保护的羧基定位在靠近模板的位置，脱保护后可产生具有更强配体结合能力的识别位点。此外，单体固有的手性使聚合物对给定的立体异构体具有内在偏好。将该体系应用于金鸡纳生物碱(+)-辛可宁和(-)-辛可尼定的分子印迹，得到了立体选择性聚合物。印迹(+)-辛可宁的效果产生了一种聚合物，该聚合物几乎逆转了基质中存在的手性单体残基固有的手性选择性。
