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Compound and preparation method thereof, and preparation method of nucleoside oligophosphate

A compound and nucleoside base technology, applied in the field of nucleotide synthesis, can solve problems such as complex synthesis steps, long reaction cycle, and unstable synthesis process, and achieve the effects of shortening the reaction cycle, rapid production, and high yield

Pending Publication Date: 2021-11-09
SHANGHAI ZHAOWEI TECH DEV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the embodiments of the present application is also to provide a method for preparing nucleoside oligophosphates, which aims to improve the synthesis methods of nucleoside oligophosphates in the prior art. The synthesis steps are complicated, the synthesis process is unstable, and the reaction cycle is long. The problem

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  • Compound and preparation method thereof, and preparation method of nucleoside oligophosphate
  • Compound and preparation method thereof, and preparation method of nucleoside oligophosphate
  • Compound and preparation method thereof, and preparation method of nucleoside oligophosphate

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preparation example Construction

[0066] The present application provides a preparation method of a compound, comprising placing nucleoside phosphate raw materials, imidazole and an activator in a first solvent to perform a first reaction. Wherein, the structural formula of activator is as follows:

[0067]

[0068] In the structural formula of the activator: Y is selected from chlorine, bromine and PF 6 at least one of; R 5 selected from hydrogen and C 1 -C 4 At least one of the alkyl groups; R 6 selected from hydrogen, chlorine, bromine, C 1 -C 4 Alkyl and C 1 -C 4 At least one of the alkoxy groups; R 7 for C 1 -C 4 of alkyl.

[0069] As an example, in the structural formula of the activator, R 5 , R 6 and R 7 each independently selected from C 1 -C 4 In the case of an alkyl group, the number of carbon atoms in the alkyl group can be 1, 2, 3 or 4; in the structural formula of the activator, R 6 from C 1 -C 4 In the case of an alkoxy group, the number of carbon atoms in the alkoxy group ...

Embodiment 1

[0176] This embodiment provides a compound and its preparation method.

[0177]The preparation method of the compound: Dissolve nucleoside sodium monophosphate (5.0g) in 100mL of water and acetonitrile mixed solution (volume ratio of water and acetonitrile is 0.01), add activator 2-chloro-1,3-dimethyl Imidazole hexafluorophosphate (34.3g) and imidazole (1.7g) were reacted at 2°C for 0.5h. After the completion of the reaction was monitored by HPLC, the acetonitrile was removed by high vacuum concentration and freeze-dried at -80°C to obtain the compound product (3.8 g, 71%). Wherein, the structural formula of sodium nucleoside monophosphate is as follows:

[0178]

[0179] The structural formula of the obtained compound is as follows:

[0180]

[0181] The compound product that above-mentioned reaction is made carries out HPLC (high performance liquid chromatography) characterization, and characterization result is as follows figure 1 shown. From figure 1 It can be s...

Embodiment 2

[0183] This example provides a preparation method of nucleoside triphosphates.

[0184] Compound (3.5g) was dissolved in 25mL of water, sodium pyrophosphate (Na 4 P 2 o 7 , 4.3g), reacted at 2°C for 4h. After HPLC monitors that the reaction is complete, add deionized water (3.0 L) to dilute, and purify with 80 mL of anion exchange resin, and use ammonium acetate / ammonium bicarbonate / triethylamine-carbonic acid buffer and deionized water as the mobile phase. The purified product was desalted with C18 and directly freeze-dried at -80°C to obtain the nucleoside triphosphate product (2 g, 47.6%). Wherein, the structural formula of compound is as follows:

[0185]

[0186] The structural formula of the nucleoside triphosphate product is as follows:

[0187]

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Abstract

The invention relates to the technical field of nucleotide synthesis, in particular to a compound and a preparation method thereof, and a preparation method of nucleoside oligophosphate. The preparation method of the compound comprises the following steps: putting a nucleoside phosphate raw material, imidazole and an activating agent into a first solvent for a first reaction. According to the invention, the water-soluble raw material and the activating agent are subjected to a reaction to prepare the compound, and the compound can be used as a raw material for synthesizing nucleoside oligophosphate, so that rapid and stable synthesis of nucleoside oligophosphate is facilitated. The phosphate raw material and the compound prepared in the invention are subjected to a second reaction in a second solvent, and then desalination is performed to prepare nucleoside oligophosphate; compared with the prior art, triethylamine conversion does not need to be carried out on the nucleoside phosphate raw material, the utilization rate of the nucleoside phosphate raw material is increased, and the reaction period is shortened.

Description

technical field [0001] The present application relates to the technical field of nucleotide synthesis, in particular, to a compound, a preparation method thereof, and a preparation method of oligophosphate nucleosides. Background technique [0002] Nucleoside oligophosphate nucleosides such as nucleoside diphosphate and nucleoside triphosphate are an important class of biomolecules that maintain the operation of life systems. Due to the presence of high-energy phosphate bonds in the chemical structure of oligophosphate nucleosides, oligophosphate nucleosides are extremely unstable and prone to chemical degradation. However, the current synthesis methods of oligophosphate nucleosides generally have disadvantages such as complicated synthesis steps, unstable synthesis process, and long reaction cycle, which make it impossible to industrially mass-produce oligophosphate nucleosides. Contents of the invention [0003] The purpose of the embodiments of the present application ...

Claims

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Application Information

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IPC IPC(8): C07H19/20C07H19/207C07H1/00C07H1/04
CPCC07H19/20C07H19/207C07H1/00C07H1/04
Inventor 耿佩佩李燕康圆圆姚峰杨阳王晨吴洵燊
Owner SHANGHAI ZHAOWEI TECH DEV
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