Comparative enantioseparation of selected chiral drugs on four different polysaccharide-type chiral stationary phases using polar organic mobile phases

Chankvetadze, Bezhan; Kartozia, Irma; Yamamoto, Chiyo; Okamoto, Yoshio

doi:10.1016/s0731-7085(01)00648-3

Cited by 120 publications

(48 citation statements)

References 24 publications

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“…We have been unable to discern any structural features that correlate with success. This is in agreement with the conclusions of Chankvetadze et al 6 These authors screened 20 chiral molecules on Chiralpak ADR, Chiralcel OJR, and Chiralcel ODR using neat methanol and acetonitrile mobile phases. They obtained baseline resolution for 14 compounds with resolution of at least 2.0 for 11 of the 20 probes.…”

supporting

confidence: 90%

“…This leads to the presumption that there is a different recognition mechanism involved with polar organic mobile phases. 6,7 Using polar organic mobile phases offers several advantages for preparative applications of chiral chromatography, including enhanced solubility and simplicity of operation and solvent recovery. 9 This has led to routine screening of these mobile phases at Chiral Technologies, Inc. for submitted preparative projects.…”

mentioning

confidence: 99%

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Chiral separations on polysaccharide stationary phases using polar organic mobile phases

Lynam¹,

Stringham²

2005

Chirality

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About 30% of a chemically diverse set of compounds were found to separate on four polysaccharide chiral stationary phases using polar organic mobile phases. No structural features appeared to correlate to successful separations. Titrations between normal and polar organic mobile phases suggested that separation mechanisms do not differ between these mobile phases. Attempts made to control retention met with varying degrees of success. Addition of hexane to alcohols had minor effects on retention although this was occasionally beneficial. Addition of water to alcohols increased retention. Addition of water to acetonitrile decreased retention. Addition of alcohol to acetonitrile also proved beneficial to the separation of some compounds. Loading studies performed to mimic preparative separations indicated that the benefits of polar organic mobile phases are largely due to increased solubility.

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supporting

confidence: 90%

mentioning

confidence: 99%

Chiral separations on polysaccharide stationary phases using polar organic mobile phases

Lynam¹,

Stringham²

2005

Chirality

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“…This result was interesting because the separation ability of polysaccharide-based CSPs usually decreases passing from normal-phase mode to polarorganic mode. 11,12 Thus, as reported in Figure 2, the compounds 3a and 3b respectively showed enantioselectivity factors of 2.31 and 4.19 in 2-propanol-DEA 100-0.1 (v/v) eluent and 3.15 and 1.92, in 2-propanol-based normal-phase eluents. Figure 3 shows the baseline enantioseparation of Mianserin obtained in polar-organic mode.…”

Section: Resultsmentioning

confidence: 53%

Direct HPLC enantioseparation of chiral aptazepine derivatives on coated and immobilized polysaccharide‐based chiral stationary phases

et al. 2006

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The direct HPLC enantioseparation of Mianserin and a series of aptazepine derivatives is accomplished on polysaccharide-based chiral stationary phases (CSPs). The resolutions are performed on the coated-type Chiralcel OD and Chiralpak AD CSPs and on the first commercially available immobilized-type Chiralpak IA CSP, in normal-phase and polar-organic modes. The complete separation of enantiomers of all racemates investigated was successfully achieved under at least one of CSP/eluent combinations employed. Pure alcohols such ethanol or 2-propanol, with a fixed percentage of DEA added, serve as valuable alternatives to the more common n-hexane-based normal-phase eluents in resolution of Mianserin on the AD CSP. In order to study the chiroptical properties of aptazepine derivatives, chromatographic resolutions are carried out at semipreparative scale using Chiralpak AD and Chiralpak IA as CSPs. Nonconventional dichloromethane-based eluents have permitted to expand the chiral resolving ability of the immobilized Chiralpak IA CSP and to perform mg-scale enantioseparations with an analytical-size column. Assignment of the absolute configuration of the separated enantiomers is empirically established by comparing their chiroptical data with those of structurally related Mianserin.

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“…Additionally, they are easily removed, which is especially useful in preparative-scale applications 34 and simulated moving bed chromatography. 35 When methanol was used as mobile phase on CSP2, high enantioselectivities and resolution factors were obtained for kielcorins 4 -5 and good selectivity factor but median resolution for kielcorin 1 (Table 1), while compounds 2 and 3 were partially resolved only when 2-propanol and ethanol, respectively, were used. Thus, for example, enantiomers of compound 4 were better resolved with methanol than with ethanol and 2-propanol (Rs = 2.4, 1.7, and 1.6, respectively).…”

Section: Influence Of the Mobile Phases On Enantioseparation And Enanmentioning

confidence: 96%

Enantiomeric resolution of kielcorin derivatives by HPLC on polysaccharide stationary phases using multimodal elution

et al. 2004

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Analytical HPLC methods using carbamate chiral stationary phases of polysaccharide derivatives were developed for the enantiomeric resolution of five racemic mixtures of xanthonolignoids: rac-trans-kielcorin C, rac-cis-kielcorin C, rac-trans-kielcorin D, rac-trans-isokielcorin D, and rac-trans-kielcorin E. The separations were evaluated with the stationary phases cellulose tris-3,5-dimethylphenylcarbamate, amylose tris-3,5-dimethylphenylcarbamate, amylose tris-(S)-1-phenylethylcarbamate, and amylose tris-3,5-dimethoxyphenylcarbamate under normal, reversed-phase, and polar organic elution conditions. Chiral recognition of those chiral stationary phases, the influence of mobile phases on the enantiomers separation, and the effects of structural features of the solutes on the chiral discrimination observed are discussed. The best performance was achieved on an amylose tris-3,5-dimethylphenylcarbamate phase. Polar organic conditions gave shorter retention factors and better resolutions and were a valuable alternative to the alcohol-hexane or reversed-phase conditions.

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Comparative enantioseparation of selected chiral drugs on four different polysaccharide-type chiral stationary phases using polar organic mobile phases

Cited by 120 publications

References 24 publications

Chiral separations on polysaccharide stationary phases using polar organic mobile phases

Chiral separations on polysaccharide stationary phases using polar organic mobile phases

Direct HPLC enantioseparation of chiral aptazepine derivatives on coated and immobilized polysaccharide‐based chiral stationary phases

Enantiomeric resolution of kielcorin derivatives by HPLC on polysaccharide stationary phases using multimodal elution

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