Supercritical fluid chromatography comparison of the poly(trans-1,2-cyclohexanediyl-bis acrylamide) (P-CAP) column with several derivatized polysaccharide-based stationary phases☆

Barnhart, Wesley W.; Gahm, Kyung H.; Zheng, Hongyan; Goetzinger, Wolfgang

doi:10.1016/j.jchromb.2008.08.029

Cited by 15 publications

(6 citation statements)

References 24 publications

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“…There are several HPLC methods using different types of CSPs for 1 , 2 , and 3 [ 7 , 16 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ]. Relatively few studies have been reported on the synthesis and chiral enantioseparation of 4 [ 31 , 32 , 33 , 34 , 35 , 36 ]. Although the piecemeal chiral separation of these compounds was previously reported, a systematic and comprehensive study is beneficial to seek for general clues to the separation of chiral sulfoxide drugs.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs

et al. 2018

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The distinct pharmacodynamic and pharmacokinetic properties of enantiopure sulfoxide drugs have stimulated us to systematically investigate their chiral separation, stereochemical assignment, and chiral recognition mechanism. Herein, four clinically widely-used sulfoxide drugs were chosen and optically resolved on various chiral stationary phases (CSPs). Theoretical simulations including electronic circular dichroism (ECD) calculation and molecular docking were adopted to assign the stereochemistry and reveal the underlying chiral recognition mechanism. Our results showed that the sequence of calculated mean binding energies between each pair of enantiomers and CSP matched exactly with experimentally observed enantiomeric elution order (EEO). It was also found that the length of hydrogen bond might contribute dominantly the interaction between two enantiomers and CSP. We hope our study could provide a fresh perspective to explore the stereochemistry and chiral recognition mechanism of chiral drugs.

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Section: Introductionmentioning

confidence: 99%

Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs

et al. 2018

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“…The commercially available compounds were compiled from referencing previous evaluations of novel CSPs [20][21][22]. Of the commercial compounds selected, 11 were neutral, 4 were acidic and 9 were basic, see Fig.…”

Section: Resultsmentioning

confidence: 99%

A high throughput approach to purifying chiral molecules using 3μm analytical chiral stationary phases via supercritical fluid chromatography

Hamman¹,

Wong²,

Hayes³

et al. 2011

Journal of Chromatography A

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“…In discovery laboratories, it is not uncommon that achiral impurities in a complex racemic mixture make chiral resolution more difficult due to an extended injection cycle or requiring a second purification 39. As demonstrated in the example of a theophylline and caffeine mixture in the previous section, differential solubility enhancement of a compound in various SCF conditions can make SFE an alternative approach to chromatographic techniques to obtain pure material.…”

Section: Resultsmentioning

confidence: 99%

Development of supercritical fluid extraction and supercritical fluid chromatography purification methods using rapid solubility screening with multiple solubility chambers

et al. 2011

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Rapid solubility screening in diverse supercritical fluids (SCFs) was carried out via multiple solubility chambers with a trapping device and online ultraviolet (UV) detection. With this device, it was possible to rapidly study the solubility variations of multiple components in a mixture. Results from solubility studies have been used to develop efficient supercritical fluid extraction (SFE) and supercritical fluid chromatography (SFC) methods. After the investigation of solubilities of theophylline and caffeine in several neat organic solvents and SCFs, advantages of SFE over conventional organic solvent extraction were demonstrated with a model mixture of theophylline and caffeine. The highest solubility ratio of 1:40 (theophylline:caffeine) was observed in the SCF with 20% acetonitrile (MeCN), where a ratio of 1:11 was the highest in the neat organic solvents. A model mixture of theophylline:caffeine (85:15 w/w, caffeine as an impurity) was successfully purified by SFE by leveraging the highest solubility difference. The SCF with 20% MeCN selectively removed caffeine and left theophylline largely intact. Rapid SCF solubility screening was applied to development of SFE and SFC methods in a drug discovery environment. Two successful applications were demonstrated with proprietary Amgen compounds to either remove an achiral impurity before chiral purification or enhance chiral chromatographic throughput.

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Supercritical fluid chromatography comparison of the poly(trans-1,2-cyclohexanediyl-bis acrylamide) (P-CAP) column with several derivatized polysaccharide-based stationary phases☆

Cited by 15 publications

References 24 publications

Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs

Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs

A high throughput approach to purifying chiral molecules using 3μm analytical chiral stationary phases via supercritical fluid chromatography

Development of supercritical fluid extraction and supercritical fluid chromatography purification methods using rapid solubility screening with multiple solubility chambers

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