Maltodextrin-starch chiral composite membranes: Preparation, enantioselective recognition of phenylalanine and ibuprofen enantiomers, and molecular docking simulation

The growing demand for single enantiomers has led to rapid advancements in chiral separation methods. Membrane separation , known for its simplicity in preparation, energy efficiency, sustainable operation, and scalability, shows great promise for large-scale separation of enantiomers . However, traditional chiral membranes face challenges in balancing permeability and enantioselectivity . Dextrins , like maltodextrins (MDs), which possess intrinsic chirality , offer a potential solution. In this study, novel chiral composite membranes were developed by combining MDs and its derivatives (carboxymethylated MD (CMMD) and hydroxypropylated MD (HPMD)) with retrograde starch (ST) using cellulose triacetate (CTA) as a matrix material for enantioseparation of chiral amino acid and drug. Optimization of fabrication parameters and enantioseparation conditions was conducted to enhance the separation efficiency of the membranes. The MD-ST/CTA, CMMD-ST/CTA, and HPMD-ST/CTA chiral composite membranes exhibited e.e.% values of 88.0 %, 98.2 %, and 93.6 % for phenylalanine , and 18.8 %, 23.6 %, and 20.1 % for racemic ibuprofen , respectively. These membranes also demonstrated high permeability (233 mmol m⁻ 2 h⁻ 1 for phenylalanine and 142 mmol m⁻ 2 h⁻ 1 for ibuprofen), along with acceptable chemical and mechanical resistance. Molecular docking simulation elucidated the separation mechanism of chiral molecules, highlighting the role of multiple interactions in promoting enantiomeric separation. These results underscore the exceptional enantioseparation performance of the developed chiral composite membranes, offering new insights into their design. • Maltodextrin-starch chiral membranes were developed by simple synthesis procedures. • Modified membranes showed high selectivity for L/ d -phenylalanine and R/S-ibuprofen. • Superior permeability and long-term filtration stability were obtained. • The membranes exhibited suitability for multiple reuses in enantioseparation cycles. • Enantioseparation mechanism was understood through molecular docking simulation.