Updating a generic screening approach in sub- or supercritical fluid chromatography for the enantioresolution of pharmaceuticals

Klerck, Katrijn De; Tistaert, Christophe; Mangelings, Debby; Heyden, Yvan Vander

doi:10.1016/j.supflu.2013.04.003

Cited by 30 publications

(15 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indeed, because of the fluid density increase, the elution strength of the mobile phase increase, favoring a decrease of the retention time of the analyte, but enantioselectivity is slightly reduced. According to De Klerck et al, 22,23 a propanol-containing mobile phase provided the highest success rate, and it was favored when the CSP was Chiralpak AD-H [coated amylose tris(3,5-dimethylphenylcarbamate)], and a methanol-containing mobile phase was favored when the CSPs were Chiralpak OD-H [coated cellulose tris(3,5-dimethylphenylcarbamate)] and Chiralcel OZ-H/ Lux Cellulose 2 [coated cellulose tris(3-chloro-4methylphenylcarbamate)] in most cases; however, regardless of the acetonitrile, which was not used in their study, the alcoholic solvents demonstrated opposite resolution performances on these chiral columns with the same CSPs. 21 On the one hand, there are some differences between our work and previous studies on SFC enantioseparation.…”

Section: Selection Of Stationary and Mobile Phases For Fast Enantiomentioning

confidence: 99%

“…21 On the one hand, there are some differences between our work and previous studies on SFC enantioseparation. According to De Klerck et al, 22,23 a propanol-containing mobile phase provided the highest success rate, and it was favored when the CSP was Chiralpak AD-H [coated amylose tris(3,5-dimethylphenylcarbamate)], and a methanol-containing mobile phase was favored when the CSPs were Chiralpak OD-H [coated cellulose tris(3,5-dimethylphenylcarbamate)] and Chiralcel OZ-H/ Lux Cellulose 2 [coated cellulose tris(3-chloro-4methylphenylcarbamate)] in most cases; however, regardless of the acetonitrile, which was not used in their study, the alcoholic solvents demonstrated opposite resolution performances on these chiral columns with the same CSPs. It is obviously that a methanol-containing mobile phase was favored when the column was AMY1, which has the same CSP with Chirapak AD-H, and a 2propanol-containing mobile phase was favored when the columns were CEL1 and CEL2, which have the same CSPs with Chiralpak OD-H and Chiralcel OZ-H/Lux Cellulose 2.…”

Section: Selection Of Stationary and Mobile Phases For Fast Enantiomentioning

confidence: 99%

See 1 more Smart Citation

Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism

et al. 2018

View full text Add to dashboard Cite

Supercritical fluid chromatography (SFC) is already used for enantioseparation in the pharmaceutical industry, but it is rarely used for the separation of chiral pesticides. Comparing with high performence liquid chromatography, SFC uses much more environmnetal friendly and economic mobile phase, supercritical CO . In our work, the enantioseparation of an amide herbicide, napropamide, using three different polysaccharide-type chiral stationary phases (CSPs) in SFC was investigated. By studying the effect of different CSPs, organic modifiers, temperature, back-pressure regulator pressures, and flow rates for the enantioseparation of napropamide, we established a rapid and green method for enantioseparation that takes less than 2 minutes: The column was CEL2, the mobile phase was CO with 20% 2-propanol, and the flow rate was 2.0 mL/min. We found that CEL2 demonstrated the strongest resolution capability. Acetonitrile was favored over alcoholic solvents when the CSP was amylose and 2-propanol was the best choice when using cellulose. When the concentration of the modifiers or the flow rate was decreased, resolutions and analysis times increased concurrently. The temperature and back-pressure regulator pressure exhibited only minor influences on the resolution and analysis time of the napropamide enantioseparations with these chiral columns. The molecular docking analysis provided a deeper insight into the interactions between the enantiomers and the CSPs at the atomic level and partly explained the reason for the different elution orders using the different chiral columns.

