Chromatographic stationary phases prepared by taking porous frame material as matrix and used for chiral separation

A porous framework and chiral separation technology, applied in the field of chromatographic chiral separation, can solve problems such as poor stability, easy leakage of chiral resolving agent, and low loading rate of chiral resolving agent

Active Publication Date: 2019-04-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the problems of poor stability, low loading rate of chiral resolving agent and easy leakage of chiral resolving agent in traditional chiral stationary phase carrier materials, this application creatively screens and designs porous framework materials as chiral stationary phase carriers. It has excellent properties such as easy modification, high stability, high specific surface area and porosity, and is loaded with chiral resolving agents (such as proteins, enzymes, macrocyclic antibiotics, etc.) by chemical bonding, adsorption, embedding and other means to prepare High-efficiency chiral stationary phase (CSP) to overcome the application limitations of traditional materials in chiral chromatography columns

Method used

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  • Chromatographic stationary phases prepared by taking porous frame material as matrix and used for chiral separation
  • Chromatographic stationary phases prepared by taking porous frame material as matrix and used for chiral separation
  • Chromatographic stationary phases prepared by taking porous frame material as matrix and used for chiral separation

Examples

Experimental program
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Effect test

Embodiment 1

[0048] The synthesis of the covalent organic framework material COF-1 used for chemically bonding a chiral resolving agent, the specific implementation steps are as follows:

[0049]Weigh the ligands 1,3,5-tris-(4-aminobenzene)triazine (TAPT 0.10 mmol) and pyromellitic dianhydride (PMDA 0.15 mmol) into thick-wall heat-resistant glass tubes (o.d. × i.d = 10 × 8 mm 2 ), then add 0.5 mL of mesitylene, 0.5 mL of N-methylpyrrolidone and 0.05 mL of isoquinoline, and then quickly freeze in liquid nitrogen, then vacuumize, and then seal the tube with a hydrogen oxygen machine flame. The sealed glass tube was placed in an oven at 200° C. for 5 days to obtain COF-1 as a yellow solid product.

[0050] Solvent Activation of Porous Framework Material COF-1

[0051] The obtained solid was washed several times with anhydrous tetrahydrofuran until the supernatant was colorless, and then extracted with 100 mL of anhydrous tetrahydrofuran for 24 hours. The obtained yellow solid was activated ...

Embodiment 2

[0052] Example 2: Chemical bonding of enzymes with covalent organic framework material COF-1 as a carrier

[0053] Activation of carboxylic acids in covalent organic framework material COF-1

[0054] Weigh 10 mg COF-1 into a 20 mL glass reaction vial, then add an equivalent amount of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide and N-hydroxysuccinimide Amine-based 2-morpholineethanesulfonic acid buffer solution (MES) 5 mL, after shaking on a shaker at room temperature for 2 hours, filter COF-1, and then wash 3-5 times with 5 mL 0.1M MES buffer solution of pH 6.0 , and then dried at room temperature.

[0055] Activated COF-1 chemically bonded enzyme

[0056] Weigh 10 mg of activated COF-1, add it to a 20 mL glass reaction vial, then add 2 mL of MES buffer solution containing 3 mg / mL enzyme to the vial, and shake on a shaker at 37 °C. as attached figure 1 At intervals as shown, the ultraviolet absorption of the supernatant was tested to calculate the amount of enzyme loade...

Embodiment 3

[0059] Example 3: Chemical Bonding of Vancomycin Using Covalent Organic Framework Material COF-1 as a Carrier

[0060] Activated COF-1 chemically binds vancomycin

[0061] Weigh 5 mg of activated COF-1, add to a 10 mL centrifuge tube, then add 2 mL of 5 mg / mL vancomycin aqueous solution to the centrifuge tube, and shake on a shaker at 37 °C. as attached image 3 At intervals as shown, the ultraviolet absorption of the supernatant was tested to calculate the amount of vancomycin loaded on the material, and the chemical bond immobilization curve of COF-1 to vancomycin was drawn.

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Abstract

The invention discloses chromatographic stationary phases prepared by taking a porous frame material as a matrix and used for chiral separation study. Aiming at the problem that carrier materials of conventional chiral chromatographic column stationary phases may be poor in stability, low in chiral resolving agent loading rate, prone to chiral resolving agent loss and limited in suitability, the porous frame material (like metal organic frame materials and covalent organic frame materials) is creatively designed and developed to serve as a novel carrier material having extensive suitability, and chiral resolving agents (protein, enzyme and macrocyclic antibiotics) are efficiently loaded by means of covalence, adsorption, embedding and crosslinking so as to prepare various efficient and durable chiral stationary phases to serve as novel high-performance chromatographic column filler for chromatographic chiral separation (like high-performance liquid phase chromatography and capillary chromatography). The chiral stationary phases prepared by using the technology has high separation efficiency and high stability and durability and can be successfully applied in efficient separation ofvarious chiral substances like chiral amini acid and chiral drug. The technology greatly widens application range and prolongs service life of chiral chromatographic column separation.

Description

technical field [0001] The invention belongs to the field of chromatographic chiral separation, and specifically relates to a variety of chromatographic separation methods suitable for high performance liquid chromatography (HPLC), gas chromatography (GC), capillary electrophoresis (CE), etc. The biomolecule of the chiral unit is the preparation of the composite novel chiral stationary phase of the chiral resolving agent. The patent claim cites the priority of the following Chinese invention patent, application number 201810027487.0, application date January 11, 2018. Background technique [0002] Chirality is ubiquitous in nature, such as biological macromolecules that constitute living organisms, including proteins, nucleic acids, enzymes, etc., as well as many drugs and foods, all have a single chiral structure. Chiral compounds generally have two enantiomers, which are almost identical in physical and chemical properties, but there are significant differences in the bio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01D15/38
CPCB01D15/3833B01J20/226B01J20/3206B01J20/3217B01J20/24B01J20/2808B01J20/28083B01J20/3274B01J20/29B01J2220/52
Inventor 陈瑶张振杰张赛男
Owner NANKAI UNIV
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