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

Area of Science:

• Polymer Chemistry
• Analytical Chemistry
• Chiral Separations

Background:

• Lactide is a renewable, affordable cyclic ester with an intrinsic chiral center, making it suitable for developing chiral polymers.
• Chiral stationary phases (CSPs) are crucial for enantiomeric separation in high-performance liquid chromatography (HPLC).
• Developing cost-effective and efficient CSPs from natural products remains an active area of research.

Purpose of the Study:

• To synthesize and characterize novel chiral stationary phases (CSPs) derived from methylene lactide (MLA).
• To evaluate the chiral resolution performance of these new CSPs using HPLC in both reversed-phase and normal-phase modes.
• To explore the potential of lactide derivatives as a sustainable platform for high-performance CSP development.

Main Methods:

• Synthesis of poly(methylene lactide) (PMLA) and side-chain modified N-PMLA CSPs via free radical polymerization and aminolysis.
• Preparation of poly(l-lactic acid) (PLLA) as a control CSP.
• Chiral resolution analysis using HPLC in reversed-phase and normal-phase chromatography.

Main Results:

• PMLA and N-PMLA CSPs demonstrated significant chiral recognition ability in HPLC separations.
• The PLLA control CSP exhibited much weaker separation capabilities compared to PMLA and N-PMLA.
• Both reversed-phase and normal-phase modes were effective in evaluating the chiral resolution performance.

Conclusions:

• Novel CSPs based on PMLA and N-PMLA derived from lactide show promising chiral separation performance.
• Lactide derivatives offer a viable and affordable natural product platform for developing advanced CSPs.
• These findings contribute to the development of sustainable materials for chiral chromatography.