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

ACS applied materials & interfaces(2023)

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摘要
Metal-organic frameworks (MOFs) have become promisingmaterialsfor multiple applications due to their controlled dimensionality andtunable properties. The incorporation of chirality into their frameworksopens new strategies for chiral separation, a key technology in thepharmaceutical industry as each enantiomer of a racemic drug mustbe isolated. Here, we describe the use of a combination of computationalmodeling and experiments to demonstrate that high-performance liquidchromatography (HPLC) columns packed with TAMOF-1 asthe chiral stationary phase are efficient, versatile, robust, andreusable 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 differentmolecular sizes, geometries, and functional groups. Initial in silico studies allowed us to predict plausible separationsin chiral compounds from different families, including terpenes, calciumchannel blockers, or P-stereogenic compounds. Theexperimental data confirmed the validity of the models and the robustperformance of TAMOF-1 columns. The added value of in silico screening is an unprecedented achievement in chiralchromatography.
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关键词
metal-organic framework,tight binding,molecular simulation,chiral stationary phase,chiral separations,computationally predictable,HPLC
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