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Photochemical demethylation of n6-methyladenine

A methyladenine and demethylation technology, which is applied in the fields of chemical biology and organic chemistry, can solve the problems of excess, low conversion efficiency, and low biological tolerance, and achieve the advantages of precise controllable adjustment and wide selection range

Inactive Publication Date: 2019-01-11
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has played a role in promoting the mechanism of related demethylated proteins, but this method requires the use of excess hydrogen peroxide (50-100 equivalents), low biotolerance and low conversion efficiency (39%), etc. kind of defect

Method used

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  • Photochemical demethylation of n6-methyladenine
  • Photochemical demethylation of n6-methyladenine
  • Photochemical demethylation of n6-methyladenine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] with vitamin B 2 N for photosensitizer under 470nm wavelength blue light and Selectfluor 6 -Methyladenine demethylation: add N to the reaction tube in turn 6 - Methyladenine (0.2mmol, 29.8mg), Selectfluor (0.44mmol, 155.8mg), Vitamin B 2 (0.02mmol, 7.5mg), add 4ml H under the protection of nitrogen 2 O / CH 3 CN(1 / 1) solution, irradiated under blue light with a wavelength of 470nm, stirred for 3 hours, added an appropriate amount of sodium bicarbonate until the pH of the reaction solution was 7, spin-dried the liquid, and column chromatography (n-BuOH / H 2 O / MeOH=4 / 1 / 1) isolated 19 mg of adenine with a yield of 71%. 1 H NMR (DMSO-d 6 , 300MHz) δ12.8(s, 1H), 8.1(d, J=5.4Hz, 2H), 7.1(s, 2H).

Embodiment 2

[0040] with vitamin B 2 N for photosensitizer under 470nm wavelength blue light and Selectfluor 6 - Demethylation of methyladenine deoxyribonucleoside: add N to the reaction tube in turn 6 - Methyladenine deoxyribonucleoside (0.1mmol, 26.5mg), Selectfluor (0.22mmol, 78mg), Vitamin B 2 (0.01mmol, 3.8mg), under nitrogen protection, add 2ml H 2 O / CH 3 CN(1 / 1) solution, irradiated under blue light with a wavelength of 470nm, stirred for 3 hours, added an appropriate amount of sodium bicarbonate until the pH of the reaction solution was 7, spin-dried the liquid, and column chromatography (CH 2 Cl 2 / MeOH=12 / 1) to isolate 15 mg of adenine deoxyribonucleoside with a yield of 60%. 1 H NMR (DMSO-d 6 ,300MHz)δ8.33(s,1H),8.13(s,1H),7.31(s,2H),6.36-6.31(m,1H),5.31(d,J=4.2Hz,1H),5.26-5.22 (m,1H), 4.42-4.38(m,1H),3.89-3.86(m,1H),3.65-3.60(m,1H),3.58-3.48(m,1H).

Embodiment 3

[0042] Use 1,4-dicyanobenzene as photosensitizer to make N 6 - Demethylation of methyl adenine ribonucleoside: add N to the reaction tube in sequence 6 -Methyl adenine ribonucleoside (0.1mmol, 28.1mg), Selectfluor (0.22mmol, 77.9mg), 1,4-dicyanobenzene (0.01mmol, 1.3mg), add 2ml of H under nitrogen protection 2 O / CH 3 CN(1 / 1) solution, irradiated under 303nm wavelength ultraviolet rays, stirred for 8 hours, added an appropriate amount of sodium bicarbonate until the pH of the reaction solution was 7, spin-dried the reaction solution, and column chromatography (CH 2 Cl 2 / MeOH=12 / 1) to isolate 25 mg of adenine ribonucleoside with a yield of 95%. 1 HNMR (DMSO-d 6 ,500MHz)δ8.35(s,1H),8.14(s,1H),7.34(s,2H),5.88(d,J=6.0Hz,1H),5.46-5.41(m,2H),5.20(d ,J=4.5Hz,1H), 4.63-4.60(m,1H),4.16-4.14(m,1H),3.98-3.96(m,1H),3.69-3.65(m,1H),3.58-3.53(m , 1H). 13 C NMR (DMSO-d 6 ,125MHz)δ156.6,152.8,149.5,140.4,119.8,88.4,86.3,73.9, 71.1,62.3.

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Abstract

The invention relates to a specific photochemical demethylation method for N6-methyladenine and application of N6-methyladenine. According to the method, light is used as an initiator; and under the existence of a solvent, N6-methyladenine as shown in the formula I or a derivative of N6-methyladenine reacts with a photosensitizer and an oxidant under an illumination condition, thus obtaining a demethylated product as shown in the formula II and realizing demethylation. By the use of the photochemical demethylation method for the N6-methyladenine and relevant compounds, chemical adjustment of nucleic acid under a non-enzymic condition can be adjusted. The invention provides an effective research method on nucleic acid demethylation for the field of researches on epigenetics and chemicobiology.

Description

technical field [0001] The invention relates to the fields of chemical biology and organic chemistry, in particular to N 6 - Process for photochemical demethylation of methyladenine and its derivatives. Background technique [0002] In the field of epigenetics, the study of methylation and demethylation of nucleic acids is one of the most important contents. The hypermethylation of gene regulatory regions usually leads to the silencing of downstream genes, while the demethylation process is usually accompanied by the activation of expression of downstream genes, thus participating in corresponding biological processes. N 6 -Methyladenine (m 6 A) is one of the most common and abundant chemical modifications in eukaryotes, with about 12,000 N in more than 7,000 human genes 6 -Methyladenine modification site, which plays a fundamental regulatory role in broad-spectrum gene expression. N 6 -Methyladenine is widely distributed in RNA such as tRNA, rRNA and snRNA, accounting...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/34C07H19/167C07H19/16C07H1/00
CPCC07D473/34C07H1/00C07H19/16C07H19/167
Inventor 程靓谢丽君刘利
Owner INST OF CHEM CHINESE ACAD OF SCI
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