Preparation of a positively charged cellulose derivative chiral stationary phase with copolymerization reaction for capillary electrochromatographic separation of enantiomers

Abstract

A positively charged chiral stationary phase (CSP) was prepared by chemically immobilizing cellulose 3,5-dimethylphenylcarbamate onto methacryloyldiethylenetriaminopropylated silica (MCDEAPS) via a radical copolymerization reaction. The prepared CSP was evaluated for enantiomer separation in nonaqueous capillary electrochromatography (CEC). Electroosmotic flow (EOF) generated on the prepared CSP could be significantly improved with introduction of positive charges into the CSP, and separation of enantiomers in CEC has been achieved with mobile phases of ethanol and hexane-ethanol, respectively. In addition, we investigated the solvent versatility of the immobilized CSP on enantioseparations in CEC and capillary liquid chromatography (CLC) due to the elimination of dissolution of chiral selector in a number of solvents. Chiral resolution of some enantiomers was improved by adopting tetrahydrofuran (THF) and chloroform as mobile-phase modifiers, respectively.

Monolithic silica capillary column with coated cellulose tris(3,5‐dimethylphenylcarbamate) for capillary electrochromatographic separation of enantiomers

“…Recently, those kinds of CSPs were also transferred to CEC. Packed-column CEC with coated or bonded cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) [14,[25][26][27][28][29][30][31][32], cellulose tris(4-methylbenzoate) [33,34], cellulose tris(3,5-dichlorophenylcarbamate) [35][36][37][38], and amylose (3,5-dimethylphenylcarbamate) [27,34,39] were reported by several research groups. Surprisingly, no attention has been paid to the polysaccharide derivative-based monolithic CSPs for CEC separation, although Chankvetadze et al [40][41][42] reported promising application of such kinds of columns in HPLC and CLC.…”

Polyacrylamide‐based monolithic capillary column with coating of cellulose tris(3,5‐dimethylphenyl‐carbamate) for enantiomer separation in capillary electrochromatography

“…In CEC, cellulose derivatives including cellulose tris(3,5-dimethylphenyl-carbamate) (CDMPC) [10,[28][29][30], cellulose tris(4-methylbenzoate) [31,32], cellulose tris(3,5-dichlorophenylcarbamate) [33][34][35], and amylase(3,5-dimethylphenylcarbamate) [31,32] have also been used for the separations of enantiomers via coating or bonding on silica-based particulate packed columns or monolithic column. Interestingly, little has been reported on the use of cellulose derivatives, such as CDMPC, for the preparation of hydrophilic organic polymeric monolithic CSPs in CEC.…”

Recent accomplishments in the field of enantiomer separation by CEC

“…warfarin). In another study, the authors employed a radical copolymerization reaction for the covalent immobilization of a cellulose carbamate derivative [50]. Hence, cellulose 2,3-bis(3,5-dimethylphenylcarbamate)-6-methacrylate was synthesized and grafted onto N-methacryloyl-modified DEAPS.…”