Liquid-liquid chromatography in enantioseparations

Tong, Shengqiang

doi:10.1016/j.chroma.2020.461345

Cited by 13 publications

(4 citation statements)

References 73 publications

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“…Furthermore, HSCCC chiral separation technology boasts a notable sample loading capacity and holds considerable industrial promise for chiral separation. This capability enables the cost‐effective production of numerous pure enantiomeric compounds from racemic mixtures, positioning it as an invaluable tool in the field of enantiomeric preparative separation [17].…”

Section: Introductionmentioning

confidence: 99%

Continuous chiral separation process for high‐speed countercurrent chromatography established and scaled up: A case of Voriconazole enantioseparation

Sun,

Huang,

Pei

et al. 2024

J of Separation Science

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An efficient method for the continuous separation of Voriconazole enantiomers was developed using sulfobutyl ether‐β‐cyclodextrin (SBE‐β‐CD) as a chiral selector in high‐speed countercurrent chromatography (HSCCC) with different types. The separation was performed using a two‐phase solvent system consisting of n‐hexane/ethyl acetate/100 mmol/L phosphate buffer solution (pH = 3.0, containing 50 mmol/L SBE‐β‐CD) (1.5:0.5:2, v/v/v). A fast and predictable scale‐up process was achieved using an analytical DE HSCCC instrument. The optimized parameters were subsequently applied to a preparative Tauto HSCCC instrument, resulting in consistent separation time and enantiomeric purity, with throughput boosted by a remarkable 11‐fold. Preparative HSCCC successfully separated 506 mg of the racemate, delivering enantiomers exceeding 99% purity as confirmed by high‐performance liquid chromatography analysis. This investigation presents an effective methodology for forecasting the HSCCC scale‐up process and attaining continuous separation of chiral drugs.

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Section: Introductionmentioning

confidence: 99%

Continuous chiral separation process for high‐speed countercurrent chromatography established and scaled up: A case of Voriconazole enantioseparation

Sun,

Huang,

Pei

et al. 2024

J of Separation Science

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“…9 Thus, it is inapplicable to aliphatic AAs, which usually demonstrate rather weak optical activity. Other strategies principally rely on host−guest interactions to discriminate molecular chirality by preferentially interacting with one enantiomer over the other one, where specifically designed chiral sensors are essential to translate the chiral information of the chiral molecules by coupling with electrochemistry, 10 chromatography, 11 and spectroscopy methods. 12 As can be seen, most of them require complicated instrumentation and procedures or lack satisfactory sensitivity for diverse chiral targets.…”

Section: Introductionmentioning

confidence: 99%

Quinine-Fabricated Surface-Enhanced Raman Spectroscopy Chiral Sensing Platform Enables Simultaneous Enantioselective Discrimination and Identification of Aliphatic Amino Acids

et al. 2023

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Due to low optical activity and structural simplicity, synchronous chiral discrimination and identification of aliphatic amino acids (AAs) are still challenging yet demanding. Herein, we developed a novel surface-enhanced Raman spectroscopy (SERS)-based chiral discrimination-sensing platform for aliphatic AAs, in which l- and d-enantiomers are able to discriminately bind with quinine to generate distinct differences in the SERS vibrational modes. Meanwhile, the plasmonic sub-nanometer gaps supported by the rigid quinine enable the maximization of SERS signal enhancement to reveal feeble signals, allowing for simultaneously acquiring the structural specificity and enantioselectivity of aliphatic amino acid enantiomers in a single SERS spectrum. Different kinds of chiral aliphatic AAs were successfully identified by using this sensing platform, demonstrating its potential and practicality in recognizing chiral aliphatic molecules.

