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N-acetylneuraminic acid calcium salt crystal and preparation method and application thereof

A technology of acetylneuraminic acid and calcium neuraminic acid, which is applied in the field of biochemistry and can solve the problems of limiting the application of Neu5Ac, low solubility, poor stability of aqueous solution, etc.

Active Publication Date: 2019-12-24
HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, during the application of N-acetylneuraminic acid crystals, the researchers found that the aqueous solution of N-acetylneuraminic acid showed strong acidity, and the solubility was generally small, about 100g / L at room temperature, and N - The stability of acetylneuraminic acid crystals and its aqueous solution is not good, and it will gradually turn dark brown during storage, which greatly limits the application of Neu5Ac

Method used

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  • N-acetylneuraminic acid calcium salt crystal and preparation method and application thereof
  • N-acetylneuraminic acid calcium salt crystal and preparation method and application thereof
  • N-acetylneuraminic acid calcium salt crystal and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0066] This example provides a crystal of N-acetylneuraminic acid calcium salt, the preparation method is as follows:

[0067] (1) Mix calcium hydroxide 0.74g (0.01mol), N-acetylneuraminic acid 6.48g (0.021mol) and 500mL water, stir and react at room temperature for 8h to obtain a reaction solution; add 0.2% activated carbon to the reaction solution , decolorize at 60°C for 30min, filter through a 0.22μm membrane filter, collect the filtrate, and concentrate the filtrate into 15mL reaction solution;

[0068] (2) Add 3 times the volume of ethanol to the reaction solution obtained in step (1), let it stand for crystallization at 4°C for 8h, then filter with a 0.22 μm filter membrane to collect the solid phase; Washed twice with an aqueous ethanol solution, and dried under reduced pressure at 60°C for 12 hours to obtain the N-acetylneuraminic acid calcium salt crystal with a yield of 75%.

Embodiment 2

[0070] This example provides a crystal of N-acetylneuraminic acid calcium salt, the preparation method is as follows:

[0071] (1) Mix calcium hydroxide 0.74g (0.01mol), N-acetylneuraminic acid 6.18g (0.02mol) and 500mL water, stir and react at room temperature for 8h to obtain a reaction solution; add 0.2% activated carbon to the reaction solution , decolorize at 60°C for 30min, filter through a 0.22μm membrane filter, collect the filtrate, and concentrate the filtrate into a 60mL reaction solution;

[0072] (2) Add 2 times the volume of ethanol to the reaction solution obtained in step (1), then raise the temperature of the mixed solution to 70°C, and add ethanol dropwise to the mixed solution until the mixed solution becomes turbid under the condition of maintaining the temperature at 70°C; slowly Cool down to 4°C, stand for crystallization at 4°C for 12 hours, then filter through a 0.22 μm filter membrane to collect the solid phase; wash the solid phase twice with absolute...

Embodiment 3

[0074] This example provides a crystal of N-acetylneuraminic acid calcium salt, the preparation method is as follows:

[0075] (1) Add 61.8g (0.2mol) of N-acetylneuraminic acid into 1500mL water, stir and dissolve completely at room temperature to obtain an aqueous solution of N-acetylneuraminic acid; slowly divide 10g of calcium carbonate (0.1mol) within 30min under stirring conditions Add the above-mentioned N-acetylneuraminic acid aqueous solution in batches, and after the addition of calcium carbonate, stir and react at 40°C for 5 hours to obtain a reaction solution; add 0.2% activated carbon to the reaction solution, decolorize at 70°C for 15 minutes, and use 0.22 Filter through a μm filter membrane, collect the filtrate, and concentrate the filtrate into a 40mL reaction solution;

[0076] (2) Add 5 times the volume of ethanol to the reaction solution obtained in step (1), stand for crystallization at 4°C for 8 hours, then filter with a 0.22 μm filter membrane to collect ...

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Abstract

The invention provides an N-acetylneuraminic acid calcium salt crystal and a preparation method and application thereof. The N-acetylneuraminic acid calcium salt crystal has a molecular formula of (C11H18NO9) 2Ca, has distinct diffraction peaks in a powder X-ray diffraction spectrum, has excellent solubility and high-temperature stability, and does not change color under high-temperature treatmentat 184 DEG C. The N-acetylneuraminic acid calcium salt crystal can be obtained by reacting N-acetylneuraminic acid and a calcium source in an aqueous environment, and then crystallizing and separating. The preparation method is simple, has high yield and purity of the product, and is suitable for large-scale production. The N-acetylneuraminic acid calcium salt crystal with high stability and highsolubility provided by the invention has a high absorption rate, can simultaneously meet supplement requirements of a human body on calcium and N-acetylneuraminic acid, and has wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and specifically relates to an N-acetylneuraminic acid calcium salt crystal, a preparation method and application thereof. Background technique [0002] N-acetylneuraminic acid (N-acetylneuraminic acid, Neu5Ac) is the most important one among more than 50 kinds of sialic acids discovered so far, and its content accounts for more than 99% of all sialic acids. The molecule of Neu5Ac contains 9 carbon atoms and has a pyranose structure. It is mainly located at the end of non-reducing oligosaccharides such as glycoproteins or glycolipids in the form of α-glycosides. It is an acidic amino sugar and is easily soluble in Water, which can be stored stably for a long time in aqueous solution. Neu5Ac is the first contact site for cell information transmission. Its molecular structure is diverse and can participate in multiple physiological processes such as cell recognition, signal transduction, tumo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H7/033C07H1/06C07H1/00C07H13/04A61K31/7012A61P3/02A23L33/125
CPCC07H7/033C07H1/06C07H1/00C07H13/04A61K31/7012A61P3/02A23L33/125C07B2200/13A23V2002/00A23V2250/1578A23V2250/60
Inventor 朱薇薇袁丽霞陈祥松吴金勇王煜王刚费贤春李翔宇孙立洁王纪姚建铭
Owner HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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