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Dinucleotide and synthesis method thereof

A dimeric nucleotide and synthesis method technology, applied in the field of dimeric nucleotide synthesis, can solve problems such as low yield and limited scale production

Pending Publication Date: 2022-02-08
SHANGHAI ZHAOWEI TECH DEV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method also has limited scale production due to equipment limitations
In addition, recently, synthesizers are often used to automatically connect amino acids (polypeptide synthesizers) or nucleotides (DNA, RNA synthesizers) to synthesize the desired structure according to the design, but the yield is not high

Method used

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  • Dinucleotide and synthesis method thereof
  • Dinucleotide and synthesis method thereof
  • Dinucleotide and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] raw material:

[0083] Compound 1

[0084] Compound 2

[0085] Raw material treatment: 45.23g (0.9eq) of compound 1 and 34.9g of compound 2 were dehydrated and dried with 350ml of dichloromethane DCM with water.

[0086] In the first step, add the above compound 1 and compound 2 into the flask, and add 4.1 g (1.0 eq) of tetrazole therein. Reacted at 26°C for 14h. Purification: extract with sodium bicarbonate and sodium chloride aqueous solution, dry the organic phase, filter and concentrate; then use 17 times the mass of silica gel chromatography for elution, and the eluent is 10 times the column volume of Hep / EA = 1 / 2. After elution, the eluate containing compound 3 (content 88.09%) was collected, and then the eluate was concentrated to dryness to obtain 40.0 g of solid. The purity of compound 3 was 97.30%.

[0087] Structure of compound 3

[0088] In the second step, 34.5g (1.0ep) of compound 3 was mixed with 345ml of dichloromethane DCM and 7.7mL (1.5eq) ...

Embodiment 2

[0099] Raw material treatment: 31.0 g of compound 1 was added, 39.41 g (0.9 eq) of compound 2 were added and dried with DCM.

[0100] In the first step, compounds 1 and 2 were dissolved in 500ml of DCM, 3.85g (1.0eq) of tetrazole was added, and reacted at 25±2°C for 12h. Then the aqueous solution was extracted, the organic phase was dried, filtered and concentrated, 16 times packed silica gel chromatography, 8 times the column volume Hep / EA=1 / 1.5 elution collected the next column liquid, concentrated under reduced pressure to dryness to obtain 57.0 g of compound 3 product, purity: 83.97% ; The conversion rate of compound 2 was 85.29%.

[0101]

[0102] In the second step, 48.45g (1.0eq) of compound 3 was dissolved in 485ml of DCM, and 11.6ml (1.5eq) of tert-butanol peroxide was added. After reacting at 25±2°C for 1h, TLC monitored that there was no raw material. Use 2.5eq thio Sodium sulfate aqueous solution was quenched, washed twice with water, and 60.0 g of compound 4 (pu...

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Abstract

The invention discloses dinucleotide and a synthesis method thereof, and belongs to the field of biological materials. The synthesis method of the dinucleotide comprises the following step: carrying out polycondensation on 2'hydroxyl of nucleoside and 5 'hydroxyl of deoxynucleoside through a 2'-5 'phosphodiester bond to form the dinucleotide. The dinucleotide is beneficial to screening of nucleotide drugs.

Description

technical field [0001] This application relates to the field of biological materials, in particular, to a method for synthesizing dimeric nucleotides. Background technique [0002] Oligonucleotide usually refers to the general term of a kind of short chain nucleotides with less base content. [0003] Oligonucleotides are often used as probes to determine the structure of DNA or RNA, and are often used in processes such as gene chips, electrophoresis, and fluorescence in situ hybridization, because oligonucleotides are easily linked to their complementary pairs. [0004] At present, the widely used method for preparing oligonucleotides is the solid-phase phosphoramidite method. The principle is that the nucleoside 3' is immobilized on a solid-phase carrier (for example, controllable microporous glass beads / CPG), and a protecting group (for example, dimethoxytrityl / DMT ), so that the direction of synthesis is synthesized from the 3' end with the synthetic primer to the 5' en...

Claims

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Application Information

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IPC IPC(8): C07H21/04C07H1/00
CPCC07H21/04C07H1/00Y02P20/55
Inventor 黄成邱洪健毛忠华李新亮
Owner SHANGHAI ZHAOWEI TECH DEV