Click regulation of cyclodextrin primary face for the preparation of novel chiral stationary phases

Abstract

In this study, a series of novel CD chiral stationary phases were fabricated by immobilization of mono‐6A‐deoxy‐N3‐cyclodextrin onto silica surfaces followed by click regulation of CD primary face with 4‐pentynoic acid (acidic moiety), 2‐propynylamine (alkaline moiety) and L‐propargylglycine (chiral amino acid moiety), respectively. Enantioseparations of various kinds of racemates including dansyl‐amino acids, chiral lactides and diketones were conducted in reversed phase modes on these chiral stationary phases, where nearly forty diketones and chiral lactides were firstly separated on cyclodextrin stationary phases. 4‐Pentynoic acid moiety can make the retention ability decline while amine moiety significantly enhanced the retention ability of the stationary phases. For most of the studied analytes, the chiral amino acid moiety had the most positive effects on both the retention time and the resolution. The inclusion complexation between chiral analytes and cyclodextrins were also investigated by fluorescence method.

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

“…In 2019, Wang and coworkers prepared three mono-6-deoxy-N 3 -CD derivatives by click anchoring of L-propargylglycine, 4-pentynoic acid, or 2-propynylamine at the C-6 position. The derivatives were immobilized on silica as CSPs for HPLC separation of various racemates including dansyl-amino acids, chiral lactides, and diketones [54]. Approximately 40 racemic compounds were first resolved on these CD-based-CSPs, demonstrating the importance of their derivatization on chiral separation.…”