journal article·2023-08-23Open access

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

José Luis Núñez-Rico, Juanjo Cabezas-Giménez, Vanesa Lillo, Salvador R. G. Balestra, José Ramón Galán-Mascarós, Sofía Calero, Anton Vidal-Ferran

ACS Applied Materials & Interfaces· Volume 15· Issue 33

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.
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Research context

OpenAlex topics: Metal-Organic Frameworks: Synthesis and Applications · Analytical Chemistry and Chromatography · Crystallography and molecular interactions

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Institute of Chemical Research of Catalonia (ICIQ-CERCA) and the Barcelona Institute of Science and Technology (BIST), Av. Països Catalans 16, 43007 Tarragona, Spain

Department of Inorganic and Organic Chemistry and the Institute of Nanoscience and Nanotechnology (IN2UB), Universitat de Barcelona (UB), C/Martí i Franqués 1-11, 08028 Barcelona, Spain

Department of Physical and Inorganic Chemistry, Universitat Rovira i Virgili (URV), C/Marcel lí Domingo s/n, 43007 Tarragona, Spain

Materials Science Institute of Madrid, Spanish National Research Council (ICMM-CSIC), C/Sor Juana Inés de la Cruz, 3, 28049 Madrid, Spain

Departamento de Sistemas Físicos, Químicos y Naturales, Universidad Pablo de Olavide, Ctra. Utrera km 1, 41013 Seville, Spain

Catalan Institution for Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona, Spain

Materials Simulation and Modelling, Department of Applied Physics, Eindhoven University of Technology, 5600 MB Eindhoven, The Netherlands

Funding

Ministerio de Ciencia e Innovación · Generalitat de Catalunya · Agencia Andaluza de Conocimiento, Secretaría General de Universidades, Investigación y Tecnología

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