Method for preparing beta-niacinamide mononucleotide and application thereof

A technology for nicotinamide riboside hydrochloride and mononucleotide, which is applied in the field of preparing beta-nicotinamide mononucleotide and achieves the effects of simple operation and easy amplification

Pending Publication Date: 2019-11-22
SHANGHAI LONGXIANG BIO MEDICINE DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In order to overcome the defects of the existing methods for preparing β-nicotinamide mononucleotide, the present invention provides a method for preparing β-nicotinamide mononucleotide that is easy to operate, high in product purity, high in yield, and capable of tonnage-level industrial production. sour new way

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  • Method for preparing beta-niacinamide mononucleotide and application thereof
  • Method for preparing beta-niacinamide mononucleotide and application thereof
  • Method for preparing beta-niacinamide mononucleotide and application thereof

Examples

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Embodiment 1

[0071] This embodiment discloses a method for preparing β-nicotinic acid amine mononucleotide, comprising the following steps:

[0072] a. Condensation (i.e. preparation of nicotinic acid ethyl triacetyl nucleoside):

[0073] Add tetraacetyl ribose (50g, 0.157mol) and 100mL dichloromethane into a 500ml three-necked flask, stir to dissolve, then add ethyl nicotinate (28.5g, 0.188mol), and stir evenly; at room temperature, add 50mL dichloromethane dropwise Diluted trimethylsilyl trifluoromethanesulfonate (TMsOTf 41.8g, 0.188mol), exothermic during the dropwise addition, the temperature is controlled below 20°C, and the addition is completed within about 0.5 hours. After the dropwise addition is completed, the reaction is stirred for 1 hour To complete the reaction (disappearance of tetraacetylribose monitored by TLC). After the reaction was completed, the reaction liquid was cooled to below -5°C, 15 mL of ethanol was added dropwise, and stirred for 15 min after the addition was...

Embodiment 2

[0081] This embodiment discloses a method for preparing β-nicotinic acid amine mononucleotide, comprising the following steps:

[0082] a. Condensation (i.e. preparation of nicotinic acid ethyl triacetyl nucleoside):

[0083] Add tetraacetylribose (50g, 0.157mol) and 100mL dichloromethane into a 500ml three-necked flask, stir to dissolve, then add ethyl nicotinate (35.5g, 0.235mol), stir evenly; at room temperature, add 50mL dichloromethane dropwise Dilute trimethylsilyl trifluoromethanesulfonate (TMsOTf52.2g, 0.235mol), exothermic during the dropwise addition, control the temperature below 20°C, add within about 0.5 hours, dropwise is complete, then stir for 1 hour To complete the reaction (disappearance of tetraacetylribose monitored by TLC). After the reaction was completed, the reaction liquid was cooled to below -5°C, 25 mL of ethanol was added dropwise, and stirred for 15 minutes after the addition was completed to destroy the TMSOTf quenching reaction, thereby terminat...

Embodiment 3

[0089] This embodiment discloses a method for preparing β-nicotinic acid amine mononucleotide, comprising the following steps:

[0090] a. Condensation (i.e. preparation of nicotinic acid ethyl triacetyl nucleoside):

[0091] Add tetraacetyl ribose (50g, 0.157mol) and 100mL dichloromethane into a 500ml three-necked flask, stir to dissolve, then add ethyl nicotinate (47.4g, 0.314mol), and stir evenly; at room temperature, add 50mL dichloromethane dropwise Diluted trimethylchlorosilane (TMsCl 33.9g, 0.314mol), exothermic during the dropwise addition, controlled temperature below 20°C, added within about 0.5 hour, added dropwise, then stirred for 1 hour to complete the reaction (TLC monitor the disappearance of tetraacetylribose). After the reaction was completed, the reaction liquid was cooled to below -5°C, 30 mL of ethanol was added dropwise, and stirred for 15 minutes after the addition was completed to destroy the quenching reaction of TMSOTf, thereby terminating the reacti...

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Abstract

The invention belongs to the field of chemical synthesis, and in particular, relates to a method for preparing beta-niacinamide mononucleotide and an application thereof. The preparation method comprises the steps: S1, condensation reaction: carrying out condensation reaction of ethyl nicotinate, tetraacetylribose and a catalyst in a first solvent to obtain a solution containing ethyl nicotinate triacetylnucleoside; S2, ammonolysis reaction: carrying out ammonolysis reaction of the solution containing ethyl nicotinate triacetylnucleoside through an ammonia gas solution to obtain niacinamide riboside hydrochloride; and S3, phosphorylation reaction: carrying out reaction of niacinamide riboside hydrochloride with phosphorus oxychloride in a second solvent to obtain beta-niacinamide mononucleotide. Compared with a conventional method, the preparation method has the advantages of simple operation, easy amplification, easy purification, high yield and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing β-nicotinamide mononucleotide and its application. Background technique [0002] coenzyme NAD + , NADH and NADP + , The cellular redox reaction of NADPH is well known, and it is known that NAD + Plays an important role in apoptosis, calcium mobilization, aging, gene expression, immune system regulation, energy metabolism, and metabolic regulation; NAD + Can be synthesized enzymatically and chemically, from vitamin B 3 Various precursors of (nicotinic acid (NA), nicotinamide (Nam), nicotinamide riboside (NR), nicotinamide mononucleotide (NMN)) and tryptophan. NAD + The reaction releases nicotinamide and recycles nicotinamide to form NMN from nicotinamide and 5-phosphoribosylpyrophosphate using nicotinamide phosphoribosyltransferase. Synthetic NMN reacts with ATP and is converted to NAD by nicotinamide mononucleotide adenylyltransferase (NM...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/048C07H1/00A61P35/00A61P9/00A61P25/00A61K31/706
CPCC07H19/048C07H1/00A61P35/00A61P9/00A61P25/00
Inventor 熊毅杨洪
Owner SHANGHAI LONGXIANG BIO MEDICINE DEV CO LTD
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