Screening approach for chiral separation of pharmaceuticals

Matthijs, Nele; Maftouh, Mohamed; Heyden, Yvan Vander

doi:10.1016/j.chroma.2006.01.106

Cited by 187 publications

(72 citation statements)

References 39 publications

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“…References [26 -29, 31 -33] describe the screening-and optimisation strategies developed in NPLC, RPLC, SFC, and CE. For the fifth technique, POSC, only initial screening conditions have so far been described [30]. This technique has proved to be interesting on account of its efficient separations and short analysis times [18,30].…”

Section: Introductionmentioning

confidence: 98%

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Chiral separation strategy in polar organic solvent chromatography and performance comparison with normal‐phase liquid and supercritical‐fluid chromatography

Matthijs

Maftouh

Heyden³

2006

J of Separation Science

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A strategy, including a rapid screening and several optimisation steps, for the separation of chiral molecules of pharmaceutical interest by polar organic solvent chromatography (POSC), using four polysaccharide-based stationary phases, is proposed and compared with previously reported strategies in normal-phase (NPLC) and supercritical fluid chromatography (SFC). In a first part of this paper, different examples demonstrate the effectiveness of the POSC strategy for fast method development. Optimisation is based on the use of experimental design to map the experimental domain in an efficient way. In the second part, the best screening results, obtained after performance of earlier defined chromatographic screening strategies in NPLC and SFC, are compared to those obtained in POSC. The three techniques show complementary separation results and allowed baseline separation of 23 of 25 compounds. POSC is found to be a very interesting separation mode compared to NPLC, because of the many fast (< 10 min) baseline separations obtained.

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Section: Introductionmentioning

confidence: 98%

“…The techniques included are normal-phase LC (NPLC) [26 -27], RPLC [26 -28], SFC [29], POSC [30], and CE [31 -33]. Only four types of polysaccharide columns are used for screening by the four chromatographic techniques.…”

Section: Introductionmentioning

confidence: 99%

Chiral separation strategy in polar organic solvent chromatography and performance comparison with normal‐phase liquid and supercritical‐fluid chromatography

Matthijs

Maftouh

Heyden³

2006

J of Separation Science

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“…The tris-(3,5-dimethylphenyl carbamate) derivative of cellulose adsorbed on silica gel can be used with both organic or water-based eluents (Chiralcel OD-RH). [72][73][74][75][76] Macrocyclic antibiotics, like vancomycin and teicoplanin, represent a relatively new class of chiral selectors showing enantioselectivity for several compound classes. Teicoplanin aglycon, like the parent glycopeptide, has been immobilized onto silica gel microparticles (Chirobiotic TAG) and used as a HPLC chiral selector [77][78][79][80] with excellent chiral recognition abilities and wide application range (see Fig.…”

Section: Resultsmentioning

confidence: 99%

Effective HPLC resolution of [4]heterohelicenium dyes on chiral stationary phases using reversed‐phase eluents

et al. 2006

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[4]Heterohelicenium cations 1a-c adopt a twisted helical structure that renders them chiral. They are configurationally stable and their enantiomers have been resolved, for the first time, by HPLC on Chiralcel OD-RH and Chirobiotic TAG chiral stationary phases (CSPs). Chiral cations 1a-c have been resolved by HPLC using water-based eluents containing KPF(6) as additive. The elution order of the analyte enantiomers was determined by on-line CD detection, and was found to be opposite on the two CSPs. The effect of mobile phase composition and analyte structure on retention and enantioselectivity was investigated.

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“…Nonconventional solvent mixtures of 20% EtOH with tert-butyl methyl ether or chloroform as well as the recently developed polar-mode elution 22 were also unsuccessful in the enantioseparation of (6)-1 on Chiralpak IB. Furthermore, some eluent mixtures developed high back pressure in the column giving some limitation in the allowable flow rate.…”

Section: Sample Preparationmentioning

confidence: 98%

Chiral HPLC analysis of milnacipran and its FMOC‐derivative on cellulose‐based stationary phases

2007

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The HPLC enantioseparation of the last generation antidepressive drug milnacipran (+/-)-1 was investigated on different cellulose-based chiral stationary phases (CSPs). On carbamate-type columns, Chiralcel OD and OD-H (+/-)-1 could be separated with alpha value about 1.20 but the resolution was quite low because of the tailing of the peaks. Direct determination of (+/-)-1 with high selectivity and resolution was obtained on Chiralcel OJ in normal phase mode elution. Precolumn derivatization of milnacipran with Fmoc-Cl gave compound (+/-)-2 which was enantioseparated on all the investigated CSPs and allowed enhanced UV or fluorimetric detection. The Chiralpak IB, that could be considered the immobilized version of Chiralcel OD-H, was found completely ineffective in the chiral recognition of (+/-)-1 and moderately efficient in the separation of (+/-)-2.

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Screening approach for chiral separation of pharmaceuticals

Cited by 187 publications

References 39 publications

Chiral separation strategy in polar organic solvent chromatography and performance comparison with normal‐phase liquid and supercritical‐fluid chromatography

Chiral separation strategy in polar organic solvent chromatography and performance comparison with normal‐phase liquid and supercritical‐fluid chromatography

Effective HPLC resolution of [4]heterohelicenium dyes on chiral stationary phases using reversed‐phase eluents

Chiral HPLC analysis of milnacipran and its FMOC‐derivative on cellulose‐based stationary phases

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