Hysteresis of retention and enantioselectivity on amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phases in mixtures of 2-propanol and methanol

Horváth, Simon; Németh, Gábor

doi:10.1016/j.chroma.2018.07.033

Cited by 27 publications

(13 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, these history dependent differences were checked and also observed on Lux Amylose-1 column with the same chiral selector (amylose tris(3,5-dimethylphenylcarbamate) as the Chiralpak AD column. Our results confirm the recently reported observations by Horváth et al [21] regarding the combination of MeOH/IPA as eluents, and further extend the possible mobile phase combinations displaying hysteretic behaviour to other mobile phase mixtures, such as MeOH/PROP, MeOH/ACN and EtOH/ACN. Thus, results indicate that the hysteretic behaviour on coated CSPs having amylose tris(3,5-dimethylphenylcarbamate) as chiral selectors is general, and it is not limited to the MeOH/IPA mixtures, but rather are more prominent in this system.…”

Section: Enantioseparation Of Mobile Phase Mixtures Hysteresis Of Ret...supporting

confidence: 92%

“…It seems that the selectivity of the separation systems is highly influenced by the solvent that is used during the pre-conditioning of the CSP. This hysteretic behavior was described recently, and it was suggested that the history of eluents used previously on the column may alter the enantioselective environment of chiral selector by causing hindrance transition in the higher order structure of the CSP [ 21 , 22 ]. The hindrance transition effect in the structure of chiral selector can be explained by affecting the H-bond system through the application of different eluents.…”

Section: Resultsmentioning

confidence: 97%

“…Whenever an experiment required pre-treatment with either IPA, MeOH, EtOH or ACN, this was brought about by pumping 10 column volumes (CV) of the corresponding solvent through the column. Regarding hysteresis study we follow the protocol of the work of Németh and Simon [ 21 ]. In this work, the effect of different equilibration volumes (10 CV, 20 CV, 100 CV, 800 CV, 1600 CV and 2400 CV) on chromatographic behaviour were also tested.…”

Section: Methodsmentioning

confidence: 99%

“…In a recent article, Horváth et al demonstrated that different mixtures of MeOH and IPA as a mobile phase can alter the structure of the amylose tris(3,5-dimethylphenylcarbamate) chiral selector, resulting in EEO reversals, depending on the IPA/MeOH proportions. Besides EEO reversal, a very interesting phenomenon called hysteresis was also observed on columns containing the abovementioned chiral selector: enantioselectivities and analyte retention times depended on the direction from which the composition (IPA or MeOH) of the eluent was approached [ 21 ]. This observation can be utilized as a novel screening method in PO mode [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Comparative Chiral Separation of Thalidomide Class of Drugs Using Polysaccharide-Type Stationary Phases with Emphasis on Elution Order and Hysteresis in Polar Organic Mode

et al. 2021

View full text Add to dashboard Cite

The enantioseparation of four phthalimide derivatives (thalidomide, pomalidomide, lenalidomide and apremilast) was investigated on five different polysaccharide-type stationary phases (Chiralpak AD, Chiralpak AS, Lux Amylose-2, Chiralcel OD and Chiralcel OJ-H) using neat methanol (MeOH), ethanol (EtOH), 1-propanol (PROP), 2-propanol (IPA) and acetonitrile (ACN) as polar organic mobile phases and also in combination. Along with the separation capacity of the applied systems, our study also focuses on the elution sequences, the effect of mobile phase mixtures and the hysteresis of retention and selectivity. Although on several cases extremely high resolutions (Rs > 10) were observed for certain compounds, among the tested conditions only Chiralcel OJ-H column with MeOH was successful for baseline-separation of all investigated drugs. Chiral selector- and mobile-phase-dependent reversals of elution order were observed. Reversal of elution order and hysteresis of retention and enantioselectivity were further investigated using different eluent mixtures on Chiralpak AD, Chiralcel OD and Lux Amylose-2 column. In an IPA/MeOH mixture, enantiomer elution-order reversal was observed depending on the eluent composition. Furthermore, in eluent mixtures, enantioselectivity depends on the direction from which the composition of the eluent is approached, regardless of the eluent pair used on amylose-based columns. Using a mixture of polar alcohols not only the selectivities but the enantiomer elution order can also be fine-tuned on Chiralpak AD column, which opens up the possibility of a new type of chiral screening strategy.

show abstract

Section: Enantioseparation Of Mobile Phase Mixtures Hysteresis Of Ret...supporting

confidence: 92%

Section: Resultsmentioning

confidence: 97%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Comparative Chiral Separation of Thalidomide Class of Drugs Using Polysaccharide-Type Stationary Phases with Emphasis on Elution Order and Hysteresis in Polar Organic Mode

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Recently, Németh and Horváth observed isothermal hysteresis phenomena of retention and enantioselectivity on ADMPC using mixtures of 2-propanol and methanol [106]. On the basis of chromatographic results and van't Hoff analyses, the authors concluded that the only realistic mechanism to account for the hysteresis is a hindered transition of the high-ordered stucture of ADMPC.…”

Section: Intramolecular Hydrogen Bonds and High-ordered Structure Of mentioning

confidence: 99%

Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors

Peluso

Mamane

Dallocchio

et al. 2020

Journal of Chromatography A

View full text Add to dashboard Cite

HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

show abstract

Comparative enantioseparation of planar chiral ferrocenes on polysaccharide‐based chiral stationary phases

et al. 2022

View full text Add to dashboard Cite

Planar chiral ferrocenes are well‐known compounds that have attracted interest for application in synthesis, catalysis, material science, and medicinal chemistry for several decades. In spite of the fact that asymmetric synthesis procedures for obtaining enantiomerically enriched ferrocenes are available, sometimes, the accessible enantiomeric excess of the chiral products is unsatisfactory. In such cases and for resolution of racemic planar chiral ferrocenes, enantioselective high‐performance liquid chromatography (HPLC) on polysaccharide‐based chiral stationary phases (CSPs) has been used in quite a few literature articles. However, although moderate/high enantioselectivities have been obtained for planar chiral ferrocenes bearing polar substituents, the enantioseparation of derivatives containing halogens, or exclusively alkyl groups, remains rather challenging. In this study, the enantioseparation of ten planar chiral 1,2‐ and 1,3‐disubstituted ferrocenes was explored by using five polysaccharide‐based CSPs under multimodal elution conditions. Baseline enantioseparations were achieved for nine analytes with separation factors (α) ranging from 1.20 to 2.92. The presence of π‐extended systems in the analyte structure was shown to impact affinity of the most retained enantiomer toward amylose‐based selectors, observing retention times higher than 80 min with methanol‐containing mobile phases (MPs). Electrostatic potential (V) analysis and molecular dynamics (MD) simulations were used in order to study interaction modes at the molecular level.

show abstract

Hysteresis of retention and enantioselectivity on amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phases in mixtures of 2-propanol and methanol

Cited by 27 publications

References 52 publications

Comparative Chiral Separation of Thalidomide Class of Drugs Using Polysaccharide-Type Stationary Phases with Emphasis on Elution Order and Hysteresis in Polar Organic Mode

Comparative Chiral Separation of Thalidomide Class of Drugs Using Polysaccharide-Type Stationary Phases with Emphasis on Elution Order and Hysteresis in Polar Organic Mode

Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors

Comparative enantioseparation of planar chiral ferrocenes on polysaccharide‐based chiral stationary phases

Contact Info

Product

Resources

About