TAMOF-1 as a Versatile and Predictable Chiral Stationary Phase for the Resolution of Racemic Mixtures

ACS Appl Mater Interfaces. 2023 Aug 23;15(33):39594-39605. doi: 10.1021/acsami.3c08843. Epub 2023 Aug 14.

Abstract

Metal-organic frameworks (MOFs) have become promising materials for multiple applications due to their controlled dimensionality and tunable properties. The incorporation of chirality into their frameworks opens new strategies for chiral separation, a key technology in the pharmaceutical industry as each enantiomer of a racemic drug must be isolated. Here, we describe the use of a combination of computational modeling and experiments to demonstrate that high-performance liquid chromatography (HPLC) columns packed with TAMOF-1 as the chiral stationary phase are efficient, versatile, robust, and reusable with a wide array of mobile phases (polar and non-polar). As proof of concept, in this article, we report the resolution with TAMOF-1 HPLC columns of nine racemic mixtures with different molecular sizes, geometries, and functional groups. Initial in silico studies allowed us to predict plausible separations in chiral compounds from different families, including terpenes, calcium channel blockers, or P-stereogenic compounds. The experimental data confirmed the validity of the models and the robust performance of TAMOF-1 columns. The added value of in silico screening is an unprecedented achievement in chiral chromatography.

Keywords: HPLC; chiral separations; chiral stationary phase; computationally predictable; metal−organic framework; molecular simulation; tight binding.