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A bodipy-based fluorescent amino acid and its synthesis method and application

A synthetic method and amino acid technology, applied in the field of medical bioengineering, can solve problems affecting the biological activity of polypeptides, time-consuming, and labor-intensive

Active Publication Date: 2017-03-22
JIANGHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The two methods have their own advantages and disadvantages. The former considers the introduction of fluorescent groups after the peptide is synthesized. It can be directly connected to a certain amino acid residue, or it can be connected to the end of the polypeptide through a bridge. The disadvantage is that the fluorescent group The introduction of the group sometimes affects the biological activity of the polypeptide, and often requires optimization to obtain the ideal labeled peptide, which is time-consuming and labor-intensive; the second method can flexibly and accurately label the fluorescent group on the special site of the polypeptide , thus becoming a new development direction in the field of polypeptide fluorescent labeling

Method used

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  • A bodipy-based fluorescent amino acid and its synthesis method and application
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  • A bodipy-based fluorescent amino acid and its synthesis method and application

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Experimental program
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Effect test

Embodiment 1

[0077] a. Preparation of Intermediate I-1:

[0078] Take a dry 500ml two-neck flask, replace the bottle with nitrogen, add pyrrole (104ml, 1.5mol), benzaldehyde (6mL, 60mmol) and catalyst trifluoroacetic acid (0.67mL, 6mmol), stir at room temperature for 1h, and add a concentration of 1M Quenched with NaOH solution (100 mL), extracted with ethyl acetate (200 mL×3), dried over anhydrous magnesium sulfate, filtered, concentrated, and recrystallized from ethanol to obtain 10.5 g of a brown solid with a yield of 80.7%.

[0079] b. Preparation of Intermediate I-2:

[0080] Intermediate I-1 (5g, 22mmol) was dissolved in 200mL of anhydrous tetrahydrofuran, replaced with a nitrogen system, and a tetrahydrofuran solution (60mL) of chlorosuccinimide (6.5g, 48.4mmol) was added at -78°C, Keep stirring at -78°C for 2 hours, then stir at room temperature for 3 hours. After the reaction, add water (300 mL), extract with dichloromethane (200 mL×3), dry over anhydrous magnesium sulfate, filte...

Embodiment 2

[0105] a. Preparation of Intermediate I-1:

[0106] Take a dry 500ml two-neck flask, replace the bottle with nitrogen, add pyrrole (83.2ml, 1.2mol), benzaldehyde (6mL, 60mmol) and trifluoroacetic acid (1.34mL, 12mmol), stir at room temperature for 2h, add 1M NaOH solution (100 mL), extracted with ethyl acetate (200 mL×3 times), dried over anhydrous magnesium sulfate, filtered, concentrated, and recrystallized from ethanol to obtain intermediate I-1 as a brown solid.

[0107] b. Preparation of Intermediate I-2:

[0108] Intermediate I-1 (5g, 22mmol) was dissolved in 200mL of anhydrous tetrahydrofuran, replaced with a nitrogen system, a tetrahydrofuran solution (60mL) of chlorosuccinimide (8.86g, 66mmol) was added at -78°C, and kept Stir at -78°C for 3 h, then at room temperature for 4 h. After the reaction, add water (300 mL), extract with dichloromethane (200 mL x 3 times), dry over anhydrous magnesium sulfate, filter, and concentrate. Dissolve the obtained product in dichlo...

Embodiment 3

[0129]a. Preparation of Intermediate I-1:

[0130] Take a dry 500ml two-neck flask, replace the bottle with nitrogen, add pyrrole (93.6ml, 1.35mol), benzaldehyde (6mL, 60mmol) and trifluoroacetic acid (1.01mL, 9mmol), stir at room temperature for 1.5h, add 1M NaOH The solution (100 mL) was quenched, extracted with ethyl acetate (200 mL×3 times), dried over anhydrous magnesium sulfate, filtered, concentrated, and recrystallized from ethanol to obtain intermediate I-1 as a brown solid.

[0131] b. Preparation of Intermediate I-2:

[0132] Intermediate I-1 (5g, 22mmol) was dissolved in 300mL of anhydrous tetrahydrofuran, replaced with nitrogen system, and a tetrahydrofuran solution (100mL) of chlorosuccinimide (7.39g, 55mmol) was added at -78°C, and kept Stir at -78°C for 2.5 h, then at room temperature for 3.5 h. After the reaction, add water (300 mL), extract with dichloromethane (200 mL x 3 times), dry over anhydrous magnesium sulfate, filter, and concentrate. Dissolve the o...

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Abstract

The invention discloses a BODIPY-based fluorescent amino acid and its synthesis method and application. The general structural formula of the BODIPY-based fluorescent amino acid is shown in the following formula (I). After preparation, it can not only be directly used for peptide synthesis to prepare fluorescently labeled peptides, but also structurally induce the peptides to form a stable secondary structure, so that the obtained fluorescent peptides have certain biological activities and can be directly used as probes. In the study of the interaction with proteins, it has great practical application prospects.

Description

technical field [0001] The invention relates to the field of medical bioengineering, in particular to a BODIPY-based fluorescent amino acid and its synthesis method and application. Background technique [0002] As one of the three major material foundations of the life system, protein is involved in almost every link of life activities and plays a decisive role in the birth, growth and reproduction of life. The occurrence of many diseases is also closely related to the variation of polypeptides and proteins in the body. Therefore, it is of great significance to select proteins, peptides and amino acid residues closely related to major diseases as targets, and develop highly selective and sensitive detection methods to reveal the mysteries of life, early diagnosis of diseases and screening of drugs. [0003] At present, the detection methods for diagnosing peptides and proteins mainly include immunolabeling, isotope labeling and fluorescence detection. Immunolabeling metho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
Inventor 喻艳华董长治付成喻冰洁罗会秀张冬冬陈俊杰舒婷婷
Owner JIANGHAN UNIVERSITY
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