show abstract

Section: Selection Of Stationary and Mobile Phases For Fast Enantiomentioning

confidence: 99%

Section: Selection Of Stationary and Mobile Phases For Fast Enantiomentioning

confidence: 99%

Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Because the market for CSP is a dynamic one, and more CSP have been commercialized, recent work has focused on the evaluation of recently commercialized CSP for their enantioselectivity and their potential to be included in existing separation strategies. This has resulted in updated strategies for POSC (Ates et al ., ; Younes et al ., ), RPLC (Younes et al ., , ), NPLC (Younes et al ., , ), CEC (Hendrickx et al ., ) and SFC (De Klerck et al ., ).…”

Section: Introductionmentioning

confidence: 97%

Chiral separability of boron cluster species studied by screening approaches utilizing polysaccharide‐based chiral stationary phases

Mangelings

Heyden

Vespalec

2014

Biomedical Chromatography

View full text Add to dashboard Cite

In this study, the screening steps of chiral separation strategies with polysaccharide-based chiral stationary phases were applied on boron cluster compounds in normal-phase liquid chromatography (NPLC) and polar organic solvents chromatography (POSC). Since the screening steps were initially developed to analyze organic compounds, their applicability for boron clusters was investigated. Overall, the screening steps in NPLC were applicable for the separation of zwitterions, while for anions mostly no elution was observed. A hypothesis for the latter behavior is precipitation of anions in the nonpolar mobile phases. Ten out of 11 compounds could be partially or baseline separated on the NPLC screening systems. In POSC, all zwitterions were separated on at least one of the screening systems, with an overall lower retention as in NPLC. Anions were detected but not separated in the majority of the experiments. Also their retention on the chiral stationary phases was very limited. This study showed that the chiral discrimination potential of chemically modified polysaccharides is meaningful for chiral separations of structurally chiral boron cluster species, but needs further systematic research, in which recognition mechanisms should be further explored. In addition, some unusual peaks also indicated that conditions with a high separation efficiency must first be searched for some of the tested systems.

show abstract

Section: Introductionmentioning

confidence: 99%

“…In order to face the challenges of a continuously increasing number of separation requests, it is important to have a strategic approach to efficiently screen the compounds to quickly find a chromatographic method that can be used for a preparative separation. [10][11][12][13][14] Screening on a large number of columns and mobile phases would give the best combination of conditions, but is also very time-consuming. On the other hand, by screening a small set of column and mobile phase combinations, important information can be lost and combinations giving high resolution might not be found.…”

Section: Introductionmentioning

confidence: 99%

A hierarchical screening approach to enantiomeric separation

et al. 2017

View full text Add to dashboard Cite

The screening of a number of chiral stationary phases (CSPs) with different modifiers in supercritical fluid chromatography to find a chromatographic method for separation of enantiomers can be time-consuming. Computational methods for data analysis were utilized to establish a hierarchical screening strategy, using a dataset of 110 drug-like chiral compounds with diverse structures tested on 15 CSPs with two different modifiers. This dataset was analyzed using a combinatorial algorithm, principal component analysis (PCA), and a correlation matrix. The primary goal was to find a set of eight columns resolving a large number of compounds, but also having complementary enantioselective properties. In addition to the hereby defined hierarchical experimental strategy, quantitative structure enantioselective models (QSERs) were evaluated. The diverse chemical space and relatively limited size of the training set reduced the accuracy of the QSERs. However, including separation factors from other CSPs increased the accuracies of the QSERs substantially. Hence, such combined models can support the experimental strategy in prioritizing the CSPs of the second screening phase, when a compound is not separated by the primary set of columns.

show abstract

Updating a generic screening approach in sub- or supercritical fluid chromatography for the enantioresolution of pharmaceuticals

Cited by 30 publications

References 17 publications

Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism

Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism

Chiral separability of boron cluster species studied by screening approaches utilizing polysaccharide‐based chiral stationary phases

A hierarchical screening approach to enantiomeric separation

Contact Info

Product

Resources

About