Complete Enantiomer Separation by Chromatography on Potato Starch

Hess, Heinrich; Burger, Günther; Musso, Hans

doi:10.1002/anie.197806121

Cited by 34 publications

(11 citation statements)

References 9 publications

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“…Despite the first enantioseparation of an atropisomeric biphenyl on a polysaccharide matrix (potato starch) dates back to 1978 , polysaccharide‐based chiral stationary phases (CSPs) (Tables ) continue to be the most used supports for enantioseparation of atropisomers. The high versatility of polysaccharide‐based CSPs is due to their modular architecture where molecular, conformational, and supramolecular chirality cooperate to determine the enantioseparation outcome.…”

Section: Introductionmentioning

confidence: 99%

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

et al. 2017

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The term Atropisomerism defines a type of enantiomerism that arises from hindered rotation around an axis that makes two rotational isomers enantiomers. Atropisomeric compounds are present in nature, being important building blocks of many biologically active compounds. Atropisomers have been extensively studied in environmental and toxicological chemistry and, in particular, separating them has become a need in specific fields as organic synthesis and pharmaceutical research. High-performance LC has been fruitfully applied in this context, and despite HPLC separation on chiral stationary phase is considered as mature technology nowadays, in the last years several advancements and applications contributed to study compounds where axial chirality is of utmost importance. Moreover, dynamic chromatography has been exploited as a versatile tool for kinetic studies of systems with slow internal motion gaining essential information on their stereodynamic behavior. On this basis, current topics and trends in liquid-phase chromatography enantioseparation of atropisomers are presented herein with specific focus on new representative applications with HPLC, covering years 2010-2016. Some examples concerning supercritical fluid chromatography applications are also reported. This review aims to provide the reader with a modern overview of the field to highlight the renewed interest toward the chemistry of molecules with atropisomeric properties. A systematic compilation of all published literature has not been attempted.

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Section: Introductionmentioning

confidence: 99%

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

et al. 2017

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“…In particular, the immobilized version of these CSPs allowed expanding the range of solvents that can be used from the classic nhexane (n-hex), n-heptane, methanol (MeOH), ethanol (EtOH), isopropanol (IPA), acetonitrile (ACN), and water to mobile phases (MPs) containing nonstandard mid-polar solvents such as dichloromethane (DCM), methyl t-butyl ether (MTBE), tetrahydrofuran (THF), and ethyl acetate (EtOAc). The first reported enantioseparation on cellulose dates from 1951 14 and since the 1960s various derivatives of polysaccharides 15,16 were applied to enantioseparations, but with limited resolution ability. 17 Nevertheless, starting from the 1980s, several polysaccharide carbamates and benzoates were selected, optimized, and commercialized by means of an elegant work of molecular engineering.…”

Section: Polysaccharide-based Csps: a Brief Descriptionmentioning

confidence: 99%

Liquid Chromatography Enantioseparations of Halogenated Compounds on Polysaccharide‐Based Chiral Stationary Phases: Role of Halogen Substituents in Molecular Recognition

2015

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Halogenated chiral molecules have become important in several fields of science, industry, and society as drugs, natural compounds, agrochemicals, environmental pollutants, synthetic products, and chiral supports. Meanwhile, the perception of the halogen moiety in organic compounds and its role in recognition processes changed. Indeed, the recognition of the halogen bond as an intermolecular interaction occurring when the halogen acts as a Lewis acid had a strong impact, particularly in crystal engineering and medicinal chemistry. Due to this renewed interest in the potentialities of chiral organohalogens, here we focus on selected recent applications dealing with enantioseparations of halogenated compounds on polysaccharide-based chiral stationary phases (CSPs), widely used in liquid chromatography (LC). In particular, recently the first case of halogen bonding-driven high-performance LC (HPLC) enantioseparation was reported on a cellulose-based CSP. Along with enantioseparations performed under conventional HPLC, representative applications using supercritical fluid chromatography (SFC) are reported.

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“…Stewart and Doherty: Resolution of enantiomers using protein (bovine-serum albumin-agarose) as CSP [14] 1974 Blaschke: Resolution of chiral drugs using chiral polyacrylamide as CSP [15] 1975 Carm: Crown ether-based CSP [16] 1977 Frank: Resolution of amino acid derivatives by GC using L-valine t-butylamide polysiloxane (Chiralsil-Val) as CSP [17] 1978 Musso: Enantioseparation by chromatography on potato starch [18] 1978 Harada: Cyclodextrin-based CSP for LC [19] 1979 Pirkle: Resolution of enantiomers by chiral fluoro alcohol bonded (Pirkle-type) CSP in HPLC [20] 1980 Okamoto: One-handed helical poly(triphenylmethyl methacrylate) used as CSP for HPLC enantioseparation [21,22] 1984-1987 Okamoto: Cellulose and amylose tribenzoates and phenylcarbamates-based CSPs for HPLC [23][24][25] 1987 Juvancz: Permethylated β-cyclodextrin as CSP for GC [26] 1988 Schurig: Permethylated β-cyclodextrin diluted with polysiloxane as CSP for GC [27] (Continues)…”

Section: Introductionmentioning

confidence: 99%

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

Zhang

2021

J of Separation Science

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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.

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Complete Enantiomer Separation by Chromatography on Potato Starch

Abstract: SS bond distances in S 7 0 2 can be derived using the wave numbers given in Table 1. On the basis of these values, and observations made in structural studies on S80[8a1 and S7018b1, we suggest the following structure for S 7 0 2 (bond lengths in pm): 206 219

Cited by 34 publications

References 9 publications

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

Liquid Chromatography Enantioseparations of Halogenated Compounds on Polysaccharide‐Based Chiral Stationary Phases: Role of Halogen Substituents in Molecular Recognition

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

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