Synthesis and enantioseparation behaviors of novel immobilized 3,5-dimethylphenylcarbamoylated polysaccharide chiral stationary phases

Abstract

Two new polysaccharide-derived chiral selectors, namely, 6-azido-6-deoxy-3,5-dimethylphenylcarbamoylated amylose and 6-azido-6-deoxy-3,5-dimethylphenyl carbamoylated cellulose, were synthesized under homogeneous conditions and immobilized onto aminized silica gel by the Staudinger reaction, resulting in two new immobilized polysaccharide chiral stationary phases (CSPs). Their enantioseparation performances were investigated under normal-phase mode by HPLC. Among 17 analytes, baseline separations of 12 pairs of enantiomers are achieved on the immobilized cellulose CSP, which demonstrates that this new cellulose material exhibits almost the same enantioseparation performance as the coated cellulose CSP. In addition, the amylose-derived CSP presents limited enantiorecognition ability but certain complementarity with the immobilized and coated cellulose-based materials. Neither metolachlor nor paclitaxel side chain acids are separated on two cellulose-derived CSPs, but effective separations are obtained on the immobilized amylose column.

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

“…On the contrary, the amylose backbone of CSP 5 exhibited a beneficial effect on the enantioseparation of rac ‐ 3 (α = 1.27, R s = 1.9), which remained scarcely resolved on cellulose‐based CSP 1 ( R s = 0.4). In this regard, it needs to be considered that the immobilization process itself may induce some modification in the chromatographic properties of the resulting CSPs . Thus, the effect of immobilization has to be taken into account when the separation performances of CSP 1 and CSP 5 are compared.…”

Synthesis of new C3 symmetric amino acid‐ and aminoalcohol‐containing chiral stationary phases and application to HPLC enantioseparations

“…Various types of high‐performance liquid chromatography (HPLC) chiral stationary phases (CSPs) such as brush/Pirkle‐type stationary phases, ligand exchange, crown ethers, proteins, polysaccharides, cyclodextrin, and cyclofructan have been developed . In a previous study, a new (R)‐phenylglycinol‐derived C3‐symmetric CSP and three C2‐symmetric CSPs were prepared and their chiral separation performances for 25 chiral samples were evaluated and compared with that of N ‐3,5‐dintrobenzoyl (DNB)‐(R)‐phenylglycinol‐derived CSP, which was previously reported as a brush/Pirkle‐type CSP, under the same separation conditions .…”

Synthesis and Application of C2 and C3 Symmetric (R)‐Phenylglycinol‐Derived Chiral Stationary Phases

“…Various types of high‐performance liquid chromatography (HPLC) chiral stationary phases (CSPs) such as brush/Pirkle‐type stationary phases, crown ethers, ligand exchange, proteins, polysaccharides, cyclodextrin, and cyclofructan have been developed . Many amino acid‐based CSPs have been reported as chiral selectors; for example, (S)‐leucine and (R)‐phenylglycine‐derived brush/Pirkle‐type CSP, (S)‐proline‐ and (S)‐lysine‐derived ligand‐exchange CSPs, and a protein CSP .…”