Homochiral Metal-Organic Frameworks for Enantioselective Separations in Liquid Chromatography

被引:102
|
作者
Corella-Ochoa, Nieves [1 ]
Tapia, Jesus B. [2 ]
Rubin, Heather N. [2 ]
Lillo, Vanesa [1 ]
Gonzalez-Cobos, Jesus [1 ]
Luis Nunez-Rico, Jose [1 ]
Balestra, Salvador R. G. [4 ]
Almora-Barrios, Neyvis [5 ]
Lledos, Marina [1 ]
Guell-Bara, Arnau [1 ]
Cabezas-Gimenez, Juanjo [1 ,8 ]
Escudero-Adan, Eduardo C. [1 ]
Vidal-Ferran, Anton [1 ,6 ]
Calero, Sofia [4 ,7 ]
Reynolds, Melissa [2 ,3 ]
Marti-Gastaldo, Carlos [5 ]
Ramon Galan-Mascaros, Jose [1 ,6 ]
机构
[1] BIST, ICIQ, Av Paisos Catalans 16, E-43007 Tarragona, Spain
[2] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[3] Colorado State Univ, Sch Biomed Engn, Ft Collins, CO 80523 USA
[4] Univ Pablo de Olavide, Dept Phys Chem & Nat Syst, Ctra Utrera Km 1, Seville 41013, Spain
[5] Univ Valencia, Inst Ciencia Mol, Calle Catedra Jose Beltran 2, Paterna 46980, Spain
[6] ICREA, Passeig Lluis Co 23, E-08010 Barcelona, Spain
[7] Eindhoven Univ Technol, Dept Appl Phys, NL-5600 MB Eindhoven, Netherlands
[8] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, Marcelli Domingo S-N, E-43007 Tarragona, Spain
基金
美国国家科学基金会;
关键词
POROUS MATERIALS; FORCE-FIELD; HYDROCARBON SEPARATIONS; ADSORPTION; WATER; SELECTIVITY; MEMBRANE; SITES; FLEXIBILITY; CHEMISTRY;
D O I
10.1021/jacs.9b06500
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Selective separation of enantiomers is a substantial challenge for the pharmaceutical industry. Chromatography on chiral stationary phases is the standard method, but at a very high cost for industrial-scale purification due to the high cost of the chiral stationary phases. Typically, these materials are poorly robust, expensive to manufacture, and often too specific for a single desired substrate, lacking desirable versatility across different chiral analytes. Here, we disclose a porous, robust homochiral metal-organic framework (MOF), TAMOF-1, built from copper(II) and an affordable linker prepared from natural L-histidine. TAMOF-1 has shown to be able to separate a variety of model racemic mixtures, including drugs, in a wide range of solvents of different polarity, outperforming several commercial chiral columns for HPLC separations. Although not exploited in the present article, it is worthy to mention that the preparation of this new material is scalable to the multikilogram scale, opening unprecedented possibilities for low-energy chiral separation at the industrial scale.
引用
收藏
页码:14306 / 14316
页数:11
相关论文
共 50 条
  • [31] Homochiral Tetraphenylethene-Based Metal-Organic Frameworks with Circularly Polarized Luminescence for Enantioselective Recognition
    Zhou, Ying-Ying
    Ying, Yan-Mei
    Jiang, Mei-Zhu
    Dai, Han-Xiao
    Zhao, Zujin
    Liu, Xun-Gao
    [J]. INORGANIC CHEMISTRY, 2024, 63 (25) : 11566 - 11571
  • [32] Homochiral Metal-Organic Frameworks for Heterogeneous Asymmetric Catalysis
    Dang, Dongbin
    Wu, Pengyan
    He, Cheng
    Xie, Zhong
    Duan, Chunying
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) : 14321 - 14323
  • [33] Homochiral helical metal-organic frameworks of group 1
    Leitner, Andrew
    Reger, Daniel
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [34] Homochiral porous metal-organic frameworks: Why and how?
    Lin, WB
    [J]. JOURNAL OF SOLID STATE CHEMISTRY, 2005, 178 (08) : 2486 - 2490
  • [35] Chiral templated synthesis of homochiral metal-organic frameworks
    Berijani, Kayhaneh
    Chang, Li-Mei
    Gu, Zhi-Gang
    [J]. COORDINATION CHEMISTRY REVIEWS, 2023, 474
  • [36] Homochiral Metal-Organic Frameworks for Asymmetric Heterogeneous Catalysis
    Yoon, Minyoung
    Srirambalaji, Renganathan
    Kim, Kimoon
    [J]. CHEMICAL REVIEWS, 2012, 112 (02) : 1196 - 1231
  • [37] Liquid metal-organic frameworks
    Gaillac, Romain
    Pullumbi, Pluton
    Beyer, Kevin A.
    Chapman, Karena W.
    Keen, David A.
    Bennett, Thomas D.
    Coudert, Francois-Xavier
    [J]. NATURE MATERIALS, 2017, 16 (11) : 1149 - +
  • [38] A homochiral metal-organic porous material for enantioselective separation and catalysis
    Seo, JS
    Whang, D
    Lee, H
    Jun, SI
    Oh, J
    Jeon, YJ
    Kim, K
    [J]. NATURE, 2000, 404 (6781) : 982 - 986
  • [39] A computational study of enantioselective adsorption in a homochiral metal-organic framework
    Bao, Xiaoying
    Broadbelt, Linda J.
    Snurr, Randall Q.
    [J]. MOLECULAR SIMULATION, 2009, 35 (1-2) : 50 - 59
  • [40] Enantioselective adsorption in zeolites and metal-organic frameworks
    Bueno-Perez, Rocio
    Martin-Calvo, Ana
    Gomez-Alvarez, Paula
    Gutierrez-Sevillano, Juan-Jose
    Merkling, Patrick
    Vlugt, Thijs
    van Erp, Titus S.
    Dubbeldam, David
    Calero, Sofia
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249