TAMOF‑1 as a Versatile and Predictable Chiral Stationary Phase for the Resolution of Racemic Mixtures
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...
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| Published in | ACS applied materials & interfaces Vol. 15; no. 33; pp. 39594 - 39605 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
23.08.2023
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1944-8244 1944-8252 1944-8252 |
| DOI | 10.1021/acsami.3c08843 |
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| 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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| AbstractList | 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. 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.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. 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 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 HPLC columns of nine racemic mixtures with different molecular sizes, geometries, and functional groups. Initial studies allowed us to predict plausible separations in chiral compounds from different families, including terpenes, calcium channel blockers, or -stereogenic compounds. The experimental data confirmed the validity of the models and the robust performance of columns. The added value of screening is an unprecedented achievement in chiral chromatography. |
| Author | Calero, Sofía Núñez-Rico, José Luis Balestra, Salvador R. G. Lillo, Vanesa Vidal-Ferran, Anton Cabezas-Giménez, Juanjo Galán-Mascarós, José Ramón |
| AuthorAffiliation | Institute of Chemical Research of Catalonia (ICIQ-CERCA) and the Barcelona Institute of Science and Technology (BIST) Universitat Rovira i Virgili (URV) Materials Simulation and Modelling, Department of Applied Physics Departamento de Sistemas Físicos, Químicos y Naturales Universitat de Barcelona (UB) Department of Inorganic and Organic Chemistry and the Institute of Nanoscience and Nanotechnology (IN Materials Science Institute of Madrid Spanish National Research Council (ICMM-CSIC) Department of Physical and Inorganic Chemistry UB Eindhoven University of Technology |
| AuthorAffiliation_xml | – name: Department of Inorganic and Organic Chemistry and the Institute of Nanoscience and Nanotechnology (IN – name: Universitat de Barcelona (UB) – name: Materials Science Institute of Madrid – name: Institute of Chemical Research of Catalonia (ICIQ-CERCA) and the Barcelona Institute of Science and Technology (BIST) – name: Department of Physical and Inorganic Chemistry – name: Spanish National Research Council (ICMM-CSIC) – name: Universitat Rovira i Virgili (URV) – name: UB – name: Departamento de Sistemas Físicos, Químicos y Naturales – name: Materials Simulation and Modelling, Department of Applied Physics – name: Eindhoven University of Technology |
| Author_xml | – sequence: 1 givenname: José Luis orcidid: 0000-0001-8629-4908 surname: Núñez-Rico fullname: Núñez-Rico, José Luis organization: Universitat de Barcelona (UB) – sequence: 2 givenname: Juanjo orcidid: 0000-0002-8424-7101 surname: Cabezas-Giménez fullname: Cabezas-Giménez, Juanjo organization: Universitat Rovira i Virgili (URV) – sequence: 3 givenname: Vanesa surname: Lillo fullname: Lillo, Vanesa organization: Institute of Chemical Research of Catalonia (ICIQ-CERCA) and the Barcelona Institute of Science and Technology (BIST) – sequence: 4 givenname: Salvador R. G. orcidid: 0000-0002-2163-2782 surname: Balestra fullname: Balestra, Salvador R. G. organization: Departamento de Sistemas Físicos, Químicos y Naturales – sequence: 5 givenname: José Ramón orcidid: 0000-0001-7983-9762 surname: Galán-Mascarós fullname: Galán-Mascarós, José Ramón email: jrgalan@iciq.es organization: Institute of Chemical Research of Catalonia (ICIQ-CERCA) and the Barcelona Institute of Science and Technology (BIST) – sequence: 6 givenname: Sofía orcidid: 0000-0001-9535-057X surname: Calero fullname: Calero, Sofía email: S.Calero@tue.nl organization: Eindhoven University of Technology – sequence: 7 givenname: Anton orcidid: 0000-0001-7926-1876 surname: Vidal-Ferran fullname: Vidal-Ferran, Anton email: anton.vidal@icrea.cat organization: Universitat de Barcelona (UB) |
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| Snippet | Metal–organic frameworks (MOFs) have become promising materials for multiple applications due to their controlled dimensionality and tunable properties. The... Metal-organic frameworks (MOFs) have become promising materials for multiple applications due to their controlled dimensionality and tunable properties. The... |
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| StartPage | 39594 |
| SubjectTerms | calcium channels computer simulation drugs enantiomers Functional Inorganic Materials and Devices high performance liquid chromatography optical isomerism pharmaceutical industry terpenoids |
| Title | TAMOF‑1 as a Versatile and Predictable Chiral Stationary Phase for the Resolution of Racemic Mixtures |
| URI | http://dx.doi.org/10.1021/acsami.3c08843 https://www.ncbi.nlm.nih.gov/pubmed/37579193 https://www.proquest.com/docview/2851142615 https://www.proquest.com/docview/3040366545 |
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