Elution revolution: Reversing chiral recognition by swapping d- for l-cellulose

Chirality is a fundamental feature involved in most biological processes. While it can be rather readily observed on the molecular or microscopic level, enantioselective interactions on the macroscopic level are not as well understood. We chemically synthesized l-cellulose, the enantiomer of native cellulose with chains of different length by polymerizing an l-glucose-based precursor. A sufficiently high degree of polymerization was crucial for the successful application of this material as a chiral selector. After derivatization, coating onto silica, and packing into columns, the functionalized material was tested in a chiral high-performance liquid chromatography setup to investigate the enantioselective interplay between the modified cellulose mirror images and chiral molecules. We report the first-ever application of synthetic l-cellulose instead of the common column materials based on the natural d-polysaccharide counterparts. An inversion of the analyte elution order of (R) and (S) enantiomers due to reversed interaction strength with the stationary phase was observed for all tested analytes.