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

被引:5
|
作者
Nunez-Rico, Jose Luis [1 ,2 ,3 ,4 ]
Cabezas-Gimenez, Juanjo [1 ,2 ,5 ]
Lillo, Vanesa [1 ,2 ]
Balestra, Salvador R. G. [6 ,7 ]
Galan-Mascaros, Jose Ramoon [1 ,2 ,8 ]
Calero, Sofia [9 ]
Vidal-Ferran, Anton [3 ,4 ,8 ]
机构
[1] Inst Chem Res Catalonia ICIQ CERCA, Tarragona 43007, Spain
[2] Barcelona Inst Sci & Technol BIST, Tarragona 43007, Spain
[3] Univ Barcelona UB, Dept Inorgan & Organ Chem, Barcelona 08028, Spain
[4] Univ Barcelona UB, Inst Nanosci & Nanotechnol IN2UB, Barcelona 08028, Spain
[5] Univ Rovira & Virgili URV, Dept Phys & Inorgan Chem, Tarragona 43007, Spain
[6] Spanish Natl Res Council ICMM CSIC, Mat Sci Inst Madrid, Madrid 28049, Spain
[7] Univ Pablo Olavide, Dept Sistemas Fis Quim & Nat, Seville 41013, Spain
[8] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain
[9] Eindhoven Univ Technol, Dept Appl Phys, Mat Simulat & Modelling, NL-5600 MB Eindhoven, Netherlands
关键词
metal-organic framework; tight binding; molecular simulation; chiral stationary phase; chiral separations; computationally predictable; HPLC; METAL-ORGANIC FRAMEWORKS; ENANTIOSELECTIVE ADSORPTION; CHROMATOGRAPHIC RESOLUTION; ENANTIOMERIC SEPARATION; CALCIUM-ANTAGONIST; HOMOCHIRAL MOF; ESSENTIAL OILS; HPLC; PERFORMANCE; INHIBITORS;
D O I
10.1021/acsami.3c08843
中图分类号
TB3 [工程材料学];
学科分类号
0805 ; 080502 ;
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.
引用
收藏
页码:39594 / 39605
页数:12
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