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Preparation method and application of mimic enzyme MOF-based chiral separation material

A chiral separation and enzyme imitation technology, which is applied in the field of material chemistry and chiral chemistry, can solve the problems of expensive chiral ligands, and achieve the effects of wide separation of substrates, mild synthesis conditions and excellent selectivity

Active Publication Date: 2020-09-04
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is that the chiral ligands used in MOF-based chiral separation materials in the prior art are expensive and require multi-step synthesis, and a method for preparing enzyme-like MOF-based chiral separation materials is provided

Method used

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  • Preparation method and application of mimic enzyme MOF-based chiral separation material
  • Preparation method and application of mimic enzyme MOF-based chiral separation material
  • Preparation method and application of mimic enzyme MOF-based chiral separation material

Examples

Experimental program
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Embodiment 1

[0058] The preparation of enzyme-like MOF-based chiral separation materials, the reaction formula is as follows:

[0059]

[0060] The enzyme-like MOF-based chiral separation material is named compound 1. The above reaction formula is the smallest asymmetric unit of the crystal structure of compound 1, and its crystal structure is the periodic infinite extension structure of the asymmetric unit.

[0061] Zinc acetate dihydrate (18.3 mg, 0.10 mmol), monochiral ligand H 2 L (23mg, 0.05mmol) and auxiliary ligand bpy (7.8mg, 0.05mmol) were dissolved in N,N-dimethylacetamide (DMA), ethanol (EtOH) and water ( h 2 O) in the mixed solvent, the volume ratio of N,N-dimethylacetamide, ethanol and water is 1:1:1, stir evenly, and seal the resulting reaction liquid mixture in a 10mL explosion-proof vial. h 2 L is 2'2-(terephthaloyl bis(azadiyl)) bis(3-phenylpropionic acid), ligand H in the present embodiment 2 L is the existing technology, using Yu S L, Dou X Q, Qu D H, etal. -98. ...

Embodiment 2

[0064] Single crystal test and structural analysis of compound 1

[0065] The single crystal data of compound 1 is in the National Center for Protein Science Shanghai Synchrotron Radiation BL17B Multiple collections were carried out on the online station, and the optimal data were indexed, restored, and absorbed and corrected with the APEX3 software program. The final structure analysis and refinement were done manually through the SHELXS-97 program, during which the full-matrix least-squares refinement based on F 2 ) to determine all non-hydrogen atoms and perform anisotropic refinement. In addition, the hydrogen atoms on the ligand are completed by theoretical hydrogenation

[0066] Such as Figure 1-Figure 4 As shown, single crystal diffraction data analysis showed that compound 1 crystallized in the chiral P32 1 Space group whose asymmetric unit content is its molecular formula [(Zn 4 O) 2 (L) 6 (bpy) 3 ], which contains 2 crystallographically independent Zn i...

Embodiment 3

[0070] The application of enzyme-like MOF-based chiral separation materials in the adsorption and separation of small molecular aromatic alcohols, the specific steps are as follows:

[0071] (1) Activation treatment: the crystal of compound 1 prepared in Example 1 was placed in a Soxhlet extractor, treated with anhydrous methanol for 24 hours, then treated with anhydrous acetone for 24 hours, and then activated in vacuum at 100°C to remove organic solvent;

[0072] (2) 50 mg of the crystal of compound 1 after the activation treatment was placed in a solution of racemic aromatic alcohol small molecule substrate (10 mg) in acetone (5 mL) to be resolved and allowed to stand for 5 h to allow the substrate to be fully adsorbed ; The above-mentioned crystals after fully adsorbing the chiral alcohol small molecule substrate are filtered, the racemic chiral alcohol small molecule substrate adhered to the surface of the compound 1 crystal is washed away with methanol, and the crystal o...

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Abstract

The invention discloses a preparation method of an enzyme-mimic MOF-based chiral separation material. The preparation method comprises the steps: using optically pure ligand 2 '2-(paraphthaloyl bis (azadiyl)) bis (3-phenylpropionic acid), 4, 4'-dipyridyl and zinc ions as raw materials, and forming a crystal MOF material containing amphiphilic chiral nanochannels through coordination. The inventionalso provides the mimic enzyme MOF-based chiral separation material prepared by the preparation method and application thereof. The beneficial effects of the method are that: a simple chiral ligand containing peptide bonds is selected as a chiral source to synthesize the MOF-based separation material, the synthesis cost and difficulty are reduced; particularly, the prepared chiral MOF has a simulated biological enzyme multiple recognition site and a unique chiral microenvironment, and can be used as a recyclable chiral solid-phase separation material for high-enantioselectivity resolution ofracemic aromatic alcohols, epoxy compounds, ibuprofen and other small-molecular chiral compounds.

Description

technical field [0001] The invention relates to the fields of material chemistry and chiral chemistry, in particular to a preparation method and application of an enzyme-like MOF-based chiral separation material. Background technique [0002] Chirality refers to the phenomenon that a substance and its mirror image cannot overlap. Just like the left hand and right hand of a person, they cannot overlap each other through any operation. There are chiral phenomena ranging from molecules and atoms in the microscopic world to macroscopic substances in nature. Therefore, chirality It is one of the most important properties of substances in nature. Chirality not only affects the physical and chemical properties of substances, but is also closely related to life phenomena. Chiral compounds, especially the two mirror-image enantiomers of chiral drugs, often exhibit distinct pharmacological, toxicological, and pharmacokinetic activities in organisms. Therefore, the development of chi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00B01J20/29B01J20/30B01D15/38
CPCC08G83/008B01J20/29B01D15/3833
Inventor 朱成峰杨可可王洪朝张阿美吴祥李有桂
Owner HEFEI UNIV OF TECH
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