Preparation of a new immobilized cellulose-based chiral stationary phase and its enantioseparation behaviors

Abstract

The immobilized polysaccharide-based chiral stationary phase has attracted considerable attention over the past decades due to its high chemical stability, good solvent resistance, great enantioseparation ability, etc. In this study, a new immobilized cellulose chiral stationary phase (denoted as ImCel) was prepared through the Staudinger reaction of 6-azido-6-deoxy-cellulose-3,5-dichlorophenylcarbamate and aminopropyl silica gel. The enantioseparation performance of the ImCel for 20 pairs of chiral analytes and the effect of non-standard solvents have been investigated by high performance liquid chromatography. Baseline separations of 17 pairs of enantiomers were achieved on the ImCel. The separation ability of the ImCel in the normal mode was much better than in reversed mode. In addition, the ImCel showed good chemical stability in the non-standard mobile phase due to the covalent bonds between the cellulose chiral selectors and silica support. Moreover, it exhibited complementarity with another immobilized-cellulose chiral stationary phase containing 3, 5-dimethylphenylcarbamate groups for the separation of a series of 9-fluorenylmethyloxycarbonyl (fmoc) -derived amino acids. The reversal of enantiomer elution order induced by the difference of the substituents in chiral stationary phase was observed under the same chromatographic conditions. In brief, a new immobilized cellulose chiral stationary phase with high stability and good separation performance was developed in this work.