CN113956304A - Preparation method of N-acetylneuraminic acid - Google Patents
Preparation method of N-acetylneuraminic acid Download PDFInfo
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- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract
The invention provides a preparation method of N-acetylneuraminic acid. The preparation method comprises the following steps: after the sialic acid-containing solution was decolorized by adsorption, N-acetylneuraminic acid was adsorbed by a strong base anion column. The preparation method of the N-acetylneuraminic acid provided by the invention can optimize the purity and yield of the prepared sialic acid product, the yield can reach more than 90%, and the whiteness of the product is also more than 90%. The method provided by the invention has the advantages of simple operation, low cost, clean production and no environmental pollution.
Description
Technical Field
The invention relates to the technical field of separation and purification, and more particularly relates to a preparation method of N-acetylneuraminic acid.
Background
N-acetylneuraminic acid, also known as sialic acid, is a naturally occurring carbohydrate, and sialic acid plays an important role in the normal development of brain function in children, and is widely used in milk powder or nutrition during or after pregnancy. Sialic acid on the market is usually obtained by fermentation, hydrolysis or extraction, and among them, how to obtain sialic acid with high yield and high purity has been a hot spot of research.
Patent CN10567500c discloses a method for extracting polysialic acid from polysialic acid-producing Escherichia coli fermentation broth, wherein the method uses cation column adsorption and chloroform analysis, has high toxicity, and is not suitable for industrial production. Patent CN102532208B discloses a method for continuously separating sialic acid, which adds a large amount of ethanol and ethyl acetate for mixed extraction, and cannot be recycled at a later stage. Patent CN111386350A discloses a method for purifying sialic acid from fermentation broth, which results in crystals of low purity.
The research team of the applicant extracts and purifies the sialic acid by adopting a conversion crystallization and crystal grading washing mode, obtains a satisfactory effect on the aspect of improving the purity of the sialic acid, but the yield and the economic efficiency cannot be well considered, the industrial production cannot be well met, and a method which has higher yield, can still meet the standard on the purity of the crystal and can realize the process simplification and the cost control needs to be developed.
Disclosure of Invention
The invention aims to provide a preparation method of N-acetylneuraminic acid, which comprises the following steps:
after the sialic acid-containing solution was decolorized by adsorption, N-acetylneuraminic acid was adsorbed by a strong base anion column.
In the prior art, the ion exchange technology is a common technology for purifying sialic acid, but no matter the source of sialic acid, the sialic acid is subjected to protein removal and/or degerming before ion exchange, and the purity and yield of the N-acetylneuraminic acid cannot be considered. Through a large amount of research, the research team of the application finds that before the ion exchange adsorption of sialic acid is carried out, the adsorption decoloration treatment of the stock solution containing sialic acid can optimize the purity and yield of the prepared sialic acid product. The sialic acid is adsorbed by using a strong base type anion column, while the ion exchange technology in the prior art is used for removing impurities, so that the beneficial effect of the sialic acid adsorbing agent cannot be obtained. In the present invention, N-acetylneuraminic acid can be prepared (extracted) by the method of the present invention using a sialic acid-containing solution obtained by the prior art, for example, a sialic acid-containing solution obtained by hydrolysis or a sialic acid-containing solution obtained by fermentation. In the specific examples of the present invention, the present invention is described in detail with reference to a sialic acid-containing solution (i.e., SA fermentation broth) obtained by fermentation, and if not specifically indicated, the SA fermentation broths in the examples and comparative examples are the same, and the content of SA in the same is controlled.
In a preferred embodiment of the present invention, the strongly basic anion column of the present invention is a strongly basic anion resin, including but not limited to anion resins containing quaternary ammonium functional groups. In order to further improve the adsorption effect of SA, the water content of the strong alkali type anion column is preferably 50-60%, the granularity is preferably 20-40 meshes, and the adsorption capacity is preferably 3-5 mmol/g. In practice, commercially available anionic resins containing quaternary ammonium functional groups within the above parameters may be preferably selected, and in the examples of the present invention, the present invention is described in detail with respect to commercially available anionic resins containing quaternary ammonium functional groups of type WSD 260. Among them, in the present invention, the filler amount of the strong base type anionic resin is preferably: the packing was carried out so as to adsorb 20gSA per 100 g. Usually, before the filler is decolorized, the SA content in the solution is detected, the total SA of the materials is calculated, and the filler amount of the strong base type anion resin is calculated according to the required filler amount.
