A chiral metal-organic framework {(HQA)(ZnCl2)(2.5H2O)}n for the enantioseparation of chiral amino acids and drugs

被引:17
|
作者
Zheng, Xiangtai [1 ,3 ]
Zhang, Qi [2 ]
Ma, Qianjie [1 ]
Li, Xinyu [1 ]
Zhao, Liang [3 ,4 ]
Sun, Xiaodong [1 ]
机构
[1] Shanghai Univ, Shanghai Engn Res Ctr Organ Repair, Sch Med, Shanghai 200444, Peoples R China
[2] Jiangsu Univ, Sch Pharm, Zhenjiang 212013, Jiangsu, Peoples R China
[3] Shanghai Baoshan Luodian Hosp, Dept Pharm, Shanghai 201908, Peoples R China
[4] Shanghai Univ, Inst Translat Med Res, Luodian Clin Drug Res Ctr, Shanghai 200444, Peoples R China
基金
中国国家自然科学基金;
关键词
Capillary electrochromatography; Metal-organic framework; Enantioseparation; Chiral stationary phase; Open-tubular column; Dansyl amino acids; STATIONARY-PHASE; DERIVATIVES; SEPARATION; POLYMER; PROTEIN; QUININE;
D O I
10.1016/j.jpha.2023.03.003
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Chiral metal-organic frameworks (CMOFs) with enantiomeric subunits have been employed in chiral chemistry. In this study, a CMOF formed from 6-methoxyl-(8S,9R)-cinchonan-9-ol-3-carboxylic acid (HQA) and ZnCl2, {(HQA)(ZnCl2)(2.5H2O)}n, was constructed as a chiral stationary phase (CSP) via an in situ fabrication approach and used for chiral amino acid and drug analyses for the first time. The {(HQA)(ZnCl2)(2.5H2O)}n nanocrystal and the corresponding chiral stationary phase were systematically characterised using a series of analytical techniques including scanning electron microscopy, X-ray diffraction, Fourier transform infrared spectroscopy, circular dichroism, X-ray photoelectron spectros-copy, thermogravimetric analysis, and Brunauer-Emmett-Teller surface area measurements. In open-tubular capillary electrochromatography (CEC), the novel chiral column exhibited strong and broad enantioselectivity toward a variety of chiral analytes, including 19 racemic dansyl amino acids and several model chiral drugs (both acidic and basic). The chiral CEC conditions were optimised, and the enantioseparation mechanisms are discussed. This study not only introduces a new high-efficiency member of the MOF-type CSP family but also demonstrates the potential of improving the enantiose-lectivities of traditional chiral recognition reagents by fully using the inherent characteristics of porous organic frameworks.(c) 2023 The Authors. Published by Elsevier B.V. on behalf of Xi'an Jiaotong University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
引用
收藏
页码:421 / 429
页数:9
相关论文
共 50 条
  • [1] A chiral metal-organic framework synthesized by the mixture of chiral and non-chiral organic ligands for enantioseparation of drugs by open-tubular capillary electrochromatography
    Zhang, Min
    Chen, Jiaquan
    Xu, Guangfu
    Yu, Tao
    Du, Yingxiang
    JOURNAL OF CHROMATOGRAPHY A, 2023, 1699
  • [2] Co-crystallization of racemic amino acids with ZnCl2: an investigation of chiral selectivity upon coordination to the metal centre
    Shemchuk, Oleksii
    Grepioni, Fabrizia
    Braga, Dario
    CRYSTENGCOMM, 2020, 22 (34): : 5613 - 5619
  • [3] Asymmetric Catalytic Sulfoxidation with H2O2 using Chiral Copper Metal-Organic Framework Crystals
    Tanaka, Koichi
    Kubo, Kaori
    Iida, Kazuhiro
    Otani, Ken-ichi
    Murase, Takanori
    Yanamoto, Daisuke
    Shiro, Motoo
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (12) : 1055 - 1060
  • [4] Enantioselective recognition of L/D-amino acids in the chiral nanochannels of a metal-organic framework
    Niu, Xiaohui
    Yan, Simeng
    Chen, Jinliang
    Li, Hongxia
    Wang, Kunjie
    ELECTROCHIMICA ACTA, 2022, 405
  • [5] Metal-Organic Framework [Cd(LTP)2]n for Improved Enantioseparations on a Chiral Cyclodextrin Stationary Phase in GC
    Yang, Jiang-rong
    Xie, Sheng-ming
    Zhang, Jun-hui
    Chen, Ling
    Nong, Rui-yu
    Yuan, Li-ming
    JOURNAL OF CHROMATOGRAPHIC SCIENCE, 2016, 54 (09) : 1467 - 1474
  • [6] Chiral Metal-organic Framework { [ Co(L-trp) (bpe) (H2O) ] • H2O • NO3 } n Used for High Performance Liquid Chromatographic Separation
    Nong Ruiyu
    Kong Jiao
    Zhang Junhui
    Chen Ling
    Tang Bo
    Xie Shengming
    Yuan Liming
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2016, 37 (01): : 19 - 25
  • [7] Chiral Lanthanum Metal-Organic Framework with Gated CO2 Sorption and Concerted Framework Flexibility
    Noa, Francoise M. Amombo
    Grape, Erik Svensson
    Ahlen, Michelle
    Reinholdsson, William E.
    Gob, Christian R.
    Coudert, Francois-Xavier
    Cheung, Ocean
    Inge, A. Ken
    Ohrstrom, Lars
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (19) : 8725 - 8733
  • [8] CELLULOSE ORGANIC-SOLVENTS .2. THE STRUCTURE OF N-METHYLMORPHOLINE N-OXIDE 2.5H2O
    MAIA, E
    PEREZ, S
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1982, 38 (MAR): : 849 - 852
  • [9] Immobilization of cellulase on monolith supported with Zr(IV)-based metal-organic framework as chiral stationary phase for enantioseparation of five basic drugs in capillary electrochromatography
    Mingxuan Ma
    Jian Zhang
    Peipei Li
    Yingxiang Du
    Jie Gan
    Jiangxia Yang
    Liu Zhang
    Microchimica Acta, 2021, 188
  • [10] Immobilization of cellulase on monolith supported with Zr(IV)-based metal-organic framework as chiral stationary phase for enantioseparation of five basic drugs in capillary electrochromatography
    Ma, Mingxuan
    Zhang, Jian
    Li, Peipei
    Du, Yingxiang
    Gan, Jie
    Yang, Jiangxia
    Zhang, Liu
    MICROCHIMICA ACTA, 2021, 188 (06)