Chiral Separations: A Review of Current Topics and Trends

Ward, Timothy J.; Ward, Karen D.

doi:10.1021/ac202892w

Cited by 430 publications

(292 citation statements)

References 119 publications

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“…Enantiomers remain a challenge to be separated owing to their identical physical and chemical properties in an achiral environment 3 . For decades, extensive research has been devoted to the development of chiral separation processes 3,4 . Resolution methods, with an emphasis on chromatographic separation and preferential crystallization, have been reported.…”

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confidence: 99%

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

et al. 2014

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The separation of racemic molecules is of substantial significance not only for basic science but also for technical applications, such as fine chemicals and drug development. Here we report two isostructural chiral metal-organic frameworks decorated with chiral dihydroxy or -methoxy auxiliares from enantiopure tetracarboxylate-bridging ligands of 1,1 0 -biphenol and a manganese carboxylate chain. The framework bearing dihydroxy groups functions as a solid-state host capable of adsorbing and separating mixtures of a range of chiral aromatic and aliphatic amines, with high enantioselectivity. The host material can be readily recycled and reused without any apparent loss of performance. The utility of the present adsorption separation is demonstrated in the large-scale resolution of racemic 1-phenylethylamine. Control experiments and molecular simulations suggest that the chiral recognition and separation are attributed to the different orientations and specific binding energies of the enantiomers in the microenvironment of the framework.

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confidence: 99%

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

et al. 2014

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“…S ince the first demonstration of the handedness of tartaric acid molecules by Pasteur 1 , resolution of enantiomers and dissymmetric induction in synthesis have been important from the perspectives of both science and technology [2][3][4][5] . In recent years, much effort has been expended on researching methods of fabricating nanoscale chiral surfaces, in many cases with the goal of improving enantioselectivity in asymmetric induction 6 , high-performance liquid chromatography 7,8 and high-sensitivity chirality detection 9,10 .…”

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confidence: 99%

Diastereomeric liquid crystal domains at the mesoscale

et al. 2015

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In many technologies used to achieve separation of enantiomers, chiral selectors are designed to display differential affinity for the two enantiomers of a chiral compound. Such complexes are diastereomeric, differing in structure and free energy for the two enantiomers and enabling chiral discrimination. Here we present evidence for strong diastereomeric interaction effects at the mesoscale, manifested in chiral liquid crystal guest materials confined in a chiral, nanoporous network of semi-crystalline helical nanofilaments. The nanoporous host is itself an assembly of achiral, bent-core liquid crystal molecules that phase-separate into a conglomerate of 100 micron-scale, helical nanofilament domains that differ in structure only in the handedness of their homogeneous chirality. With the inclusion of a homochiral guest liquid crystal, these enantiomeric domains become diastereomeric, exhibiting unexpected and markedly different mesoscale structures and orientation transitions producing optical effects in which chirality has a dominant role.

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“…In an achiral environment, enantiomers have identical properties except for their chiroptics (polarimetry, circular dichroism (CD) and optical rotatory dispersion (ORD)). The stereogenic unit is frequently generated by a tetrahedron carbon include liquid chromatography (LC) [42], GC [43,44], capillary electrophoresis (CE), supercritical fluid chromatography (SFC), among others [45][46][47]. Among these technologies, chromatography has been the most used technique for the analysis of chiral pollutants, by two different approaches: direct and indirect methods [48,49].…”

Section: Basic Concepts Of Chiralitymentioning

confidence: 99%

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

Ribeiro

Maia

et al. 2017

Symmetry

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Abstract:In recent decades, the presence of micropollutants in the environment has been extensively studied due to their high frequency of occurrence, persistence and possible adverse effects to exposed organisms. Concerning chiral micropollutants in the environment, enantiomers are frequently ignored and enantiomeric composition often neglected. However, enantioselective toxicity is well recognized, highlighting the need to include enantioselectivity in environmental risk assessment. Additionally, the information about enantiomeric fraction (EF) is crucial since it gives insights about: (i) environmental fate (i.e., occurrence, distribution, removal processes and (bio)degradation); (ii) illicit discharges; (iii) consumption pattern (e.g., illicit drugs, pharmaceuticals used as recreational drugs, illicit use of pesticides); and (iv) enantioselective toxicological effects. Thus, the purpose of this paper is to provide a comprehensive review about the enantioselective occurrence of chiral bioactive compounds in aquatic environmental matrices. These include pharmaceuticals, illicit drugs, pesticides, polychlorinated biphenyls (PCBs) and polycyclic musks (PCMs). Most frequently analytical methods used for separation of enantiomers were liquid chromatography and gas chromatography methodologies using both indirect (enantiomerically pure derivatizing reagents) and direct methods (chiral stationary phases). The occurrence of these chiral micropollutants in the environment is reviewed and future challenges are outlined.

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Chiral Separations: A Review of Current Topics and Trends

Cited by 430 publications

References 119 publications

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

Diastereomeric liquid crystal domains at the mesoscale

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

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