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Chiral crown ether column capable of effectively splitting amino acid at normal temperature

A technology for amino acids and crown ethers, applied in the field of chromatographic separation columns, can solve problems such as harsh temperature conditions, unfavorable daily applications, and poor chiral resolution of mixed amino acids, achieving low cost and high reproducibility for column preparation Effect

Inactive Publication Date: 2017-07-28
YUNNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the high performance liquid chromatography specially used for the chiral resolution of amino acids has defects such as poor chiral resolution of mixed amino acids, and harsh temperature conditions for chiral resolution of some single amino acids, which is not conducive to daily application.
Therefore, research and development of a new high performance liquid chromatography chiral separation column to realize the effective separation of amino acids under normal temperature conditions has become a technical problem to be solved urgently, but there is no good solution in the prior art.

Method used

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  • Chiral crown ether column capable of effectively splitting amino acid at normal temperature
  • Chiral crown ether column capable of effectively splitting amino acid at normal temperature
  • Chiral crown ether column capable of effectively splitting amino acid at normal temperature

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthetic steps of R‐(3,3'‐chloro‐1,1'‐binaphthyl)‐20‐crown‐6, such as figure 1 Shown:

[0028] in N 2 Under protection, add 150ml acetone to a 500mL round bottom flask, then add 8g R‐binaphthol in turn, add dry and fine potassium carbonate powder K 2 CO 3 (20g, 0.2mol), stirred evenly and heated to 70°C, slowly added iodomethane (5.1mL, 0.10mol) dropwise through a constant pressure funnel, refluxed for 12h and then detected by TCL. , (eluent, acetone:cyclohexane=1:10, with distilled water, with dichloromethane extraction, with anhydrous NaSO 4 The solid was dried and filtered, and the solvent was removed under reduced pressure, and the residue was purified by a silica gel column (eluent, acetone:petroleum ether=1:40) and passed through the column. Obtained white crystal B;

[0029] in N 2 Under protection, dissolve 4g of B into 150mL ether solution, then add 32.1mL of n-butyllithium and 5.6mL of tetramethyldiethylamine, stir at 25°C for 8h, cool the reactant ...

Embodiment 2

[0039] After R‐(3,3'‐dibromo‐1,1'‐binaphthyl)‐20‐crown‐6 chiral stationary phase was used for 240 hours under the above chromatographic experimental conditions, the retention factor K of each α‐amino acid, The separation factor α and resolution Rs remain basically unchanged, indicating that the R-(1,1'-dinaphthyl)-20-crown-6 chiral stationary phase is very stable and can be used for a long time under the above chromatographic conditions .

Embodiment 3

[0041] The mobile phase is the perchloric acid solution of pH=2, V (flow rate)=0.4mL / min, T (column temperature)=25 ℃ of conditions that the detection wavelength is 210nm, the present invention R-(3,3'-dibromo Base‐1,1'‐binaphthyl)‐20‐crown‐6 chiral crown ether column compared with Japanese commercial column CROWNPAKCR(+)CSP, the typical comparison spectrum is as follows image 3 shown. At room temperature, histidine and valine, which cannot be resolved in the commercial column, were separated from the R‐(3,3'‐dibromo‐1,1'‐binaphthyl)‐20‐crown‐6 crown ether column can be effectively resolved, and serine can be better resolved in the chromatographic column of the present invention.

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Abstract

The invention discloses a chiral crown ether column capable of effectively splitting amino acid at normal temperature. Synthesized R-(3, 3'-chlorine-1, 1'-dinaphthyl)-20-crown-6 is prepared into a chiral crown ether stationary phase, and C18 surfaces are coated with crown ether by a physical coating method, so that the high-performance liquid chromatography chiral crown ether column is further prepared. The prepared chiral crown ether has special identification ability for chiral primary amine and can effectively split twenty amino acids under the normal-temperature conditions, and the separating effect of the chiral crown ether column is obviously superior to that of a domestic and international similar high-performance liquid chromatography chiral separation column. The chiral column has the advantages that the column is high in repeatability and relative low in column manufacturing cost, can be repeatedly used and the like.

Description

technical field [0001] The invention belongs to the technical field of chromatographic separation columns, and in particular relates to an R-(3,3'-chloro-1,1'-binaphthyl)-20-crown-6 capable of effectively separating amino acids at normal temperature High performance liquid chromatography chiral crown ether column. Background technique [0002] The study of chiral compounds has now become the most important and active field in the study of stereochemistry, and the resolution of chiral compounds is the basis of chiral compound research. In recent years, the resolution of chiral compounds has made great progress. Especially in terms of chromatographic chiral stationary phases, high performance liquid chromatography has the advantages of high separation efficiency, good selectivity, high detection sensitivity, automatic operation, and wide application range. It is widely used in biochemistry and molecular biology, medicine, agriculture, Environmental protection, commodity insp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01D15/20B01D15/38C07C227/34C07C229/08C07C229/22C07D233/64
CPCB01D15/206B01D15/3833C07C227/34C07D233/64C07C229/08C07C229/22
Inventor 袁黎明吴玉萍谢生明章俊辉
Owner YUNNAN NORMAL UNIV
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