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Method for synthesizing tetrasodium 5-hydroxymethyl and 5-aldehyde-2'-deoxycytidine triphosphate

A technology of hydroxymethyl deoxycytidine triphosphate tetrasodium salt and aldehyde deoxycytidine triphosphate tetrasodium salt, applied in 5-hydroxymethyl and 5-formyl-2'-deoxycytidine triphosphate tetrasodium salt In the field of salt synthesis, it can solve the problems of unavailable 5-methyl-2'-deoxycytidine triphosphate raw materials and difficult control conditions, and achieve high practical application value, easy method, simple and easy-to-obtain raw materials and reagents

Inactive Publication Date: 2015-05-06
JIANGXI SCI & TECH NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in this method, the raw material of 5-methyl-2'-deoxycytidine triphosphate is not easy to obtain, and the photoreaction requires special equipment, and the conditions are not easy to control

Method used

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  • Method for synthesizing tetrasodium 5-hydroxymethyl and 5-aldehyde-2'-deoxycytidine triphosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] Example 1: 5-Hydroxymethyl-2′-deoxycytidine 5′-triphosphate tetrasodium salt ( 1 )Synthesis

[0009] 1) 5-Hydroxymethyl-2′-deoxycytidine 5′-triethylamine monophosphate ( 4 ) synthesis: under argon protection, the 3 (515 mg, 1.25 mmol) was dissolved in dry trimethyl phosphate (10 mL), and phosphorus trichloride (380 mg, 2.5 mmol) was added to react at 0 °C for 3 hours. Slowly added 0.1 M triethylamine carbonate buffer solution (40 mL) to quench the reaction, then extracted three times with diethyl ether (40 mL), and concentrated the aqueous phase under reduced pressure. Add trifluoroacetic acid (5 mL) and water (5 mL) to the residual oil, react at 20 °C for 1 hour, and concentrate the reaction solution under reduced pressure. Afterwards, methanol (10 mL), potassium carbonate (345 mg, 2.5 mmol) and water (1 mL) were added to the concentrate, reacted at 20 °C for 1 hour, and the reaction solution was concentrated under reduced pressure to obtain a crude product. Usin...

Embodiment 2

[0012] Example 2: 5-Formyl-2′-deoxycytidine 5′-triphosphate tetrasodium salt ( 2 )Synthesis

[0013] 1) 5-formyl-2′-deoxycytidine 5′-phosphoryl piperidine triethylamine salt ( 6 ) synthesis: the 5 (101 mg, 0.2 mmol) was dissolved in methanol (5 mL), activated manganese dioxide (174 mg, 2 mmol) was added, heated to 50 °C for 24 hours, the manganese dioxide was removed by filtration, and the filtrate was concentrated under reduced pressure. Column chromatography separation (dichloromethane: methanol = 5: 1, containing 0.5% triethylamine) to obtain a white solid ( 6 ) 85 mg, yield 84%.

[0014] 2) 5-formyl-2′-deoxycytidine 5′-triphosphate tetrasodium salt ( 2 ) synthesis: under argon protection, the 6 (50 mg, 0.1 mmol) dissolved in dry N , N -Dimethylformamide (2 mL), add tri(tetrabutyl)ammonium pyrophosphate (180 mg, 0.2 mmol) and 4,5-dicyanoimidazole (71 mg, 0.6 mmol) at 20 °C . After reacting for 6 hours, the solvent was removed under reduced pressure, 3 M sodium ac...

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Abstract

The invention relates to a method for synthesizing tetrasodium 5-hydroxymethyl and 5-aldehyde-2'-deoxycytidine triphosphate. The method comprises the following steps of reacting 3'-tert-butyl-dimethylsilyl-5-acetoxymethyl-2'-deoxycytidine (3) and phosphorus oxychloride, removing TBS protecting groups with trifluoroacetic acid / water and removing acetyl groups with potassium carbonate / methanol / water to obtain triethylamine 5-hydroxymethyl-2'-deoxycytidine monophosphate (4); condensing the triethylamine 5-hydroxymethyl-2'-deoxycytidine monophosphate (4) and piperidine in the presence of 2,2'-dimercapto-diphenylamine / triphenylphosphine to obtain 5-hydroxymethyl-2'-deoxycytidine phosphoryl piperidine triethylamine salt (5); activating the 5-hydroxymethyl-2'-deoxycytidine phosphoryl piperidine triethylamine salt (5) and tris(tetrabutyl)ammonium pyrophosphate in the presence of 4,5-dicyanoimidazole to obtain tetrasodium 5-hydroxymethyl deoxycytidine triphosphate; and oxidizing the 5-hydroxymethyl-2'-deoxycytidine phosphoryl piperidine triethylamine salt (5) with activated manganese dioxide to obtain 5-aldehyde-2'-deoxycytidine phosphoryl piperidine triethylamine salt (6) and activating 5-aldehyde-2'-deoxycytidine phosphoryl piperidine triethylamine salt (6) and tris(tetrabutyl)ammonium pyrophosphate in the presence of 4,5-dicyanoimidazole to obtain tetrasodium 5-aldehyde-2'-deoxycytidine triphosphate.

Description

technical field [0001] The invention relates to a new and efficient synthesis method of 5-hydroxymethyl and 5-formyl-2'-deoxycytidine triphosphate tetrasodium salt. technical background [0002] In eukaryotic genomes, 2′-deoxycytidine can be methylated by methyltransferases. This methylation process is one of the most important epigenetic marks in transcriptional gene silencing. Under certain circumstances, DNA methylation facilitates deoxycytidine base repair and also enhances the dynamic flexibility of gene expression during cell development. Studies have shown that 5-methyl-2'-deoxycytidine can generate 5-hydroxymethyl, 5-aldehyde and 5-carboxy-2'-deoxycytidine series oxidation derivatives under the action of TET oxidase. These three nucleoside oxides are thought to be involved in the demethylation process in the regulation of cellular epigenetic programs. In recent years, oligonucleotides have been widely used to study the regulation of this epigenetic program. Howev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/10C07H1/00
CPCY02P20/55C07H19/073C07H1/00
Inventor 孙麒孙剑龚珊珊马茶
Owner JIANGXI SCI & TECH NORMAL UNIV
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