A novel chiral polyester composite membrane: Preparation, enantioseparation of chiral drugs and molecular modeling evaluation

Abstract

Chiral polyester composite membranes were fabricated by covalently bonding cyclodextrins with the commercial cellulose acetate membranes (CAM) using trimesoyl chloride (TMC) as cross-linking agent. β-cyclodextrin (β-CD) and its derivative (Hydroxypropyl-β-cyclodextrin, HP-β-CD) were employed as chiral selectors. Enantiomeric resolution and SEM result confirmed the successful chemical modification of CAM. The effect of modification conditions (e.g. reaction temperature, solution concentration of TMC and organic additives) on the enantioseparation of membranes modified using interfacial polymerization method was then studied by using (DL)-tryptophan ((DL)-Trp) as model chiral drug. Under optimal preparation conditions, enantiomeric excess value (ee) of 7.01 ± 0.41% toward (RS)-warfarin and (ee) of 6.74 ± 1.00% toward (RS)-nefopam were achieved. In addition, the mechanism of chiral recognition was demonstrated using molecular modeling with AutoDock.