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Method for synthesizing DNA coded sulfone compound through on-DNA free radical reaction promoted by visible light

A synthesis method and compound technology, applied in the field of synthesis of DNA-encoded sulfone compounds, can solve problems affecting the universality of reaction substrates and DNA screening results, etc.

Pending Publication Date: 2021-08-31
SUN YAT SEN UNIV
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  • Application Information

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Problems solved by technology

The above methods all require the participation of metal photocatalysts and conditions in the aqueous phase to complete. Metal residues may affect the recovery of DNA and the screening results of DNA-encoded compound libraries. The solubility of organic substances in the aqueous phase will affect the universality of reaction substrates. sex

Method used

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  • Method for synthesizing DNA coded sulfone compound through on-DNA free radical reaction promoted by visible light
  • Method for synthesizing DNA coded sulfone compound through on-DNA free radical reaction promoted by visible light
  • Method for synthesizing DNA coded sulfone compound through on-DNA free radical reaction promoted by visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Step 1: Synthesis of DNA-encoded halogenated aromatic compound (I)

[0029]

[0030] DNA-NH 2 (4μmol), DMTMM (1M, 3mL), 3-iodo-1H-indole-6-carboxylic acid (1M, 0.4mL) were added to borax buffer solution (pH=9.5, 100mM, 3mL), and reacted at room temperature for 2h, and the reaction After completion, ethanol (15 mL) and NaCl solution (5M, 0.4 mL) were added to precipitate the DNA. Add water, acetonitrile and DIPEA to the sample tube containing the obtained precipitate, and react at 70°C for 12h. After the reaction was completed, ethanol (15 mL) and NaCl solution (5 M, 0.4 mL) were added to precipitate the DNA-encoded halogenated aromatic compound (I-a). The structure of the compound was determined by LC-MS, and the yield was 81%.

[0031] Step 2: Free radical coupling reaction of DNA-encoded halogenated aromatic compound (I-a) and sodium sulfinate (II-a)

[0032]

[0033] Immobilize the DNA-encoded halogenated aromatic compound (I-a, 10nmol) on the resin, wash with...

Embodiment 2

[0035] Using the same method as in Example 1, the reaction solvent in step 2 was replaced by DMSO with DMA to obtain a DNA-encoded sulfone compound (III-a) with a yield of 79%.

Embodiment 3

[0037] Using the same method as in Example 1, the light source in the step 2 reaction was replaced by a 365 nm light source with a 455 nm light source to obtain a DNA-encoded sulfone compound (III-a) with a yield of 46%.

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Abstract

The invention relates to a method for synthesizing a DNA coded sulfone compound through an on-DNA free radical reaction promoted by visible light. The invention provides a novel method for synthesizing the DNA coded sulfone compound promoted by visible light. According to the method, an electron donor-receptor compound electron conversion and solid-phase synthesis strategy is adopted, and free radical coupling reaction of aryl halide and sodium sulfinate under the condition of an organic solvent is completed under the promotion of light. The method comprises the following steps: immobilizing on-DNA halogenated aromatic hydrocarbon, adding an organic solvent, micromolecular sodium sulfinate and alkali, and reacting for a certain time under the irradiation of a light source with a certain wavelength to obtain the DNA coded sulfone compound. No transition metal photocatalyst participates in the reaction, the conditions are mild, the operation is convenient, the substrate universality is good, the product yield is high, and the method is suitable for constructing a DNA coded compound library.

Description

technical field [0001] The invention belongs to the technical field of DNA-encoded compound libraries, and specifically relates to a strategy for transferring electrons through electron donor-acceptor complexes promoted by visible light, so as to realize the activation of DNA-encoded raw materials and complete the combination of small-molecule sodium sulfinate and DNA-encoded halogenated aromatic hydrocarbons. A new method for the synthesis of a class of DNA-encoded sulfone compounds was developed. Background technique [0002] Combinatorial chemistry can use the "combination-resolution" strategy to quickly construct a compound library with a large number of compounds, but the identification of compound structures restricts the development of this type of method. In 1992, Professors Sydney Brenner and Richard Lerner of the Scripps Research Institute in the United States proposed the concept of a DNA-encoded compound library (Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5381), whi...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H21/02
CPCC07H1/00C07H21/02Y02B20/00
Inventor 张学景林碧真鄢明
Owner SUN YAT SEN UNIV
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