UPR 5301

Electrospun Cellulosic Membranes toward Efficient Chiral Resolutions via Enantioselective Permeation

13 July 2021

Many biologically-active compounds, such as drugs, agrochemicals, food additives, etc. have chiral structures (like right- and left-hands) and their physiological properties usually depend on their chirality. In this study, cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC), known as one of the most versatile chiral selectors packed in columns for chiral chromatography, is electrospun for the first time to fabricate an enantioselective membrane toward efficient chiral resolutions. We believe that such a novel electrospun cellulosic membrane having both the enantioselective permeation property and the capacity to be used in pressure-driven filtration processes is a significant step forward toward large-scale chiral resolutions. Click on the title for more information.

Abstract:
“Cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC), known as one of the most versatile chiral selectors packed in columns for chiral chromatography, is electrospun for the first time. The electrospun nanofibers with a mean diameter of 329 nm form a self-standing nonwoven textile with a specific surface area of 5.6 m²/g. The textile is sandwiched between commercially available polytetrafluoroethylene membrane filters as a support material to fabricate a CDMPC membrane system for the chiral resolution of a racemic mixture, (R,S)-1-(1-naphthyl)ethanol. A vacuum filtration of the racemic mixture through the membrane system using a mixed solvent of n-hexane/2-propanol = 9/1 (v/v) enriches the S-enantiomer in the filtrate due to an enantioselective sorption of the R-enantiomer. The sorption capacity can be regenerated repeatedly via extractions of the adsorbed enantiomers from the membrane system after the filtrations. By repeating the vacuum filtration–extraction process for 15 cycles, the enantiomeric excess (e.e.) of the S-isomer in the filtrate increases up to 32.9%.”

The article is available over here.