A comprehensive methodology for the chiral separation of 40 tobacco alkaloids and their carcinogenic E/Z-(R,S)-tobacco-specific nitrosamine metabolites

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

doi:10.1016/j.talanta.2017.12.060

Cited by 28 publications

(17 citation statements)

References 44 publications

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“…The method was successfully applied for the determination of the enantiomeric ratio of nicotine in various tobacco products. This approach was further elaborated for the analysis of nicotine-related compounds [ 73 ]. Complementary separations were seen in several cases using macrocyclic antibiotic-based commercial columns (VancoShell, TeicoShell, NicoShell, AZYP, LLC, Arlington, TX, USA) offering the possibility for high-throughput investigations.…”

Section: Recent Applications Of Different Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

et al. 2021

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Numerous chemical compounds of high practical importance, such as drugs, fertilizers, and food additives are being commercialized as racemic mixtures, although in most cases only one of the isomers possesses the desirable properties. As our understanding of the biological actions of chiral compounds has improved, the investigation of the pharmacological and toxicological properties has become more and more important. Chirality has become a major issue in the pharmaceutical industry; therefore, there is a continuous demand to extend the available analytical methods for enantiomeric separations and enhance their efficiency. Direct liquid chromatography methods based on the application of chiral stationary phases have become a very sophisticated field of enantiomeric separations by now. Hundreds of chiral stationary phases have been commercialized so far. Among these, macrocyclic glycopeptide-based chiral selectors have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance. This review focuses on direct liquid chromatography-based enantiomer separations, applying macrocyclic glycopeptide-based chiral selectors. Special attention is paid to the characterization of the physico-chemical properties of these macrocyclic glycopeptide antibiotics providing detailed information on their applications published recently.

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Section: Recent Applications Of Different Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

et al. 2021

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“…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%

“…Some studies have been done with modified macrocyclic glycopeptides, such as the crystalline degradation of vancomycin, which incorporates a second carboxylic acid moiety in the structure . 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 .…”

Section: Introductionmentioning

confidence: 99%

“…20 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]). [21][22][23][24][25] This has been particularly useful to ultrafast chiral separations needed in second dimension (2D) LC. [24][25][26][27][28][29] However, many glycopeptides are costly and have limited availability, which has led to a need to understand the applicability and limitations of more available glycopeptides so further exploration can be made concerning useful modifications.…”

Section: Introductionmentioning

confidence: 99%

“…[30][31][32] Recently, a modified macrocyclic glycopeptidebased 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. 21,22 NicoShell was further utilized for the separation of several chiral amines. 23 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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Macrocyclic Antibiotics and Cyclofructans

Aslani

Berthod

Armstrong

2023

Chiral Separations and Stereochemical Elucidation

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A comprehensive methodology for the chiral separation of 40 tobacco alkaloids and their carcinogenic E/Z-(R,S)-tobacco-specific nitrosamine metabolites

Cited by 28 publications

References 44 publications

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

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

Macrocyclic Antibiotics and Cyclofructans

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