Chromatographic resolution. 7. Useful chiral packing materials for high-performance liquid chromatographic resolution of enantiomers: phenylcarbamates of polysaccharides coated on silica gel

Okamoto, Yoshio; Kawashima, M.; Hatäda, Koichi

doi:10.1021/ja00330a057

Cited by 477 publications

(206 citation statements)

References 0 publications

Supporting

Mentioning

191

Contrasting

Unclassified

Order By: Relevance

“…Francotte and Wolf [108] prepared spherical beads of cellulose tribenzoate derivatives for preparative LC. Okamoto's group developed a series of CSPs based on cellulose trisphenylcarbamate derivatives (CTPCs) adsorbed to macroporous silica [109]. The chiral recognition mechanism on CTPC phases was elucidated by X-ray analysis, NMR studies [110,111] and computer simulations [38].…”

Section: Direct Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

223

135

View full text Add to dashboard Cite

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.

show abstract

Section: Direct Methodsmentioning

confidence: 99%

“…Besides cellulose and amylose other polysaccharides such as, chitosan [109,122], chitin [123] and amylopectin [124] were used for the preparation of CSPs.…”

Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

223

135

View full text Add to dashboard Cite

show abstract

“…1 One of the major problems in using many CSPs is their narrow range of analyte applicability; they can only discriminate a limited number of specific types of chemical entities, and it is frequently necessary to derivatize the compounds of interest to achieve separation. 2 On the other hand, the polysaccharide derivative-based CSPs developed by Okamoto and coworkers [3][4][5][6][7] have proven to be highly versatile and rugged. Okamoto reported that the resolution of 483 racemic mixtures on cellulose and that 80% of them were successfully resolved on either the cellulose or amylose tris(3,5-dimethylphenylcarbamate) (CDMPC or ADMPC).…”

mentioning

confidence: 99%

Cellulose Dimethylphenylcarbamate-bonded Carbon-clad Zirconia for Chiral Separation in High Performance Liquid Chromatography

et al. 2006

Self Cite

View full text Add to dashboard Cite

HPLC based on chiral stationary phases (CSPs) has become one of the most attractive approaches to chiral separations, due to their simplicity for determining optical purity and easy extension to the semipreparative and preparative scales. 1 One of the major problems in using many CSPs is their narrow range of analyte applicability; they can only discriminate a limited number of specific types of chemical entities, and it is frequently necessary to derivatize the compounds of interest to achieve separation. 2 On the other hand, the polysaccharide derivative-based CSPs developed by Okamoto and coworkers [3][4][5][6][7] have proven to be highly versatile and rugged. Okamoto reported that the resolution of 483 racemic mixtures on cellulose and that 80% of them were successfully resolved on either the cellulose or amylose tris(3,5-dimethylphenylcarbamate) (CDMPC or ADMPC). 8 Silica is the most popular choice for support of HPLC stationary phase ligands due to the mechanical strength, wide range of particle and pore dimensions, pore structure and wellestablished silane chemistry. However, silica and bonded phase ligands have stability problems. Silica dissolves in mobile phase buffered at or above pH 8 with loss of bonded phase ligand and column packing. 9 Loss of organosilanes from the silica surface via hydrolysis proceeds rapidly at low pH (< 3) and at high temperature (≥ 40˚C). These deficiencies of the column packing create problems of poor injection reproducibility, poor peak shape, and high backpressure, thus making method development tasks difficult. Siloxane-bonded silica phases with improved hydrolytic stability at extreme pH for use in reversedphase liquid chromatography were introduced. 10-13 However, careful choices of operating conditions, such as the use of acetonitrile instead of methanol, the use of boric acid or organic buffers in low concentration and low temperature, are still required to achieve acceptable column lifetimes. [14][15][16][17] Zirconia particles are very robust material; they show no detectable signs of dissolution over the pH range from 1 to 14 and have been used for prolonged periods at temperatures up to 200˚C in chromatographic separations. Thus, zirconia has received considerable attention as a stationary phase support for HPLC over the last decade. 18,19 One of us has been working to develop efficient and chemically stable CSPs on zirconia substrates. [20][21][22][23] Bare zirconia cannot be covalently modified like silica due to the instability of Zr-C and Zr-O-Si bonds in water. 24 Zirconia-based CSPs reported have thus been prepared by coating chiral selectors on zirconia surface by utilizing Lewis acid-base chemistry. Recently we reported chiral separation of N- (2,4-dinitrophenyl) Porous zirconia particles are very robust material and have received considerable attention as a stationary phase support for HPLC. We prepared cellulose dimethylphenylcarbamate-bonded carbon-clad zirconia (CDMPCCZ) as a chiral stationary phase (CSP) for separation of enantiomers of a set of...

show abstract

“…1 For example, CSPs based on cellulose derivatives, 2 cyclodextrins, 3 macro cyclic antibiotics, 4 chiral crown ethers 5 and low molecular mass π-acidic or π-basic chiral molecules 6 have been successfully utilized in the determination of enantiomeric composition of chiral compounds.…”

mentioning

confidence: 99%