High-Performance Liquid Chromatographic Enantioseparation of Racemic Drugs Based on Homochiral Metal–Organic Framework

Abstract

Homochiral metal-organic frameworks with fine-tuned pore sizes/walls and large surface areas are promising porous materials for enantioseparation considering the traditional zeolite molecular sieves have no chirality. Using enantiopure pyridyl-functionalized salen [(N-(4-Pyridylmethyl)-L-leucine·HBr)] as a starting material, we have prepared a noninterpenetrated three-dimensional homochiral metal organic framework {[ZnLBr]·H2O}n, which was further used as a chiral stationary phase for high-performance liquid chromatography to enantioseparate racemic drugs, showing excellent performances in enantioseparation of drugs. The metal-organic framework can be regarded as a novel molecular sieve-like material with a chiral separation function based on the relative sizes of the chiral channels and the resolved molecules.

Biologically derived metal organic frameworks

“…[228] A flexible cerium tetradentate carboxylate MOF with restructuring driven by guest molecules, displaying molecular-level recognition for p-and mxylenes giving high selectivities, thereby adding to the increasing number of flexible MOFs that can be used for separations. [35,223,229] Stoddart et al recently reported a high selectivity of CD-MOFs (γ-CD) (see section 3.4), which exhibited high shape selectivity, for separation of aromatic hydrocarbons using alkali metal cations. [215] The retention order of o-> m-> p-xylene separation was determined through adsorption isotherms and liquid-phase chromatographic measurements, with impressive regioselectivity of ethyltoluene and cymene regioisomers during the liquid-phase chromatography.…”

Application of Metal-Organic Frameworks in Chromatographic Separation

“…但 R-MOF-silica 却对(R)-异构体的吸附能 力强, 对未取代的、对位取代的苯甲亚砜的分离因子要 大于邻位、间位取代的苯甲亚砜, 并且, 对亚砜中硫原 子直接连接苯基的物质的分离度更高 [77] . [83] . 不 同 于 …”

Preparation and Enantioseparation of Biselector Chiral Stationary Phases Based on Amylose and Chitin Derivatives

“…[1][2][3][4] In general, one enantiomer exhibits desirable therapeutic activity, while another one may exhibit less effects, antagonistic action, or even toxic effects. High-performance liquid chromatography (HPLC) based on chiral stationary phases (CSPs) has been one of the most common and efficient techniques for enantioseparation and the preparation of optical isomers.…”