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Chiral probe compound based on square amide skeleton and synthesis of compound and application of fluorescence recognition of amino acid enantiomers

A fluorescence recognition and compound technology, which is applied in the field of chemical synthesis and chiral recognition detection, can solve the problems of long synthetic route, complex structure and high price

Active Publication Date: 2019-03-08
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Most of the chiral fluorescent probe molecules reported in the literature have complex structures, long synthetic routes and high prices

Method used

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  • Chiral probe compound based on square amide skeleton and synthesis of compound and application of fluorescence recognition of amino acid enantiomers
  • Chiral probe compound based on square amide skeleton and synthesis of compound and application of fluorescence recognition of amino acid enantiomers
  • Chiral probe compound based on square amide skeleton and synthesis of compound and application of fluorescence recognition of amino acid enantiomers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1. Synthesis of probe compound a

[0043] (1) Synthesis of intermediate compounds: Add dimethyl squarylate (10.0 mmol) and 10 mL of dry anhydrous methanol into a 50 mL reactor, and stir until the dimethyl squarylate is completely dissolved in methanol. Dissolve p-methylaniline (10.0mmol) in 5ml of methanol and add it dropwise slowly. During the dropwise addition, a yellow substance precipitates. After adding p-methylaniline, stir at room temperature for 10 minutes. Filter and wash with anhydrous methanol several times to obtain a filter residue as a pale yellow solid. After the mother liquor was concentrated by half, it was frozen for 2 h and then filtered again, washed with anhydrous methanol several times to obtain the filter residue. 1.7g of the product was obtained for the first time, and 0.21g of the product was obtained for the second time. A total of 1.91g of the product was obtained, with a yield of 88%. Its synthetic formula is:

[0044]

[0045] (2) Synt...

Embodiment 2

[0056] 1. Synthesis of probe compound b

[0057] (1) Synthesis of intermediate compounds: same as Example 1;

[0058] (2) Synthesis of tert-butyl phenylalanine: Dissolve L-phenylalanine (20.0mmol) in tert-butyl acetate in 100mL, cool in an ice bath, slowly add perchloric acid (30mmol) dropwise under stirring, drop After completion, it was naturally raised to room temperature and stirred for 12 h. The reaction solution was washed with water and 1.0mol / L hydrochloric acid successively, then the pH value was adjusted to 9 with 10% potassium carbonate aqueous solution, extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated, and the obtained crude product was used for The yellow oily substance tert-butyl phenylalanine was separated by column chromatography, and the yield was 69%. Its synthetic formula is as follows:

[0059]

[0060] (3) Synthesis of probe compound b: Add the intermediate compound (1.5mm...

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Abstract

The invention relates to a chiral probe compound based on a square amide skeleton. The method includes, firstly, taking methanol as a solvent, and reacting dimethyl squamate with substituted aniline to prepare an intermediate compound; then taking the methanol as the solvent, reacting the intermediate compound with the amino acid ester for 2-6 hours at room temperature, filtering after the reaction is finished to obtain the probe compound based on the square amide skeleton. In the ethanol-water solution of the probe compound, isomeric enantiomer solutions of phenylalanine, valine and proline are respectively added, and the fluorescence intensity of the probe compound can have different change trends, so the probe compound has a better recognition effect on the two enantiomers of the phenylalanine, the valine and the proline.

Description

technical field [0001] The present invention relates to a chiral probe compound, in particular to a chiral probe compound based on a square amide skeleton; the present invention also relates to the synthesis of the chiral probe compound and the specific application of fluorescence recognition of amino acid enantiomers, belonging to Chemical synthesis technology field and chiral recognition detection technology field. Background technique [0002] Enantiomers have almost identical physical and chemical properties in an achiral environment due to their high structural similarity (only the spatial conformation is different), so the identification, detection and separation of chiral compounds is very challenging. At present, relatively mature detection and separation methods mainly include high performance liquid chromatography, capillary electrophoresis and gas chromatography. However, these methods also have many disadvantages, such as the complexity of the instruments used, ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C227/18C07C229/34G01N21/64
CPCC07C229/34C09K11/06C09K2211/1007C07C2601/04G01N21/643
Inventor 白蕾霍淑慧徐长明卢小泉
Owner NORTHWEST NORMAL UNIVERSITY
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