Preparation method of N-acetylneuraminic acid dihydrate

A technology of neuraminic acid dihydrate and acetylneuraminic acid, which is applied in the field of biochemistry, can solve the problems of strong corrosion of reaction equipment, low preparation efficiency, and slow crystallization speed on standing, and achieve high stability, mild conditions, and high efficiency. high effect

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

[0007] However, in the existing N-acetylneuraminic acid hydrate preparation process, the glacial acetic acid crystallization method and the method of adjusting the hydrogen ion concentration of the solution will use a large amount of volatile acidic solution, which is not only harmful to the health of the operator, but also acidic. The solution will cause strong corrosion to the reaction equipment, which greatly increases the equipment depreciation and loss costs in production
Although the supersaturated crystallization method does not use corrosive substances, the standing crystallization speed is slow and the preparation efficiency is low, which is not conducive to large-scale industrial production

Method used

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  • Preparation method of N-acetylneuraminic acid dihydrate
  • Preparation method of N-acetylneuraminic acid dihydrate
  • Preparation method of N-acetylneuraminic acid dihydrate

Examples

Experimental program
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Effect test

Embodiment 1

[0048] This embodiment provides a preparation method of N-acetylneuraminic acid dihydrate, the specific steps are as follows:

[0049] (1) Mix 5g of N-acetylneuraminic acid with 100mL of pure water. After it is completely dissolved, add 0.2g of activated carbon to the aqueous solution of N-acetylneuraminic acid, and decolorize it in a constant temperature oscillating water bath at 30°C for 15 minutes. Then filter with a 0.22 μm filter membrane to collect the filtrate;

[0050] (2) Add 5 times the volume of acetonitrile to the filtrate obtained in step (1), let stand at 4°C for crystallization for 12 hours, then filter with a 0.22 μm filter membrane to collect the solid phase;

[0051] (3) The solid phase obtained in step (3) was washed with 75% aqueous ethanol, and then dried in an oven at 60° C. under normal pressure for 4 hours to obtain the N-acetylneuraminic acid dihydrate crystal.

Embodiment 2

[0053] This embodiment provides a preparation method of N-acetylneuraminic acid dihydrate, the specific steps are as follows:

[0054] (1) Mix 10g of N-acetylneuraminic acid with 100mL of pure water, and after it is completely dissolved, use a 0.22μm filter membrane to remove impurities and collect the filtrate;

[0055] (2) Add 7 times the volume of acetone to the filtrate obtained in step (1), let stand at 25°C for crystallization for 24 hours, then filter with a 0.22 μm filter membrane to collect the solid phase;

[0056] (3) The solid phase obtained in step (3) was washed with 75% ethanol aqueous solution, and then dried in a vacuum oven at 40° C. for 6 hours to obtain the N-acetylneuraminic acid dihydrate crystal.

Embodiment 3

[0058] This embodiment provides a preparation method of N-acetylneuraminic acid dihydrate, the specific steps are as follows:

[0059] (1) Mix 20g of N-acetylneuraminic acid with 100mL of pure water. After it is completely dissolved, add 0.3g of activated carbon to the aqueous solution of N-acetylneuraminic acid, and decolorize it in a constant temperature oscillating water bath at 40°C for 30 minutes. Then filter with a 0.22 μm filter membrane to collect the filtrate;

[0060] (2) Add 10 times the volume of crystallization hydration agent (equal volume mixture of acetonitrile and acetone) to the filtrate obtained in step (1), let stand at 10°C for crystallization for 18 hours, then filter with a 0.22 μm filter membrane to collect the solid phase;

[0061] (3) The solid phase obtained in step (3) was washed with 75% ethanol aqueous solution, and then dried in a vacuum oven at 50° C. for 3 hours to obtain the N-acetylneuraminic acid dihydrate crystal.

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Abstract

The invention provides a preparation method of an N-acetylneuraminic acid dehydrate. The preparation method comprises the steps that a crystal water mixture is added into an N-acetylneuraminic acid water solution, static placing is conducted for crystallization, solid-liquid separation is conducted, and the obtained solid phase is the N-acetylneuraminic acid dehydrate; and the crystal water mixture is acetonitrile and/or acetone. According to the preparation method, through matching of the crystal water mixture and the process, an N-acetylneuraminic acid anhydride is bonded with the crystallization water, the N-acetylneuraminic acid dehydrate with high purity and high stability is obtained, the N-acetylneuraminic acid dehydrate has a stable crystal structure, and can be stored stably at 60DEG C for more than 10 days without water loss. According to the provided preparation method of the N-acetylneuraminic acid dehydrate, the efficiency is high, conditions are mild, a strong acid corrosive reagent does not need to be used, and an efficient and environmentally friendly process is achieved.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and in particular relates to a preparation method of N-acetylneuraminic acid dihydrate. Background technique [0002] N-acetyl neuraminic acid (N-acetyl neuraminic acid) is the most common and the largest proportion of the sialic acid family. It is a general term for an acidic amino sugar containing 9 carbon atoms and a pyranose structure. It is a natural The existing carbohydrates were first isolated and purified and their structures determined in the 1950s. N-acetylneuraminic acid is an important natural nutrient, which is synthesized by the liver in the human body, and its content is relatively high in foods such as bird's nest, deer antler, eggs, and milk powder. N-acetylneuraminic acid has important functions in stabilizing protein conformation, cell adhesion and recognition, immune regulation, and anti-virus, especially in the production and development of the brain and nervous system...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/06C07H7/033A61K8/68A61Q19/00A61K31/7012A23L33/10
CPCC07H1/06C07H7/033A61K8/68A61Q19/00A23L33/10
Inventor 袁丽霞朱薇薇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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