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Method for constructing beta-fat substituted ketone compound through On-DNA reaction

A technology for substituted ketones and compounds, applied in the field of constructing On-DNAβ-fatty substituted ketone compounds, can solve problems such as no reports

Pending Publication Date: 2022-04-29
HITGEN INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no report on the synthesis of On-DNA β-fatty substituted ketones from On-DNA α,β-unsaturated carbonyl compounds.

Method used

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  • Method for constructing beta-fat substituted ketone compound through On-DNA reaction
  • Method for constructing beta-fat substituted ketone compound through On-DNA reaction
  • Method for constructing beta-fat substituted ketone compound through On-DNA reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1, the synthesis of On-DNA β-fat substituted ketones

[0057] Step 1. Synthesis of On-DNA α, β-unsaturated carbonyl compounds

[0058]

[0059] DNA-NH 2 (A) Dissolved in 250mM boric acid buffer solution with pH=9.4, and prepared as 1mM concentration solution (20μL, 20nmol); 2-methacrylic acid (25 equivalents, 500nmol, 0.2M DMA solution) and DIPEA (25 equivalents , 500nmol, 0.2M DMA solution) and mix well, then add HATU (25 equivalents, 500nmol, 0.2M DMA solution), mix well, activate at 0°C for 5 minutes; add the activation solution to the DNA solution twice, First react at 0°C for 5 minutes, then place at 25°C for 30 minutes.

[0060] After the reaction, carry out ethanol precipitation: add a total volume of 10% 5M sodium chloride solution to the reacted solution, then continue to add 3 times the total volume of absolute ethanol, shake evenly, and place the reaction in dry ice to freeze 0.5 hours, then centrifuged at 12000rpm at low temperature (4°C) fo...

Embodiment 2

[0065] Embodiment 2, the synthesis of On-DNA β-fat substituted ketones

[0066] According to the preparation method of Example 1, keeping other conditions unchanged, 5 kinds of α, β-unsaturated carbonyl compounds (1-5) were mixed with 6 kinds of fatty boric acids / boric acid esters or trifluoroborates (a-f) respectively Reaction, concrete reaction product productive rate sees accompanying drawing.

[0067]In summary, the present invention controls the solvent, temperature, pH and other conditions during the reaction. In the presence of alkali, On-DNA α, β-unsaturated carbonyl compound and fatty boric acid / boric acid ester or trifluoroboric acid Salt reaction can get On-DNA β-fat substituted ketones. The method has a wide range of substrates, can be carried out in the mixed water phase of organic solvent / water phase, is simple to operate, and is environmentally friendly, and is suitable for the synthesis of a DNA-encoded compound library using a multi-well plate.

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Abstract

The invention relates to a method for constructing a beta-fat substituted ketone compound through On-DNA (deoxyribonucleic acid) reaction, which is characterized in that an On-DNA alpha, beta-unsaturated carbonyl compound is used as a raw material and reacts with fat boric acid / boric acid ester or trifluoroborate in the presence of a photosensitizer and alkali to obtain the beta-fat substituted ketone compound. The method disclosed by the invention can be carried out in a mixed water phase of an organic solvent / water phase, the post-treatment is simple, the condition is mild, a high-diversity DNA coding compound library can be obtained in a relatively short time at a high yield, and the method is suitable for synthesizing DNA coding compounds by a porous plate.

Description

technical field [0001] The invention belongs to the technical field of encoded compound libraries, and in particular relates to a method for constructing On-DNAβ-fatty substituted ketone compounds in a DNA encoded compound library. Background technique [0002] In drug development, especially new drug development, high-throughput screening for biological targets is one of the main means to quickly obtain lead compounds. However, the traditional high-throughput screening based on a single molecule requires a long time, huge investment in equipment, limited number of library compounds (millions), and the construction of a compound library requires decades of accumulation, which limits the efficiency and efficiency of lead compound discovery. possibility. The DNA-encoded compound library technology (WO2005058479, WO2018166532, CN103882532) that has emerged in recent years combines combinatorial chemistry and molecular biology techniques to add a DNA tag to each compound at the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C40B50/08C40B30/04C07H21/04
CPCC40B50/08C40B30/04C07H21/04
Inventor 李进蔡坤良高森刘观赛万金桥
Owner HITGEN INC
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