Effective methodologies for enantiomeric separations of 150 pharmacology and toxicology related 1°, 2°, and 3° amines with core-shell chiral stationary phases

Hellinghausen, Garrett; Roy, Daipayan; Lee, Jauh T.; Wang, Yadi; Weatherly, Choyce A.; Lopez, Diego A.; Nguyen, Kate A.; Armstrong, J. D.; Armstrong, Daniel W.

doi:10.1016/j.jpba.2018.03.032

Cited by 42 publications

(24 citation statements)

References 26 publications

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“…Preliminary screening with all four CSPs using 50 chiral compounds in each compatible chromatographic mode (PIM, POM, RP, and NP) was performed, making 200 analyses per CSP. When a partial separation of the enantiomers was obtained, this separation could be significantly improved by modulating the mobile phase as shown in previous studies, but it should be noted that this was not the aim of this study . The best screening result (in terms of R s ) by each CSP are tabulated according to each compound in Table .…”

Section: Resultsmentioning

confidence: 87%

“…Of these, vancomycin, teicoplanin, and ristocetin A were commercialized as the CHIROBIOTICs as well as teicoplanin's aglycone . Since the recent development of superficially porous particles or core‐shell particles, which offer high throughput and more effective separations, several studies have been explored using core‐shell macrocyclic glycopeptide‐based CSPs (TeicoShell [TS] and VancoShell [VS]) . This has been particularly useful to ultrafast chiral separations needed in second dimension (2D) LC .…”

Section: Introductionmentioning

confidence: 99%

“…Comprehensive studies have indicated that vancomycin is most useful for the separation of basic amines, while teicoplanin is most useful for the separation of acids, specifically amino acids . When exploring the structural interactions driving these separations, it is difficult to assess their separation mechanisms due to the diverse and complex interactions of each macrocyclic glycopeptide .…”

Section: Introductionmentioning

confidence: 99%

“…Recently, a modified macrocyclic glycopeptide‐based CSP, NicoShell (NS), was used for the novel LC enantiomeric separation of nicotine from tobacco e‐liquids and several nicotine‐related compounds, including carcinogenic tobacco‐specific nitrosamines . NicoShell was further utilized for the separation of several chiral amines . An effective methodology was proposed for core‐shell CSPs and was used in this study to evaluate a new selector, the vancomycin Edman degradation product (EDP) .…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of the Edman degradation product of vancomycin bonded to core‐shell particles as a new HPLC chiral stationary phase

et al. 2018

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A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3 minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

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Section: Resultsmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Evaluation of the Edman degradation product of vancomycin bonded to core‐shell particles as a new HPLC chiral stationary phase

et al. 2018

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“…(see Table ). Also, VancoShell is known to be effective for the separation of a variety of amines . VancoShell separated five different amines in this study (see Table ).…”

Section: Resultsmentioning

confidence: 93%

Enantiomeric impurities in chiral catalysts, auxiliaries, and synthons used in enantioselective syntheses. Part 5

et al. 2019

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The enantiomeric excess of chiral starting materials is one of the important factors determining the enantiopurity of products in asymmetric synthesis. Fifty‐one commercially available chiral reagents used as building blocks, catalysts, and auxiliaries in various enantioselective syntheses were assayed for their enantiomeric purity. The test results were classified within five impurities level (ie, <0.01%, 0.01%‐0.1%, 0.1%‐1%, 1%‐10%, >10%). Previously from 1998 to 2013, several reports have been published on the enantiomeric composition of more than 300 chiral reagents. This series of papers is necessitated by the fact that new reagents are forthcoming and that the enantiomeric purity of the same reagent can vary from batch to batch and/or from supplier to supplier. This report presents chiral liquid chromatography (LC) and gas chromatography (GC) methods to separate enantiomers of chiral compounds and evaluate their enantiomeric purities. The accurate and efficient LC analysis was done using newly introduced superficially porous particle (SPP 2.7 μm) based chiral stationary phases (TeicoShell, VancoShell, LarihcShell‐P, and NicoShell).

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Macrocyclic Antibiotics and Cyclofructans

Aslani

Berthod

Armstrong

2023

Chiral Separations and Stereochemical Elucidation

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Effective methodologies for enantiomeric separations of 150 pharmacology and toxicology related 1°, 2°, and 3° amines with core-shell chiral stationary phases

Cited by 42 publications

References 26 publications

Evaluation of the Edman degradation product of vancomycin bonded to core‐shell particles as a new HPLC chiral stationary phase

Evaluation of the Edman degradation product of vancomycin bonded to core‐shell particles as a new HPLC chiral stationary phase

Enantiomeric impurities in chiral catalysts, auxiliaries, and synthons used in enantioselective syntheses. Part 5

Macrocyclic Antibiotics and Cyclofructans

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