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Method for synthesizing dinucleoside diphosphate and dinucleoside triphosphote

A technology of dinucleoside diphosphate and nucleoside phosphoryl, which is applied in the field of chemical preparation of natural product biochemical reagents, can solve the problems of low reaction yield, difficult separation of by-products, and the need for protection of nucleosides, and achieve easy-to-obtain raw materials , easy product, fast coupling reaction

Inactive Publication Date: 2014-07-09
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the practical application of the above methods, there are still problems such as nucleosides need to be protected, the reaction yield is not high, the reaction speed is slow, and the by-products are difficult to separate.

Method used

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  • Method for synthesizing dinucleoside diphosphate and dinucleoside triphosphote
  • Method for synthesizing dinucleoside diphosphate and dinucleoside triphosphote

Examples

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Embodiment 1

[0013] P 1 , P 2 - Diadenosine-5′,5′-diphosphate disodium salt ( 11 ) Synthesis: adenosine phosphoryl piperidine triethylamine salt ( 3 ,102 mg, 0.2 mmol), adenosine monophosphate triethylamine salt ( 7 , 143 mg, 0.32 mmol) and 4,5-dicyanoimidazole (85 mg, 0.72 mmol) were vacuum-dried in a 25 mL round bottom flask for 2 hours. Under argon protection, 3.0 mL of dry DMF was added and reacted at 20 °C for 16 hours. The reaction solution was concentrated under reduced pressure, and the crude product was obtained after adding sodium acetate aqueous solution (3.0 M, 1.0 mL) and 30 mL ethanol solution for precipitation and centrifugation. After dissolving in deionized water, Sephadex (DEAE-A25) ion-exchange column chromatography to obtain the product triethylamine salt, and then obtained after passing through sodium-type 732 cation-exchange resin P 1 , P 2 - Diadenosine-5′,5′-diphosphate disodium salt 118 mg white solid, yield 82%.

Embodiment 2

[0015] P 1 -Uridine-5′- P 2 - Cytidine-5′-diphosphate disodium salt ( 13 ) Synthesis: Cytidine phosphoryl piperidine triethylamine salt ( 2 , 98 mg, 0.2 mmol), uridine monophosphate triethylamine salt ( 5 , 144 mg, 0.34 mmol) and 4,5-dicyanoimidazole (87 mg, 0.74 mmol) were vacuum-dried in a 25 mL round bottom flask for 2 hours. Under the protection of argon, 3.0 mL of dry DMF was added and reacted at 20 °C for 16 hours. The reaction solution was concentrated under reduced pressure, and the crude product was obtained after adding sodium acetate aqueous solution (3.0 M, 1.0 mL) and 30 mL ethanol solution for precipitation and centrifugation. After dissolving in deionized water, Sephadex (DEAE-A25) ion-exchange column chromatography to obtain the product triethylamine salt, and then obtained after passing through sodium-type 732 cation-exchange resin P 1 -Uridine-5′- P 2 - Cytidine-5′-diphosphate disodium salt 100 mg, yield 74% as white solid.

Embodiment 3

[0017] P 1 -Adenosine-5′- P 2 - Guanosine-5′-diphosphate disodium salt ( 18 ) Synthesis: the guanosine phosphoryl piperidine triethylamine salt ( 4 , 106 mg, 0.2 mmol), adenosine monophosphate triethylamine salt ( 7 , 161 mg, 0.36 mmol) and 4,5-dicyanoimidazole (90 mg, 0.76 mmol) were vacuum-dried in a 25 mL round bottom flask for 2 hours. Under argon protection, 3.0 mL of dry NMP was added and reacted at 40 °C for 6 hours. Add 30 mL of ether solution to precipitate and centrifuge to obtain the crude product. After dissolving in deionized water, Sephadex (DEAE-A25) ion-exchange column chromatography to obtain the product triethylamine salt, and then obtained after passing through sodium-type 732 cation-exchange resin P 1 -Adenosine-5′- P 2 - Guanosine-5′-diphosphate disodium salt 103 mg, yield 70% as white solid.

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Abstract

The invention belongs to the field of chemical synthesis and in particular relates to a method for synthesizing dinucleoside diphosphate and dinucleoside triphosphote. The method comprises the following steps: reacting nucleoside phosphoryl piperidine as a nucleoside phosphoryl donor, nucleoside phosphate or nucleoside diphosphate as a nucleoside phosphoryl receptor and 4,5-dicyanoimidazole (DCI) as an activating reagent in a high-polarity non-protonized solvent; purifying crude products through ion exchange chromatography to obtain dinucleoside diphosphate and dinucleoside triphosphote respectively. According to the method, the selected and used nucleoside phosphoryl piperidine raw material is simple and easily available, the coupling reaction speed is high in the presence of the activating reagent, the yield is high, few byproducts are generated, and the products are easily separated.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to the chemical preparation technology of natural product biochemical reagents, in particular to a series of novel chemical synthesis methods of symmetric and asymmetric dinucleoside diphosphates and dinucleoside triphosphates. technical background [0002] Dinucleoside polyphosphates (Np n N'S) are a large class of special biomolecules. In its molecular structure, two nucleosides are linked by polyphosphoric acid (2-7 phosphate groups). Dinucleoside diphosphate and dinucleoside triphosphate are ubiquitous in mammals and participate in many important life activities inside and outside cells. Compared with mononucleoside polyphosphate, this type of compound has better chemical and metabolic stability, and has important application value in biological research and drug development. For example, nicotinamide adenine dinucleotide (NAD) is a coenzyme that transfers protons, and flavin ...

Claims

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Application Information

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IPC IPC(8): C07H19/10C07H19/20C07H1/04
Inventor 孙麒龚珊珊孙剑刘思
Owner JIANGXI SCI & TECH NORMAL UNIV
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