Recent developments in preparative-scale supercritical fluid- and liquid chromatography for chiral separations

Speybrouck, David; Howsam, Michael; Lipka, Emmanuelle

doi:10.1016/j.trac.2020.116090

Cited by 34 publications

(26 citation statements)

References 87 publications

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“…These include separation of enantiomers in various techniques such as GC, , HPLC, , SFC, capillary electrophoresis (CE), ,, capillary electrochromatography (CEC), and microchip-based platforms . Another set of review papers deal with specific types of CSs, such as polysaccharide derivatives, , glycopeptide antiobiotics, − CDs, − Pirkle-type, chiral ion-exchangers, and MOFs. ,, One more group of review papers deals with high-resolution and fast separations, , chiral recognition mechanisms, ,,− and molecular modelling. − ,,− There are also review papers published on various aspects of application of enantioseparations, in particular about preparative and product scale separations, − enantioselective pharmaceutical, − biomedical, ,− environmental, , and food and beverage analysis . The narrative thread of all the above-mentioned methods, techniques, and applications is that they are all based on the enantioselective noncovalent interaction between two counterparts, of which one is called analyte, selectand, guest, or ligand and the other is called the selector, host, or receptor.…”

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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“…310 The advantages and applications of supercritical fluid chromatography for enantioseparation are described in the following reviews. [311][312][313][314][315][316][317][318][319][320] When merging simulated moving bed with supercritical fluid chromatography technologies it leads to a purification procedure with unique characteristics with advantages of both techniques, named Supercritical fluid simulated moving bed (SFC-SMB). In 1996, Clavier et al 321 described for the first time the fusion between the two chromatography methods.…”

Section: Supercritical Fluid Simulated Moving Bedmentioning

confidence: 99%

“…310 The advantages and applications of supercritical fluid chromatography for enantioseparation are described in the following reviews. 311–320…”

Section: Continuous Chromatographymentioning

confidence: 99%

Semi-continuous and continuous processes for enantiomeric separation

2022

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“…SFC technique is increasingly used in the pharmaceutical industry for drug analysis, development and purification [ 18 ]. SFC is a particularly widespread technique for determining the enantiomeric purity of chiral compounds, but also for separating enantiomers on a preparative scale [ 19 , 20 , 21 , 22 , 23 ]. The exigency of preparative scale SFC protocols for enantiopure compounds is rising from its comparative advantages compared to HPLC such that the following are present: (a) faster flow-rate and column equilibration due to lower viscosity; (b) higher column loadability, hence productivity, is better than HPLC; (c) solubility in supercritical fluid decreases rapidly as the pressure decreases near the critical point, facilitating recovery of the isomer fractions and increasing yield; (d) instrumentation allows stacked or overlapped injections improving productivity and reducing solvent consumption; (e) mobile phase is mainly constituted of carbon dioxide, which is non-flammable, less expensive and less toxic than common organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides

Buljan

Roje

2022

Marine Drugs

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Enantioseparation of the newly synthesized series of novel quinoline-2(1H)-one epoxide structures rac-6a–c and rac-8a–c, named marinoepoxides, is described. Marinoepoxide rac-6a, the key intermediate in the total synthesis of natural products marinoaziridines A and B, as well as their structural analogues, was synthesized by addition of the achiral ylide generated in situ from the sulfonium salt 5 or 7, to the carbon-oxygen double bond of the corresponding quinoline-2(1H)-one-4-carbaldehyde 4a–c in good yield. Separation of enantiomers of (±)-2,3,3-trisubstituted marinoepoxides rac-6a–c and (±)-trans-2,3-disubstituted marinoepoxides rac-8a–c was studied using two immobilized polysaccharide type chiral stationary phases (CSPs); tris-(3,5-dichlorophenylcarbamoyl)cellulose stationary phase (CHIRAL ART Cellulose-SC) and tris-(3,5-dimethylphenylcarbamoyl)amylose stationary phase (CHIRAL ART Amylose-SA). Enantioseparation conditions were explored by high-performance liquid chromatography (HPLC) using dimethyl carbonate/alcohol mixtures and n-hexane/ethanol (80/20, v/v) as mobile phase, and by supercritical fluid chromatography (SFC) using CO2/alcohol mixtures as mobile phase. In all examined racemates, enantioseparation was successfully achieved, but its efficiency largely depended on the structure of chiral selector and type/composition of the mobile phase.

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Recent developments in preparative-scale supercritical fluid- and liquid chromatography for chiral separations

Cited by 34 publications

References 87 publications

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Semi-continuous and continuous processes for enantiomeric separation

Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides

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