Chirality is a fundamental feature involved in the majority of biological processes. While it can be rather readily observed on the microscopic or molecular level, enantioselective interactions on the macroscopic level are not as well understood. We chemically synthesized L-cellulose, the mirror image and enantiomer of native cellulose, with chains of different chain lengths by polymerizing an L-glucose-derived 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. Across all analytes examined, we observed a complete inversion of the elution order of (R) and (S) enantiomers, consistent with reversed interaction strengths with the stationary phase. These findings advance the understanding of enantioselective recognition from the molecular to the supramolecular scale and underscore the importance of hierarchical chirality in cellulose-based separation media.

Anna Lehrhofer

Universitat fur Bodenkultur Wien

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