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A method for preparing β-nicotinamide mononucleotide and its sodium salt

A nicotinamide nucleotide and mononucleotide technology is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., which can solve the problems of high cost, high equipment requirements, slow reaction, etc. Improved yield and purity, good reaction selectivity, and easy purification

Active Publication Date: 2021-02-09
武汉一若生物材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The present invention is to provide a brand-new chemical synthesis method, the purpose of which is to solve the problems of high cost, slow reaction, high requirements on equipment, etc., so as to greatly reduce the cost, have high purity, and be suitable for a new chemical synthesis method suitable for industrial production. method

Method used

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  • A method for preparing β-nicotinamide mononucleotide and its sodium salt
  • A method for preparing β-nicotinamide mononucleotide and its sodium salt
  • A method for preparing β-nicotinamide mononucleotide and its sodium salt

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Embodiment 1

[0047] Embodiment 1 A method for preparing β-nicotinamide mononucleotide, comprising the following steps in sequence:

[0048] A, esterification reaction, reaction formula is as follows:

[0049]

[0050] Under an ice-water bath, add 87g of pyridine and 290g of nicotinamide ribose to 500mL of acetonitrile, control the temperature at 0-5°C, then slowly drop 281g of diphenyl chlorophosphate into it, and continue the reaction under stirring for about 12 Hours until the reaction is complete (TLC plate to see the disappearance of raw material spots).

[0051] After the reaction, the acetonitrile was recovered by distillation under reduced pressure at 40-45°C to obtain about 630 g of the crude product of nicotinamide ribose diphenyl phosphate, an intermediate of β-nicotinamide ribose, with a yield of 100%, all of which were directly used in the next step reaction.

[0052] B, hydrolysis reaction, reaction formula is as follows:

[0053]

[0054] At room temperature (20°C, t...

Embodiment 2

[0058] Embodiment 2 A method for preparing β-nicotinamide mononucleotide, comprising the following steps in sequence:

[0059] a. Esterification reaction

[0060] Under an ice-water bath, add 150g of pyridine and 500g of nicotinamide ribose to 1000mL of DMF, control the temperature at 0-5°C, and then slowly drop 485g of diphenyl chlorophosphate into it, and continue the reaction for about 12 hours to complete the reaction ( TLC plate to see disappearance of raw material spots).

[0061] After the reaction, the DMF was recovered by distillation under reduced pressure at 40-50°C, and about 1100 g of crude product of nicotinamide ribose diphenyl phosphate, an intermediate of β-nicotinamide ribose, was obtained, with a yield of 100%, all of which were directly used in the next step reaction.

[0062] b. Hydrolysis reaction

[0063] At room temperature, the crude intermediate nicotinamide ribose diphenyl phosphate obtained in the previous step was dissolved in 5000 mL of methano...

Embodiment 3

[0067] Embodiment 3 A method for preparing sodium β-nicotinamide mononucleotide, comprising the following steps in sequence:

[0068] a. Esterification reaction

[0069] Under an ice-water bath, add 150g of pyridine and 500g of nicotinamide ribose to 1000mL of acetonitrile, control the temperature at 0-5°C, then slowly drop 485g of diphenyl chlorophosphate into it, and continue the reaction for about 12 hours after the addition is complete (TLC Click the board to see the raw material point disappear).

[0070] After the reaction, acetonitrile was recovered by distillation under reduced pressure at 40-50°C to obtain about 1100 g of crude product of nicotinamide ribose diphenyl phosphate, an intermediate of β-nicotinamide ribose, with a yield of 100%, all of which were directly used in the next reaction .

[0071] b. Hydrolysis reaction

[0072] At room temperature, the intermediate nicotinamide ribose diphenyl phosphate crude product obtained in the previous step was dissolv...

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Abstract

The invention relates to the field of chemical synthesis, in particular to a method for preparing beta-nicotinamide mononucleotide and sodium salt thereof. The method includes: subjecting beta-nicotinamide ribose and diphenyl chlorophosphate to esterification reaction, performing hydrolysis phenyl removing reaction to obtain beta-nicotinamide nucleotide, and adding a certain amount of alkali to the beta-nicotinamide nucleotide to perform alkalization to obtain beta-nicotinamide ribonucleotide sodium. The method is simple to operate, easy to achieve large-scale production, low in cost, good infinal product quality and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing β-nicotinamide mononucleotide (NMN) and its sodium salt. Background technique [0002] The theory of cellular aging points out that the aging of the body is mainly due to the decline of cell function, and the decline of cell function is largely caused by the dysfunction of mitochondria. Mitochondria are the energy factories of the body. When mitochondria are damaged, excessive reactive oxygen species (ie oxidative free radicals) are generated. [0003] Reactive oxygen causes oxidative damage to mitochondrial proteins, lipids, and nucleic acids, which further inhibits oxidative phosphorylation and aggravates the generation of active oxygen, making cells unable to produce enough energy and eventually going to apoptosis. This is the reason why people will slowly age. Studies have shown that the level of NAD+ is particularly important throughout the process ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H1/02C07H1/06C07H19/048
CPCC07H1/00C07H1/02C07H1/06C07H19/048
Inventor 杜小兰程进
Owner 武汉一若生物材料有限公司