State-of-the-art and recent developments of immobilized polysaccharide-based chiral stationary phases for enantioseparations by high-performance liquid chromatography (2013–2017)

Padró, Juan M.; Keunchkarian, Sonia

doi:10.1016/j.microc.2018.04.017

Cited by 75 publications

(38 citation statements)

References 159 publications

(209 reference statements)

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“…7 Therefore, the development of novel immobilized chiral stationary phases (CSPs) has always been an important research topic in the field of chromatography. [8][9][10] At the same time, the preparation of multifunctional immobilized CSPs with high separation efficiency and wide applicability is also an important research content in current chiral resolution chromatography technology. Recently, HPLC multifunctional immobilized CSPs have been successfully developed.…”

Section: Introductionmentioning

confidence: 99%

Preparation and chromatographic performance of a multifunctional immobilized chiral stationary phase based on dialdehyde microcrystalline cellulose derivatives

Gao

Chen

et al. 2019

Chirality

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A novel high‐performance liquid chromatography (HPLC) multifunctional immobilized chiral stationary phase was prepared by bonding dialdehyde microcrystalline cellulose to aminosilica via Schiff base reaction and then derivatized with 3,5‐dimethylphenyl isocyanate. The HPLC multifunctional immobilized chiral stationary phase could not only achieve chiral separation but also achieve achiral separation. Chiral separation evaluation showed that 1‐(1‐naphthyl)ethanol and mandelonitrile got separation in normal phase (NP) mode. Ranolazine, benzoin ethyl ether, metalaxyl, and diclofop were successfully separated in reversed phase (RP) mode. Aromatic compounds such as polycyclic aromatic hydrocarbons (PAHs), anilines, and aromatic acids were selected as analytes to investigate the achiral separation performance of the multifunctional immobilized chiral stationary phase in NP and RP modes. The achiral separation evaluation showed that six PAHs could get good separation within 10 minutes in NP mode. Four aromatic acids were well separated in RP mode. The retention mechanism of aromatic compounds on the stationary phase was discussed, founding that π‐π interaction, π‐π electron‐donor‐acceptor (EDA) interaction, and hydrogen bonding interaction played important roles during the achiral separation process. This multifunctional immobilized chiral stationary phase had the advantages of simple bonding steps, short reaction time, and no need for space arm.

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Section: Introductionmentioning

confidence: 99%

Preparation and chromatographic performance of a multifunctional immobilized chiral stationary phase based on dialdehyde microcrystalline cellulose derivatives

Gao

Chen

et al. 2019

Chirality

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show abstract

“…Despite the solvent limitation in mobile phase composition, the polysaccharide-based CSPs are compatible with normal, reversed, polar organic and polar ionic elution modes. Moreover, immobilized polysaccharides emerged as a reliable alternative allowing the use of a broader selection of solvents as mobile phases [53].…”

Section: Liquid Chromatographymentioning

confidence: 99%

Chiral Separations in Preparative Scale: A Medicinal Chemistry Point of View

2020

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Enantiomeric separation is a key step in the development of a new chiral drug. Preparative liquid chromatography (LC) continues to be the technique of choice either during the drug discovery process, to achieve a few milligrams, or to a scale-up during the clinical trial, needing kilograms of material. However, in the last few years, instrumental and technical developments allowed an exponential increase of preparative enantioseparation using other techniques. Besides LC, supercritical fluid chromatography (SFC) and counter-current chromatography (CCC) have aroused interest for preparative chiral separation. This overview will highlight the importance to scale-up chiral separations in Medicinal Chemistry, especially in the early stages of the pipeline of drugs discovery and development. Few examples within different methodologies will be selected, emphasizing the trends in chiral preparative separation. The advantages and drawbacks will be critically discussed.

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“…In recent years, HPLC has become a versatile and selective tool for the separation of chiral compounds, in which CSPs play a key role. Because of their abundance in nature and special structural features, polysaccharide‐based CSPs have always attracted considerable attention [10–14]. In particular, the chemically modified amylose‐ and cellulose‐based CSPs developed by Okamoto and co‐workers have shown remarkable enantioselectivity for a majority of racemates [15,16].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric analysis of simendan on polysaccharide‐based stationary phases by polar organic solvent chromatography

Cheng

Cai

et al. 2020

J of Separation Science

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Herein, the enantiomeric separation of simendan by high-performance liquid chromatography with ultraviolet detection using polysaccharide-based chiral stationary phases in polar organic mode is described. Three chiral columns (Chiralpak AD-H, Chiralcel OD-H, and Chiralpak AS) were screened using pure methanol and acetonitrile without additives under isocratic conditions. A reversed elution order was observed on the Chiralpak AD-H column when the methanol content in the mobile phase (methanol-acetonitrile mixtures) was above 10%, whereby levosimendan eluted prior to dextrosimendan. Further, it was found that increasing temperature effectively improved the enantioresolution on the Chiralpak AD-H column. Van't Hoff analysis was performed to evaluate the contribution of enthalpy and entropy to the chiral discrimination process. The best enantioseparation (α = 3.00, Rs = 12.85) was obtained on the Chiralpak AD-H column with methanol as the mobile phase at 40 • C. Thus, a quantitative method for the resolution of dextrosimendan was established and validated, which could be used as a reference for the determination of dextrosimendan in levosimendan products. K E Y W O R D Schiral stationary phases, enantiomeric separation, polar organic solvent chromatography, quantitative analysis, simendan Enantiomeric analysis of simendan on polysaccharidebased stationary phases by polar organic solvent chromatography.

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State-of-the-art and recent developments of immobilized polysaccharide-based chiral stationary phases for enantioseparations by high-performance liquid chromatography (2013–2017)

Cited by 75 publications

References 159 publications

Preparation and chromatographic performance of a multifunctional immobilized chiral stationary phase based on dialdehyde microcrystalline cellulose derivatives

Preparation and chromatographic performance of a multifunctional immobilized chiral stationary phase based on dialdehyde microcrystalline cellulose derivatives

Chiral Separations in Preparative Scale: A Medicinal Chemistry Point of View

Enantiomeric analysis of simendan on polysaccharide‐based stationary phases by polar organic solvent chromatography

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