Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

Abstract

Separations and analyses of chiral compounds are important in many fields, including pharmaceutical production, preparation of chemical intermediates, and biochemistry. High-performance liquid chromatography using a chiral stationary phase is regarded as one of the most valuable methods for enantiomeric separation and analysis because it is highly efficient, is broadly applicable, and has powerful separation capability. The focus for development of this method is the identification of novel chiral stationary phases with superior recognition performance and good stability. The present article reviews recent progress in the development of new chiral stationary phases for high-performance liquid chromatography between January 2018 and June 2021. These newly reported chiral stationary phases are divided into three categories: small organic moleculebased (cyclodextrin and its derivatives, macrocyclic antibiotics, cinchona alkaloids, and other low molecular weight chiral molecules), macromoleculebased (cellulose and amylose derivatives, chitin and chitosan derivatives, and synthetic helical polymers) and chiral porous material-based (chiral metal-organic frameworks, chiral covalent organic frameworks, and chiral inorganic mesoporous silicas). Each type of chiral stationary phase is discussed in detail.

Solvent‐dependent helix inversion in optically active poly(diphenylacetylene)s and their chiral recognition abilities as chiral stationary phases for high‐performance liquid chromatography

“…In 1980, Okamoto et al reported that the single‐handed helical poly(triphenylmethyl methacrylate) obtained by the helix‐sense‐selective anionic polymerization of triphenylmethyl methacrylate showed excellent chiral recognition abilities toward various racemic compounds when used as a CSP for HPLC 7–9 . Since then, a large variety of CSPs based on helical polymers with a preferred‐handed helical structures have been developed, some of which are commercially available 10–16 …”

Enantioseparation of basic drugs by reverse phase high‐performance liquid chromatography system using carboxymethyl‐β‐cyclodextrin as chiral mobile phase additive

“…In the chiral HPLC, enantioseparation can be accomplished directly with a chiral stationary phase (CSP) and chiral mobile phase additive (CMPA) 5–10 . In recent years, more and more researchers have developed and used chiral columns, but they are of high price, poor stability, and have a comparatively short lifetime 11 . Moreover, because of its strong stereospecificity, the chiral HPLC column cannot be utilized widely 11,12 .…”

“…[5][6][7][8][9][10] In recent years, more and more researchers have developed and used chiral columns, but they are of high price, poor stability, and have a comparatively short lifetime. 11 Moreover, because of its strong stereospecificity, the chiral HPLC column cannot be utilized widely. 11,12 On the other hand, the method of utilizing the CMPA has been widely used in exploratory research as a versatile and flexible method to demonstrate greater potential in chiral separation.…”

“…11 Moreover, because of its strong stereospecificity, the chiral HPLC column cannot be utilized widely. 11,12 On the other hand, the method of utilizing the CMPA has been widely used in exploratory research as a versatile and flexible method to demonstrate greater potential in chiral separation. 13,14 So far, a wide range of chiral selectors, including cyclodextrins (CDs), [14][15][16][17][18] chiral ion-pair inclusions, 19,20 and chiral ligand-exchange inclusions, [21][22][23] have been explored in CMPA techniques.…”

In‐situ grown metal organic framework synergistic system for the enantioseparation of three drugs in open tubular capillary electrochromatography

“…Homochiral MOFs, due to their chiral properties and disposition, including enantiopure ligands or special helical topology architectures, are one of the host materials for the appropriate enantioselective separation of racemic drugs in the chemical and pharmaceutical industries [15][16][17]. Homochiral MOFs have attracted increasing attention to racemic drugs enantioseparation as chiral stationary phases (CSP) for HPLC [2,15,18], GC [19][20][21], and CEC [17,22] in recent years. Biologically derived ligands have proved successful in the synthesis of MOFs, such as dipeptides [23], tripeptides [24], nucleobases [25], and their derivatives [2,15], but the application of these homochiral MOFs in CEC for enantioseparation has been rarely reported.…”