3-Fluoro-, 3-chloro- and 3-bromo-5-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for high-performance liquid chromatographic enantioseparation

Chankvetadze, Bezhan; Chankvetadze, Lali; Sidamonidze, Shota; Kasashima, Eiji; Yashima, Eiji; Okamoto, Yoshio

doi:10.1016/s0021-9673(97)00648-1

Cited by 131 publications

(91 citation statements)

References 20 publications

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“…Contrary to cellulose, left-handed 4/1 helical structure is postulated for amylose [113]. 3-Fluoro-, 3-chloro and 3-bromo-5-methylphenylcarbamated of cellulose and amylose as CSPs were investigated by Chankvetadze et al [114] and were found to show better chiral recognition ability than the corresponding 3,5-difluoro-and 3,5-dimethylphenylcarbamates.…”

Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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“…Indeed, past studies indicated that chlorine-containing phases would show additional enantiorecognition abilities compared to the polysaccharide-based selectors without chlorine. 8 Moreover, a chlorine-containing cellulosic CSP (Sepapak-2) showed enantioselectivity for some compounds which could not be resolved by the selectors without chlorine. 9 Thus including such phases in a screening strategy could improve success rates.…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of phospine‐containing α‐amino acid derivatives using two complementary cellulosic stationary phases in supercritical fluid chromatography

et al. 2009

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Enantiomeric separations of six amino-acid derivatives have been studied using packed-column supercritical fluid chromatography with two polysaccharide-based enantioselective stationary phases: cellulose tris(3,5-dimethylphenylcarbamate) and cellulose tris(3-chloro-4-methylphenylcarbamate) (Lux Cellulose-1 and -2). The effect of analyte structure on retention and separation was studied. Varied mobile phase compositions were investigated: alcohol modifier percentage was increased from 3 to 40% but smaller amounts were most effective in separating these compounds. Besides, ethanol was preferred to methanol or isopropanol as it proved to be a good compromise to achieve sufficient resolution in a reasonable analysis time. Moreover, a carbon dioxide-ethanol mixture allows performing analyses in safe and green conditions. The effect of temperature at constant mobile phase composition was explored between 10 and 40 degrees C. In most cases, increasing the temperature improved the chiral separation, up to an optimum temperature. The results are discussed in line with the structure variation of the racemic derivatives analyzed and the two columns are compared. The two columns were shown to provide complementary selectivities for the investigated solutes: whereas Lux 1 provided separation for five of the six racemates, Lux 2 could resolve the last racemic mixture. Finally, optimized conditions of separation are defined.

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“…Of the these, cellulose tris-(3,5-dimethylpheyl-carbamate) (CDMPC) offered the highest enantiomeric separability [12]. In another investigation on chiral recognition ability of cellulose phenylcarbamate derivatives, cellulose-tris-(3-fluoro-5-methylphenylcarbamate) was reported to be better than 3,5-difluoro-and 3,5-dimethylphenylcarbamates of cellulose for enantioseparation of ten racemates [13].…”

Section: The Development Of Coated Cellulose-based Cspsmentioning

confidence: 99%