In a preferred embodiment of the present invention, the method further comprises desorbing SA (N-acetylneuraminic acid) -adsorbed strong base anion column from the SA-adsorbed strong base anion column, collecting the desorbed solution, desalting, concentrating, and drying. Preferably, the N-acetylneuraminic acid adsorbed on the strong base anion column is resolved by using a sodium chloride aqueous solution, the resolved solution is collected, desalted and concentrated until the content of the N-acetylneuraminic acid is 80-100 g/L, and the pure product of the N-acetylneuraminic acid is obtained after drying. Among them, the desalting can be carried out by a method generally used in the present invention, and the desalting is carried out until the electric conductivity of the solution is preferably 50us or less. In the invention, preferably, the analytic solution is desalted through a nanofiltration membrane (preferably a 500DA nanofiltration membrane), the clear solution outlet is a salt-containing solution, and whether the salt in the SA solution is completely removed can be judged by detecting the conductivity on line, wherein the conductivity of the clear solution at the outlet is required to be less than 50 us/cm. In the invention, the analyzed strong base type anion column can be regenerated by using a strong base solution (such as a 3-5% sodium hydroxide solution), and the column is washed by pure water until the pH value is about 8-10 and is continuously reused.
In the present invention, "drying" may be performed using a drying method commonly used in the art, and a preferred "drying" step includes: and (3) carrying out spray drying on the concentrated solution to obtain a crude crystal with the water content of not higher than 10%, and carrying out secondary drying at 50-65 ℃ until the water content is not higher than 2% to obtain a pure product, namely the target product. Wherein the temperature of the materials is kept at 50-65 ℃ in the spray drying process, and the secondary drying can be vacuum drying or microwave drying.
In a preferred embodiment of the present invention, the preparation method preferably adsorbs N-acetylneuraminic acid after decolorizing the solution containing sialic acid to a solution color value of not more than 15 °, using a strong base type anion column. Among them, the "adsorptive decoloring" may be carried out by a method commonly used in the art as long as the solution thereof has a colorimetric value of not higher than 15 °. Wherein, the step of "adsorption decoloring" can be: and (3) carrying out adsorption decoloration by using an adsorption medium. The adsorption medium can be decolorized macroporous resin, activated carbon or attapulgite. In the present invention, the decolorization is preferably performed using a decolorized macroporous resin, and the parameters of the decolorized macroporous resin are more preferably: the specific surface area is 480-600 square meters per gram, the pore diameter distribution is 8-9 nm, and the pore volume is 1-3 m3The granularity is 20-40 meshes. The preferable filler amount of the decolorized macroporous resin is 2-3 wt% of the material to be adsorbed. The decolorized macroporous resin can be regenerated by using 3-5% sodium hydroxide solution after adsorption and can be continuously reused.
In a preferred embodiment of the invention, the sialic acid containing solution is preferably a fermentation derived sialic acid solution. Preferably, the fermented liquid containing sialic acid is prepared by degerming and deproteinizing. The step of removing bacteria and protein may be a step commonly used in the art, and in the present invention, the step of "removing bacteria" preferably includes: filtering by using a micro-hollow ceramic membrane under the filtering pressure of 0.2-0.4 Mpa, and collecting clear liquid after top washing by using clear water. The pore diameter of the micro-hollow ceramic membrane can be selected as required, and a micro-hollow ceramic membrane of 200nm is used in the present invention.
The protein removal can be performed by using methods such as centrifugation, sedimentation, filtration, silica gel adsorption and the like, and in a specific embodiment of the invention, the protein removal is performed by using a centrifugation method, and the specific steps can be as follows: and heating the clear liquid after removing the thalli to 75 ℃, and centrifuging at the rotating speed of 4000-8000 r to obtain the clear liquid after removing the protein.