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“…Liquid chromatography (LC) using chiral stationary phases (CSPs) is known to be extremely convenient, accurate, versatile, and widely used technique in diverse fields of applications. [1][2][3][4] By choosing a known μ-opioid receptor agonist 5 tetrapeptide Tyr-Arg-Phe-Lys-NH 2 (1; Figure 1), we have previously observed that CSPs, based on R and S-(3, 3 0 -diphenyl-1, 1 0 -binaphthyl)-20-crown-6 chiral selectors (commercially available as CROWNPAK CR-I (+) or (À); Figure 1), are optimal for tetrapeptide 1 chiral separations. 6 It was later found out that these stationary phases also work surprisingly well in other structurally similar tetrapeptide enantioseparations.…”

Section: Introductionmentioning

confidence: 99%

Chiral recognition mechanism studies of Tyr‐Arg‐Phe‐Lys‐NH₂ tetrapeptide on crown ether‐based chiral stationary phase

Upmanis,

Sevostjanovs,

Kažoka

2023

Chirality

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Even though chiral recognition for crown‐ether CSPs is generally understood, on a molecular level, exact mechanisms for the resolution are still unclear. Furthermore, short peptide analytes often contain multiple amino moieties capable of binding to the crown ether selector. In order to extend the understanding in chiral recognition mechanisms, polar organic mode separation of Tyr‐Arg‐Phe‐Lys‐NH2 tetrapeptide llll/dddd enantiomers on S‐ and R‐(3,3′‐diphenyl‐1,1′‐binaphthyl)‐20‐crown‐6 stationary phases was studied with 50‐mM perchloric acid in methanol as mobile phase. Deviation from the generally acceptable 1:1 stoichiometry was supported by mass spectroscopy analysis of the formed complexes between tetrapeptide enantiomer and crown ether selectors, which revealed adducts possessing 1:1, 1:2, and 1:3 stoichiometry. Further investigation of complexation induced shifts by NMR indicated on different binding mechanisms between llll/dddd enantiomers of Tyr‐Arg‐Phe‐Lys‐NH2 and crown ether selectors. Enantioselective proton shifts were observed in studied tetrapeptide tyrosine and phenylalanine residues exclusively for llll enantiomer upon binding with S‐(3,3′‐diphenyl‐1,1′‐binaphthyl)‐20‐crown‐6 selector (and dddd enantiomer with R‐(3,3′‐diphenyl‐1,1′‐binaphthyl)‐20‐crown‐6 selector), indicating that these two amino acid residues contribute to chiral recognition. The obtained results were in agreement with the LC data.

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Liquid-liquid chromatography in enantioseparations

Cited by 13 publications

References 73 publications

Continuous chiral separation process for high‐speed countercurrent chromatography established and scaled up: A case of Voriconazole enantioseparation

Continuous chiral separation process for high‐speed countercurrent chromatography established and scaled up: A case of Voriconazole enantioseparation

Quinine-Fabricated Surface-Enhanced Raman Spectroscopy Chiral Sensing Platform Enables Simultaneous Enantioselective Discrimination and Identification of Aliphatic Amino Acids

Chiral recognition mechanism studies of Tyr‐Arg‐Phe‐Lys‐NH₂ tetrapeptide on crown ether‐based chiral stationary phase

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Liquid-liquid chromatography in enantioseparations

Cited by 13 publications

References 73 publications

Continuous chiral separation process for high‐speed countercurrent chromatography established and scaled up: A case of Voriconazole enantioseparation

Continuous chiral separation process for high‐speed countercurrent chromatography established and scaled up: A case of Voriconazole enantioseparation

Quinine-Fabricated Surface-Enhanced Raman Spectroscopy Chiral Sensing Platform Enables Simultaneous Enantioselective Discrimination and Identification of Aliphatic Amino Acids

Chiral recognition mechanism studies of Tyr‐Arg‐Phe‐Lys‐NH2 tetrapeptide on crown ether‐based chiral stationary phase

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Chiral recognition mechanism studies of Tyr‐Arg‐Phe‐Lys‐NH₂ tetrapeptide on crown ether‐based chiral stationary phase