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Novel compound L-4-terazine-phenylalanine, preparation method and application thereof

A technology of phenylalanine and L-4-, applied in peptide preparation methods, chemical instruments and methods, organic chemistry, etc., can solve problems such as poor stability, and achieve the effects of easy preparation, high yield, and simplified steps

Inactive Publication Date: 2012-08-08
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage is that the stability of 3,6-(2-pyridine)-tetrazine is relatively poor, and obvious degradation will occur after being placed in aqueous solution for several hours

Method used

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  • Novel compound L-4-terazine-phenylalanine, preparation method and application thereof
  • Novel compound L-4-terazine-phenylalanine, preparation method and application thereof
  • Novel compound L-4-terazine-phenylalanine, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Weigh L-4-cyano-phenylalanine (2.5mmol, 0.475g), formamidine acetate (10mmol, 1.040g), sulfur (2.5mmol, 0.080g) and mix well, add anhydrous hydrazine (100mmol, 3.14 mL), after the addition of anhydrous hydrazine, gas was released and the reactant gradually turned into a yellow viscous substance. After stirring and reacting at room temperature for 22 hours, 15 mL of acetic acid was added to fully dissolve the yellow viscous substance, and the yellow solution was obtained by suction filtration. Weigh sodium nitrite (12.5mmol, 0.863g) and dissolve it in 1.5mL of water, and slowly add it into the above yellow solution under the condition of ice-water bath and stir thoroughly, that is, bubbles are formed, the solution turns purple, and react for 30min. Rotary evaporation removed as much acetic acid as possible to obtain a viscous oil, which was filtered with suction to obtain a purple solid, which was washed with dichloromethane and acetonitrile to obtain 0.3981 g of 4-tetraz...

Embodiment 2

[0037] Weigh L-4-cyano-phenylalanine (2.5mmol, 0.475g), formamidine acetate (5mmol, 0.520g), sulfur (2.5mmol, 0.080g) and mix well, add anhydrous hydrazine (25mmol, 0.785 mL), after the addition of anhydrous hydrazine, gas was released and the reactant gradually turned into a yellow viscous substance. After stirring and reacting at room temperature for 24 hours, 15 mL of acetic acid was added to fully dissolve the yellow viscous substance, and the yellow solution was obtained by suction filtration. Weigh sodium nitrite (10mmol, 0.69g) and dissolve it in 1.5mL of water, and slowly add it into the above yellow solution under the condition of ice-water bath and stir thoroughly, that is, bubbles are formed, the solution turns purple, and react for 60min. Rotary evaporation removed as much acetic acid as possible to obtain a viscous oil, which was filtered with suction to obtain a purple solid, washed with dichloromethane and acetonitrile to obtain 0.3652 g of 4-tetrazine-L-phenylal...

Embodiment 3

[0039]Weigh L-4-cyano-phenylalanine (2.5mmol, 0.475g), formamidine acetate (12.5mmol, 1.300g), sulfur (7.5mmol, 0.240g) and mix well, add anhydrous hydrazine (125mmol, 3.925mL), after the addition of anhydrous hydrazine, gas was released and the reactant gradually turned into a yellow viscous substance. After stirring and reacting at room temperature for 16 hours, 15mL of acetic acid was added to fully dissolve the yellow viscous substance, and the yellow solution was obtained by suction filtration. Weigh sodium nitrite (15mmol, 1.035g) and dissolve it in 1.5mL of water, and slowly add it into the above yellow solution under the condition of ice-water bath and stir thoroughly, that is, bubbles are formed, the solution turns purple, and react for 15min. The acetic acid was removed as much as possible by rotary evaporation to obtain a viscous oil, which was filtered by suction to obtain a purple solid, which was washed with dichloromethane and acetonitrile to obtain 0.4265 g of 4...

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Abstract

The invention discloses a novel amino acid derivative L-4-terazine-phenylalanine (3-(4-(1,2,4,5-tetrazin-3-yl) phenyl)-2-aminopropanoic acid). L-4-cyan-phenylalanine is used as an initial reactant and reacts with formamidine acetate and anhydrous hydrazine under catalysis of sulfur; then the reactants are oxidized by sodium nitrite to generate L-4-1,2,4,5-terazine-phenylalanine. The L-4-1, 2, 4, 5-terazine-phenylalanine is integrated into the biologically active peptide and protein molecules as phenylalanine / tyrosine analogue, and can be applied to on biological orthogonal field based on inverse electronic Diels-Alder reaction as a biomarker; meanwhile, the L-4-1,2,4,5-terazine-phenylalaninethe can be introduced into biologically active peptide as phenylalanine / tyrosine analogue through solid phase polypeptide synthesis method and conduct pharmacological evaluation, so as to improve drug property of certain biologically active peptide.

Description

technical field [0001] The present invention relates to a new compound, L-4-tetrazine-phenylalanine and its preparation method and application. Background technique [0002] In recent years, strategies for labeling biomolecules based on bioorthogonal reactions have emerged. This approach involves the integration of a unique chemical functional group (biorthogonal chemical reporter) onto the target molecule through the cell's own metabolism or chemical modification. Bioorthogonal chemical reporters, functional groups that possess unique reactivity to natural biomolecules and do not interact with each other. Chemical reporters are non-natural, unperturbed, and can be combined with exogenous probes in high-speed and specific reactions in living systems. [0003] In 1900, Hantzsch and Lehmann first synthesized 1,2,4,5-tetrazine, but the yield was very low and unstable, but as a diene, it had high reactivity in cycloaddition reactions. [0004] In 1928, German chemist Diels (O...

Claims

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Application Information

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IPC IPC(8): C07D257/08C07B37/02C07D311/82C07K1/13A61K49/00G01N33/533
Inventor 周兰霞董守良倪中秋
Owner LANZHOU UNIVERSITY
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