The preparation method of N-acetylneuraminic acid, also called the extraction method of N-acetylneuraminic acid, provided by the invention, before ion exchange for sialic acid adsorption, the sialic acid-containing stock solution is subjected to adsorption decoloration treatment, so that the purity and yield of the prepared sialic acid product can be optimized, the yield can reach more than 90%, the whiteness of the product is also more than 90, and meanwhile, a main anion column in the method can be regenerated and recycled, so that the cost is reduced. The method provided by the invention is simple to operate, can detect the content of substances in key steps on line or in real time, can effectively improve the separation efficiency, and simultaneously realizes the maximum efficient utilization of materials, and has the advantages of low cost, clean production and no environmental pollution.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
The embodiment provides a preparation method of N-acetylneuraminic acid, which comprises the following steps:
1. taking SA fermentation liquor, wherein the SA content is 25 g/L.
2. And (3) removing thalli: filtering with 200nm micro-hollow ceramic membrane under 0.3 MPa.
3. Collecting clear liquid: collecting the clear liquid obtained by filtering, wherein the target product is in the clear liquid.
4. Removing protein from clear liquid: the clear solution was heated to 75 ℃ by plate heat exchanger and passed through centrifuge, conditions: rotating speed is 6000r, and continuously feeding and separating to obtain clear liquid after protein removal.
5. Decoloring and removing impurities:and (4) conveying the clear liquid after protein removal to macroporous resin special for decolorization to remove impurities by adsorption, and obtaining colorless clear liquid. Wherein the amount of the decolorized resin filler is 3 wt% of the total treated materials, and the colorimetric value of the decolorized solution is monitored by an online colorimeter and is 15 degrees; wherein the specific surface area of the macroporous resin special for decolorization is 550 square meters per gram, the pore diameter distribution is 8nm, and the pore volume is 2.1m3The granularity is 30 meshes.
6. Anion column adsorption: adsorbing the N-acetylneuraminic acid in the decolored solution by using strong alkali type anion resin. The packing was carried out so as to adsorb 20gSA per 100 g. The strong base type anion resin is acrylic resin quaternary ammonium group (model WSD260, manufacturer: Anhui tree chemical industry sales Co., Ltd.), has water content of 50%, granularity of 20 meshes and adsorption capacity of 3.6 mmol/g.
7. And (3) analysis: the column was analyzed using 0.2mol/l aqueous sodium chloride solution for the strong base anion having N-acetylneuraminic acid adsorbed thereon, and the change in the SA absorbance in the column solution under analysis was detected by an on-line preparative chromatograph to determine whether complete analysis was achieved.
8. Collecting an analytic solution: and after complete analysis, collecting the analysis solution.
9. Desalting with a nanofiltration membrane: desalting the obtained desorption solution by a 500DA nanofiltration membrane, and completing desalting when the conductivity of the outlet clear liquid is below 50 us/cm.
10. Concentration: after the desalting is completed, the stock solution is continuously concentrated to the SA content of about 100 g/L.
11. Pre-drying: and (3) carrying out spray drying on the obtained concentrated solution to obtain crude SA crystals, wherein the material temperature is maintained at about 60 ℃.
12. Secondary drying: further microwave drying is carried out at the drying temperature of 60 ℃ and the microwave power of 400W, and the obtained N-acetylneuraminic acid (SA) crystal has the content of 98.8 percent, the yield of 90 percent and the whiteness of 94 percent.
Example 2
This example provides a method for preparing N-acetylneuraminic acid, which is the same as that of example 1, except that:
5. decoloring and removing impurities: and adding activated carbon into the clear liquid after protein removal for adsorption and decoloration, and stopping decoloring when the colorimetric value of the solution after decoloration is monitored by an online colorimeter to be not higher than 15 ℃ to obtain colorless clear liquid.
The content of N-acetylneuraminic acid (SA) crystals obtained in this example was 98.4%, the yield was 91%, and the whiteness was 92.
Example 3
This example provides a method for preparing N-acetylneuraminic acid, which is the same as that of example 1, except that:
5. decoloring and removing impurities: and (4) conveying the clear liquid after protein removal to macroporous resin special for decolorization to remove impurities by adsorption, and obtaining colorless clear liquid. Wherein the amount of the decolorized resin filler is 3 wt% of the total processed materials, and the colorimetric value of the decolorized solution is monitored by an online colorimeter and is 20 degrees. Wherein the specific surface area of the macroporous resin special for decolorization is 550 square meters per gram, the pore diameter distribution is 8nm, and the pore volume is 2.1m3The granularity is 30 meshes.
