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Preparation method of nicotinamide mononucleotide

A technology of nicotinamide riboside salt and mononucleotide, which is applied in the field of preparation of nicotinamide mononucleotide, and can solve the problem of low selectivity

Pending Publication Date: 2022-04-19
BEIJING HONGHUI MEDITECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The main purpose of the present invention is to provide a method for preparing nicotinamide mononucleotide to solve the problem of low selectivity in the synthesis method of nicotinamide mononucleotide in the prior art

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  • Preparation method of nicotinamide mononucleotide
  • Preparation method of nicotinamide mononucleotide
  • Preparation method of nicotinamide mononucleotide

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[0027] In a typical embodiment of the present application, a method for preparing nicotinamide mononucleotide is provided, the preparation method comprising: step S1, comprising nicotinamide riboside salt, 1,8-bisdimethylamino The raw materials of naphthalene, phosphorus oxychloride and solvent are phosphorylated to obtain a post-reaction system; in step S2, the post-reaction system is hydrolyzed to obtain a reaction solution containing nicotinamide mononucleotide.

[0028] The 2-hydroxyl on the five-membered heterocyclic ring of nicotinamide riboside salt is the primary hydroxyl group, and the 3 and 4-position hydroxyl groups are secondary hydroxyl groups. Since the primary hydroxyl group is more reactive than the secondary hydroxyl group, when the above phosphorylation reaction occurs, 1, 8-bisdimethylaminonaphthalene preferentially forms a complex with the 2-hydroxyl group of nicotinamide riboside salt, and on the one hand, because 1,8-bisdimethylaminonaphthalene is a rigid ...

Embodiment 1

[0051] Weigh 10g nicotinamide ribose chloride (34.4mmol), add it to a 100mL reaction bottle, add 50mL trimethyl phosphate, cool down to -20~-10°C, add 11.06g 1,8-bisdimethylaminonaphthalene (51.6mmol) , and then dropwise added 26.4g of phosphorus oxychloride (172mmol), reacted for 24h, filtered the reaction solution under reduced pressure and concentrated the filtrate under reduced pressure to obtain a concentrated product.

[0052] Add 20mL of purified water to the concentrated product at a temperature of -10~-5°C. After dissolving, slowly add 200mL of acetonitrile dropwise, stir and crystallize for 4 hours, and filter to obtain 8.62g of β-nicotinamide mononucleotide. The proton nuclear magnetic resonance spectrum of β-nicotinamide mononucleotide products is attached figure 1 , and the H-NMR spectrum data are: 1 H-NMR (600MHz,D 2 ( 1H,d,H-1),4.405-4.420(1H,m,H-2),4.388-4.396(1H,t,H-3),4.249(1H,d,H-4),4.045-4.046( 1H,d,H-5), 3.876-3.896(1H,d,H-5). From attached figure 1 I...

Embodiment 2

[0054] The difference between embodiment 2 and embodiment 1 is that

[0055] The molar ratio of 1,8-bisdimethylaminonaphthalene, nicotinamide ribose chloride (34.4mmol) and phosphorus oxychloride was 1:1:5, and finally 8.05g of β-nicotinamide mononucleotide was obtained.

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Abstract

The invention provides a preparation method of nicotinamide mononucleotide. The preparation method comprises the following steps: carrying out phosphorylation reaction on raw materials containing nicotinamide nucleoside salt, 1, 8-bis (dimethylamino) naphthalene, phosphorus oxychloride and a solvent to obtain a reaction solution containing nicotinamide mononucleotide. On one hand, 1, 8-bis (dimethylamino) naphthalene can inhibit phosphorus oxychloride from continuously attacking 2-position or 3-position hydroxyl; on the other hand, one nitrogen atom of the 1, 8-bis (dimethylamino) is beneficial to removal of hydroxyl hydrogen at the position 2, the other nitrogen atom is beneficial to removal of chlorine in phosphoryl chloride, and removal of hydrogen chloride is facilitated under the synergistic effect of the two nitrogen atoms. Meanwhile, as the distance between two nitrogen atoms in the 1, 8-bis (dimethylamino) naphthalene is short, a transition intermediate formed in the process of removing hydrogen chloride from the 1, 8-bis (dimethylamino) naphthalene is more stable, so that the process of removing hydrogen chloride tends to intramolecular reaction, and the selectivity of phosphorylation reaction is further improved.

Description

technical field [0001] The invention relates to the technical field of nicotinamide mononucleotide synthesis, in particular to a preparation method of nicotinamide mononucleotide. Background technique [0002] Nicotinamide mononucleotide (NMN), also known as β-nicotinamide mononucleotide, as NAD + The intermediate in the salvage pathway has the effect of anti-oxidation and reducing oxidative stress. It is used in the treatment of some specific diseases, such as stroke, cardiac ischemia-reperfusion, Alzheimer's disease, Parkinson's disease, acute kidney injury, It also has good performance in retinal degenerative diseases, type 2 diabetes, etc. Especially in anti-aging, NMN can slow down the physiological decline of organisms, enhance energy metabolism, and prolong life. [0003] [0004] In May 2018, Herbalmax, an American dietary supplement company, transformed the scientific research achievement NMN (Nicotinamide mononucleotide nicotinamide mononucleotide), which has ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/048C07H1/00C07H1/02C07H1/06
CPCC07H19/048C07H1/00C07H1/02C07H1/06
Inventor 李亚彬吕久安杜立民童卫民
Owner BEIJING HONGHUI MEDITECH CO LTD
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