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Alkynyl modified deoxyadenosine phosphoramidite monomer and preparation method thereof

A technology of deoxyadenosine phosphoramidite and deoxyadenosine, which is applied in the field of medicine, can solve the problems of complex synthetic methods, restrictions on practical application, and many steps, and achieve easy-to-obtain raw materials, high yield, simple reaction and post-treatment Effect

Active Publication Date: 2019-07-05
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis method of deoxynucleosides containing unnatural bases is complex, with many steps and high cost, which restricts its practical application in DNA labeling and functionalization

Method used

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  • Alkynyl modified deoxyadenosine phosphoramidite monomer and preparation method thereof
  • Alkynyl modified deoxyadenosine phosphoramidite monomer and preparation method thereof
  • Alkynyl modified deoxyadenosine phosphoramidite monomer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1: Synthesis of the phosphoramidite monomer modified by the alkynyl group at the adenine base position

[0031] 1. Preparation of N1-carboxymethyl-deoxyadenosine (compound 1)

[0032] Pour 5ml of pH=7.0, 0.1mol / L phosphate buffer solution into a 10ml round bottom flask. Add 1500 mg of iodoacetic acid to the round bottom flask, then add 400 mg of deoxyadenosine, and dissolve with slight heat. Use 5mol / L NaOH solution to adjust the pH value to make pH=7.0. At this time, a large amount of white flocculent solids of inorganic salts were precipitated in the reaction solution, and the solids disappeared when the heating was continued to 50°C. The water bath was refluxed for reaction, the temperature was set to 50°C, and the reaction was carried out for 8 hours. After the reaction, the solution changed from orange to colorless and then to pink. Use 5 mol / L HCl to adjust the pH value of the solution to pH=3. The reaction solution was added to a precooled (-5°C) ace...

Embodiment 2

[0041] Synthesis of Example 2 Alkyne Modified DNA

[0042] In the present invention, the alkynyl-modified deoxyadenosine phosphoramidite monomer compound is synthesized by a DNA synthesizer and purified by a high-performance liquid chromatography to obtain an alkynyl-modified oligonucleotide DNA. The product was confirmed by mass spectrometry, as Figure 4 shown.

[0043] The oligonucleotide sequences used in the present invention are as follows:

[0044] DNA: 5'-AAAA * AAAAAAAAAAAAATT-3'

[0045] where A * Indicates the site of alkynyl modification of deoxyadenosine.

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Abstract

The invention belongs to the technical field of medicines, and discloses a synthetic method and an application of an alkynyl modified deoxyadenosine phosphoramidite monomer compound. According to themethod, an N6 position of deoxyadenosine is carboxylated and modified by alkynyl to obtain an intermediate, and protection of a 5'-terminal hydroxyl group and two-step reaction of 2'-phosphoramidite are implemented to obtain the alkynyl modified deoxyadenosine phosphoramidite monomer compound. Solid-phase synthesis of DNA (deoxyribonucleic acid) is implemented, and the DNA is leaded into oligonucleotide in a fixed point manner to obtain artificial genomic loci alkynyl modified oligonucleotide. The alkynyl modified deoxyadenosine phosphoramidite monomer compound is applied to oligonucleotide alkynyl modification, the method is simple, yield is considerable, new ideas and high-value intermediates are provided for follow-up DNA functionalization, and the compound is wide in application prospects.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to an alkyne-modified deoxyadenosine phosphoramidite monomer compound, in particular to a deoxyadenosine phosphoramidite monomer compound modified by an alkynyl group at the base of adenine. A preparation method and application of an adenosine phosphoramidite monomer compound modified by an alkynyl group. Background technique [0002] In recent years, with the development of nucleic acid chemical synthesis technology, a series of chemically modified oligonucleotide derivatives have been reported in academia and industry. The chemical modification of oligonucleotides includes the modification of the sugar ring, the base position, the modification of the phosphodiester backbone, or the replacement of natural nucleosides with chemical structures with specific functions, etc. These modification methods and the reported oligonucleotide derivatives provide an important material basis for ...

Claims

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Application Information

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IPC IPC(8): C07H19/207C07H21/04C07H1/00
CPCC07H19/207C07H21/04C07H1/00Y02P20/55
Inventor 刘明哲王诗宇
Owner SHENYANG PHARMA UNIVERSITY
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