The content of N-acetylneuraminic acid (SA) crystals obtained in this example was 98.0%, the yield was 92%, and the whiteness was 90.
Example 4
This example provides a method for preparing N-acetylneuraminic acid, which is the same as that of example 1, except that:
12. secondary drying: further vacuum drying was carried out at a drying temperature of 60 ℃.
The content of N-acetylneuraminic acid (SA) crystals obtained in this example was 98.1%, the yield was 90%, and the whiteness was 92.
Comparative example 1
The comparative example provides a preparation method of N-acetylneuraminic acid, which comprises the following steps:
1. taking SA fermentation liquor, wherein the SA content is 25 g/L.
2. And (3) removing thalli: filtering with 200nm micro-hollow ceramic membrane under 0.3 MPa.
3. Collecting clear liquid: collecting the clear liquid obtained by filtering, wherein the target product is in the clear liquid.
4. Removing protein from clear liquid: the clear solution was heated to 75 ℃ by plate heat exchanger and passed through centrifuge, conditions: rotating speed is 6000r, and continuously feeding and separating to obtain clear liquid after protein removal.
5. Anion column adsorption: adsorbing the N-acetylneuraminic acid in the decolored solution by using strong alkali type anion resin. The packing was carried out so as to adsorb 20gSA per 100 g. The strong base type anion resin is acrylic resin quaternary ammonium group (model WSD260, manufacturer: Anhui tree chemical industry sales Co., Ltd.), has water content of 50%, granularity of 20 meshes and adsorption capacity of 3.6 mmol/g.
6. And (3) analysis: the column was analyzed using 0.2mol/l aqueous sodium chloride solution for the strong base anion having N-acetylneuraminic acid adsorbed thereon, and the change in the SA absorbance in the column solution under analysis was detected by an on-line preparative chromatograph to determine whether complete analysis was achieved.
7. Collecting an analytic solution: and after complete analysis, collecting the analysis solution.
8. Decoloring and removing impurities: and (4) conveying the resolved solution to macroporous resin special for decolorization, adsorbing and removing impurities to obtain colorless clear liquid. Wherein the amount of the decolorized resin filler is 3 wt% of the total treated materials, and the colorimetric value of the decolorized solution is monitored by an online colorimeter and is 15 degrees; wherein the specific surface area of the macroporous resin special for decolorization is 550 square meters per gram, the pore diameter distribution is 8nm, and the pore volume is 2.1m3The granularity is 30 meshes.
9. Desalting with a nanofiltration membrane: desalting the obtained desorption solution by a 500DA nanofiltration membrane, and completing desalting when the conductivity of the outlet clear liquid is below 50 us/cm.
10. Concentration: after the desalting is completed, the stock solution is continuously concentrated to the SA content of about 100 g/L.
11. Pre-drying: and (3) carrying out spray drying on the obtained concentrated solution to obtain crude SA crystals, wherein the material temperature is maintained at about 60 ℃.
12. And (3) vacuum drying: further vacuum drying was carried out at 60 ℃ to obtain a crystal content of 97.3%, a yield of 83% and a whiteness of 95.
Comparative example 2
1. The SA fermentation broth in this comparative example was an SA fermentation broth with an SA content of 25 g/L.
2. And (3) removing thalli: filtering with 200nm micro-hollow ceramic membrane under 0.3 MPa.
3. Collecting clear liquid: collecting the clear liquid obtained by filtering, wherein the target product is in the clear liquid.
