Chiral stationary phases based on lactide derivatives for high-performance liquid chromatography

•Chiral stationary phases (CSPs) based on lactide were prepared for the first time.•The recognition ability of lactide CSPs can be regulated by ammonolysis.•It demonstrates that lactide derivatives can provide a platform for novel CSPs. Lactide is a natural and renewable lactone cyclic ester-contain...

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Bibliographic Details
Published in:Journal of Chromatography A 2022-01, Vol.1661, p.462705, Article 462705
Main Authors: Pei, Yuanyuan, Li, Xinyu, Zeng, Guangjian, Gao, Yuting, Wen, Tao
Format: Article
Language:English
Subjects:
Chiral recognition
Chiral stationary phase
High-performance liquid chromatography
Lactide
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Summary:•Chiral stationary phases (CSPs) based on lactide were prepared for the first time.•The recognition ability of lactide CSPs can be regulated by ammonolysis.•It demonstrates that lactide derivatives can provide a platform for novel CSPs. Lactide is a natural and renewable lactone cyclic ester-containing intrinsic chiral center, providing an affordable natural compound that is potential for the development of chiral polymers. In this work, we reported two novel chiral stationary phases (CSPs) based on lactide derivatives, methylene lactide (MLA), for high-performance liquid chromatography (HPLC). By using free radical polymerization, chemically bonded CSPs of poly(methylene lactide) (PMLA) and side-chain modified PMLA by aminolysis (N-PMLA) can be prepared. Also, poly(l-lactic acid) (PLLA) was prepared as a control. The chiral resolution performance of the chromatographic columns was examined in both reversed-phase and normal-phase modes. PMLA and N-PMLA CSPs exhibited fairly good chiral recognition ability, whereas the separation ability of PLLA is much weaker. This work provides a new platform for the development of high-performance CSPs from affordable natural products.
ISSN:0021-9673
DOI:10.1016/j.chroma.2021.462705