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Methods of synthesizing nucleotides or nucleotide analogs

A technology of nucleotides and analogs, applied in the field of biosynthesis, can solve problems such as not suitable for nucleotide synthesis

Active Publication Date: 2021-10-19
SHENZHEN HUADA GENE INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are various commercial sodium phosphate, potassium phosphate, sodium pyrophosphate, and potassium pyrophosphate salts on the market. Although their prices are not high, they are not suitable for direct use in the synthesis of nucleotides.

Method used

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  • Methods of synthesizing nucleotides or nucleotide analogs
  • Methods of synthesizing nucleotides or nucleotide analogs
  • Methods of synthesizing nucleotides or nucleotide analogs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Embodiment 1 does not add phase transfer catalyst

[0072]

[0073] Mix the substrate (1.0eq) and the proton sponge (2.0eq) in a 100mL two-necked bottle, and add magnetons. Dissolve the above mixture in 12 mL of PO(OMe) 3 In the middle, use a high vacuum oil pump to pump up for 5 minutes, and change the argon gas in the tee until no bubbles are generated, and repeat the operation 3 times. After stirring for 10 minutes at -15°C, add POCl to the above mixed solution 3 (2.0eq), then stirred for 2-3 hours under ice bath, and another dry 100mL two-necked flask was added to the magnetic stirrer K 4 PPi(5.0eq), Bu 3 N (5.0eq), inject dry DMF (12mL), and pump it on a high vacuum oil pump for 5 minutes, use a tee to change argon, repeat 3 times. Under ice bath and nitrogen protection, the first step reaction solution was added dropwise to K 4 In the PPi flask, wash the bottle with 10 mL of DMF, and continue to stir for 12 hours under an ice bath. HPLC proved that no pro...

Embodiment 2

[0074] Embodiment 2 adds trimethylamine hydrochloride (tertiary ammonium salt) as phase transfer catalyst

[0075]

[0076] Mix the substrate (1.0eq) and the proton sponge (2.0eq) in a 100mL two-necked bottle, and add magnetons. Dissolve the above mixture in 12 mL of PO(OMe) 3 In the middle, use a high vacuum oil pump to pump up for 5 minutes, and change the argon gas in the tee until no bubbles are generated, and repeat the operation 3 times. After stirring for 10 minutes at -15°C, add POCl to the above mixed solution 3 (2.0eq), then stirred for 2-3 hours under ice bath, and another dry 100mL two-necked flask was added to the magnetic stirrer K 4 PPi (5.0eq), trimethylamine hydrochloride (0.5eq) and Bu 3 N (5.0eq), inject dry DMF (12mL), and pump it on a high vacuum oil pump for 5 minutes, use a tee to change argon, repeat 3 times. Under ice bath and nitrogen protection, the first step reaction solution was added dropwise to K 4 In the PPi flask, wash the bottle with 10...

Embodiment 3

[0077] Embodiment 3 adds tetrabutylammonium bromide (0.2eq) as phase transfer catalyst

[0078]

[0079] Mix the substrate (1.0eq) and the proton sponge (2.0eq) in a 100mL two-necked bottle, and add magnetons. Dissolve the above mixture in 12 mL of PO(OMe) 3 In the middle, use a high vacuum oil pump to pump up for 5 minutes, and change the argon gas in the tee until no bubbles are generated, and repeat the operation 3 times. After stirring for 10 minutes at -15°C, add POCl to the above mixed solution 3 (2.0eq), then stirred for 2-3 hours under ice bath, and another dry 100mL two-necked flask was added to the magnetic stirrer K 4 PPi (5.0eq), tetrabutylammonium bromide (0.2eq) and Bu 3 N (5.0eq), inject dry DMF (12mL), and pump it on a high vacuum oil pump for 5 minutes, use a tee to change argon, repeat 3 times. Under ice bath and nitrogen protection, the first step reaction solution was added dropwise to K 4 In the PPi flask, wash the bottle with 10 mL of DMF, and con...

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Abstract

The invention provides a method for synthesizing nucleotide or nucleotide analogs. According to the method, nucleoside and phosphate, pyrophosphate or tripolyphosphate are subjected to a nucleophilic substitution reaction under catalysis of a phase transfer catalyst so as to obtain the nucleotide or the nucleotide analogs, the phosphate, pyrophosphate or tripolyphosphate is non-ammonium phosphate salt, wherein the nucleoside has a structure as shown in a formula (I) or a stereoisomer, a tautomer, a pharmaceutically acceptable salt or a prodrug of the stereoisomer, the tautomer and the pharmaceutically acceptable salt of the structure as shown in the formula (I),.

Description

technical field [0001] The present invention relates to the field of biosynthesis, in particular, the present invention relates to a method for synthesizing nucleotides or nucleotide analogs. Background technique [0002] Nucleotide compounds play an important role in chemistry, biology and chemical biology. Nucleotides are the basic components of all biological cells, and also play a dominant role in the growth, development, reproduction, and inheritance of organisms. Therefore, nucleotides are widely used in national economic construction. For example, deoxynucleoside triphosphate and deoxynucleoside hexaphosphate are widely used as DNA sequencing reagents in DNA sequencing. Nucleoside monophosphate can be used as an important component in infant milk powder. additive. [0003] The synthesis of various nucleotides and nucleotide analogs has important economic and scientific significance. At present, enzyme-catalyzed synthesis and chemical synthesis are the main methods ...

Claims

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Application Information

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IPC IPC(8): C07H19/10C07H1/04
CPCC07H19/10C07H1/04
Inventor 滕波沈亮张泳辉卓世添章文蔚李汉东
Owner SHENZHEN HUADA GENE INST
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