用于手性药物筛分的手性功能化膜

Chiral-functionalized membranes for chiral drugs sieving

何思佳 ¹张雅倩 ¹Sravan Baddi ¹赵常利 ¹窦晓秋 ¹冯传良¹

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作者信息

1. State Key Lab of Metal Matrix Composites,School of Materials Science and Engineering,Shanghai Jiao Tong University,Shanghai 200240,China
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摘要

将手性整合到薄膜体系中为手性分离技术的发展提供了独特的方向.然而,在膜层之间创建手性位点仍是一个有待解决的问题.在此,我们制作了一种壳聚糖/氧化石墨烯(CG)基薄膜,通过与L-色氨酸衍生物(LPWM)的非共价相互作用,CG-LPWM薄膜不仅保持优异的机械强度,同时具有手性功能.LPWM在薄膜中引入了手性环境,使得薄膜不仅能够视觉识别手性分子,而且对手性药物具有一定的分离性能:伪麻黄碱的光学异构体过量值超过80％.手性识别源于手性组装体与其中一种异构体具有更强或更多的氢键作用导致的优先结合.这项工作通过简单的非共价相互作用制作了手性薄膜,为手性修饰的层状膜实现对映体识别与分离指引了方向.

Abstract

Current trend that integrates chiral designs into robust membrane systems is providing distinct horizons for the development of chiral separation technology.However,creating chiral sites in-between membrane laminates is still an open issue.Herein,we demonstrate a decorated layered chit-osan/graphene oxide(CG)membrane via non-covalent inter-actions with L-tryptophan derivatives(LPWM),yielding materials with chiral functionality and superior mechanical strength.LPWM introduces chiral environment into the membrane,giving rise to visual recognition sensitivity and decent enantioseparation performance toward chiral drug molecules,with optical isomeric excess value exceeding 80％for pseudoephedrine(PEP).The chiral discrimination is as-sociated with preferential binding of one of the isomers due to stronger or additional H-bonds with chiral assemblies.This work not only paves a new way for the fabrication of chiral membranes via a simple non-covalent interaction,but also guides a potential direction to realize enantioseparation em-ploying decorated laminated membranes.

关键词

supramolecular chirality/self-assembly/chiral dis-crimination/decorated membranes

Key words

supramolecular chirality/self-assembly/chiral dis-crimination/decorated membranes

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基金项目

Leading Talents in Science and Technology Innovation under the National Ten Thousand Talents Plan,the National Natural Scien(51833006)

Leading Talents in Science and Technology Innovation under the National Ten Thousand Talents Plan,the National Natural Scien(52003154)

Innovation Program of Shanghai Municipal Education Commission(201701070002E00061)

Science and Technology Commission of Shanghai Municipality(19441903000)

Science and Technology Commission of Shanghai Municipality(19ZR1425400)

Shanghai Jiao Tong University(SJTU)Transmed Awards Research(WF540162603)

Shanghai Pujiang Program(20PJ1407400)

Natural Science Foundation of Shanghai(20ZR1425500)

出版年

2024

中国科学:材料科学(英文)

CSTPCD

ISSN：

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