Method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose

A technology of nicotinamide ribose and mononucleotide, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of difficult reaction purification, low yield, and difficult amplification.

Inactive Publication Date: 2018-12-21
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] These two routes all have problems such as low yield (less than 28%), difficult reaction purification, poor intermediate stability, and difficult amplification (both need to be separated by activated carbon chromatography)

Method used

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  • Method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose
  • Method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose
  • Method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Example 1: Preparation of β-nicotinamide mononucleotide

[0086] a. Condensation (that is, preparation of nicotinic acid ethyl ester triacetyl riboside):

[0087] In a 1L three-necked flask, add tetraacetyl ribose (20g, 62.8mmol), 20mL of dichloromethane, stir and dissolve, then add ethyl nicotinate (14.3g, 94.3mmol), stir well; at room temperature, add dropwise with 20mL of dichloromethane Diluted trimethylsilyl trifluoromethanesulfonate (TMsOTf 21g, 94.3mmol) was exothermic during the dropwise addition, the temperature was controlled below 40°C, the addition was completed within about 0.5 hours, the dropwise addition was completed, and then the reaction was stirred for 0.5-1 hours to complete the reaction (elimination of tetraacetyl ribose monitored by TLC). After the reaction was completed, the reaction solution was cooled to below -5°C, 10 mL of ethanol was added dropwise, and the reaction was terminated by stirring for 15 min to destroy the TMSOTf quenching reacti...

Embodiment 2

[0095] Example 2: Preparation of β-nicotinamide mononucleotide

[0096] a. Condensation (that is, preparation of nicotinic acid ethyl ester triacetyl riboside):

[0097] Add tetraacetyl ribose (10g, 31.4mmol) and 10mL of dichloromethane to a 1L three-necked flask, stir and dissolve, then add ethyl nicotinate (7.1g, 47.1mmol), stir well; at room temperature, add dropwise 10mL of dichloromethane Diluted trimethylsilyl trifluoromethanesulfonate (TMsOTf 10.5 g, 47.1 mmol) was exothermic during the dropwise addition, and the temperature was controlled below 40°C, the addition was completed within about 0.5 hours, the dropwise addition was completed, and then the reaction was stirred for 0.5~ 1 hour to complete the reaction (elimination of tetraacetyl ribose monitored by TLC). After the reaction was completed, the reaction solution was cooled to below -5°C, 5 mL of ethanol was added dropwise, and the reaction was terminated by stirring for 15 min to destroy the TMSOTf quenching rea...

Embodiment 3

[0105] Example 3: Preparation of β-nicotinamide ribose

[0106] a. Condensation (that is, preparation of nicotinic acid ethyl ester triacetyl riboside):

[0107] In a 1L three-necked flask, add tetraacetyl ribose (20g, 62.8mmol), 20mL of dichloromethane, stir and dissolve, then add ethyl nicotinate (14.3g, 94.3mmol), stir well; at room temperature, add dropwise with 20mL of dichloromethane Diluted trimethylsilyl trifluoromethanesulfonate (TMsOTf 21g, 94.3mmol) was exothermic during the dropwise addition, the temperature was controlled below 40°C, the addition was completed within about 0.5 hours, the dropwise addition was completed, and then the reaction was stirred for 0.5-1 hours to complete the reaction (elimination of tetraacetyl ribose monitored by TLC). After the reaction was completed, the reaction solution was cooled to below -5°C, 10 mL of ethanol was added dropwise, and the reaction was terminated by stirring for 15 min to destroy the excess TMSOTf to quench the rea...

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Abstract

The invention belongs to the field of chemical synthesis, and particularly relates to a method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose, which aims at solving the technical problem of providing a method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose. The method comprises the following steps of performing condensation, deacetylation, phosphorylation and ammonolysis on ethyl niacinate and tetraacetyl ribose, so as to obtain the beta-niacinamide single nucleotide; performing condensation, deacetylation, and ammonolysis on ethyl niacinate and tetraacetyl ribose, so as to obtain the beta-niacinamide ribose. Compared with the conventional methods, the method has the advantages that the operation is simple, the amplification is easy,the purification is easy, the yield rate is high, and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing beta-nicotinamide mononucleotide or beta-nicotinamide ribose. Background technique [0002] β-nicotinamide mononucleotide (NMN) is a synthetic substrate of coenzyme I, and NMN is also used in anti-aging research. In cooperation with Keio University in Japan and the University of Washington in the United States, human clinical trials are being conducted on the anti-aging effect and safety of β-NMN. Studies have shown that β-NMN can also regulate the secretion of insulin and also affect the expression level of mRNA. β-NMN has a wide range of application prospects in the field of medical treatment. [0003] β-Nicotinamide ribose (NR) is a derivative of vitamin B3 (also known as niacin). Numerous studies have shown that nicotinamide ribose can enhance the body's metabolism, and it is initially shown to be important in preventing stem cell aging and maintainin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/048C07H1/00
CPCC07H1/00C07H19/048
Inventor 魏霞蔚魏于全
Owner SICHUAN UNIV
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