4. Removing protein from clear liquid: the clear solution was heated to 75 ℃ by plate heat exchanger and passed through centrifuge, conditions: rotating speed of 6000r, continuously feeding and separating to obtain clear liquid with protein removed
5. And (3) decoloring: adding activated carbon accounting for 4% of the weight of the protein-removed fermentation liquor into the protein-removed fermentation liquor, and carrying out adsorption decoloration for 0.5h at the temperature of 30 ℃ to obtain decolored fermentation liquor;
6. removing inorganic salts: slowly introducing the decolorized fermentation liquor into a D001 type cation exchange resin column, continuously exchanging, and removing inorganic salts which influence the product purity, such as calcium, magnesium and the like in the deproteinized fermentation liquor to obtain desalted fermentation liquor;
7. and (3) crystallization: concentrating the desalted fermentation liquor by reduced pressure evaporation to 200g/L, adding a mixed solvent of 3 times of methanol and acetic acid (the mixing ratio of the methanol and the acetic acid is 1:4) into the concentrated liquor, cooling to 10 ℃, and crystallizing for 20 hours to obtain crystals;
8. washing and drying: washing the crystallized crystals by absolute ethyl alcohol, and then carrying out temperature programming vacuum drying and drying, wherein the vacuum drying method comprises the steps of vacuum drying at 75 ℃ for 3 hours, then heating to 85 ℃ and then vacuum drying for 4 hours.
The obtained crystal content was 98.2%, the yield was 70%, and the whiteness was 91.
Finally, the method of the present invention is only a preferred embodiment and is not intended to limit the scope of the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A preparation method of N-acetylneuraminic acid is characterized by comprising the following steps:
after the sialic acid-containing solution was decolorized by adsorption, N-acetylneuraminic acid was adsorbed by a strong base anion column.
2. The method of claim 1, wherein the strong base anion column is a strong base anion resin, and the strong base anion resin includes but is not limited to anion resins containing quaternary ammonium functional groups.
3. The method according to claim 1 or 2, wherein the strong base anion column has a water content of 50 to 60%, a particle size of 20 to 40 mesh, and an adsorption capacity of 3 to 5 mmol/g.
4. The method according to any one of claims 1 to 3, wherein the solution containing sialic acid is decolorized by adsorption until the solution color value is not higher than 15 °.
5. The method according to any one of claims 1 to 4, wherein the step of "adsorptive decoloring" is: adsorbing and decoloring by using an adsorption medium; the adsorption medium is decolorized macroporous resin, activated carbon or attapulgite, and preferably is the decolorized macroporous resin.
6. The preparation method according to claim 5, wherein the parameters of the decolorized macroporous resin are preferably: the specific surface area is 480-600 square meters per gram, the pore diameter distribution is 8-9 nm, and the pore volume is 1-3 m3The granularity is 20-40 meshes; the filler amount of the decolorized macroporous resin is 2-3 wt% of the material to be adsorbed.
7. The method according to any one of claims 1 to 6, wherein the sialic acid-containing solution is prepared from a sialic acid-containing fermentation broth by degerming and deproteinizing;
the step of "removing the bacterial body" preferably comprises: filtering by using a ceramic membrane under the filtering pressure of 0.2-0.4 Mpa, and collecting clear liquid.
8. The method according to claim 6 or 7, wherein the protein removing step is sedimentation protein removing, filtration protein removing, silica gel adsorption protein removing or centrifugation protein removing.
9. The production method according to any one of claims 1 to 8, characterized by further comprising the steps of: and (3) resolving the N-acetylneuraminic acid adsorbed on the strong base anion column by using an aqueous solution of sodium chloride, collecting a resolving solution, desalting, concentrating until the content of the N-acetylneuraminic acid is 80-100 g/L, and drying to obtain the N-acetylneuraminic acid.
10. The method for preparing the compound of claim 9, wherein the specific step of drying comprises the following steps: and (3) carrying out spray drying on the concentrated solution to obtain a crude crystal with the water content of not higher than 10%, and carrying out secondary drying at 50-65 ℃ until the water content is not higher than 2%.
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| CN102532208A (en) * | 2012-01-06 | 2012-07-04 | 南京工业大学 | Method for continuously separating sialic acid |
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| CN111386350A (en) * | 2017-11-21 | 2020-07-07 | 詹尼温生物技术有限责任公司 | Method for purifying sialic acid from fermentation broth |
| CN111606958A (en) * | 2020-07-01 | 2020-09-01 | 中科鸿基生物科技有限公司 | Preparation process of high-purity N-acetylneuraminic acid solid |
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2021
- 2021-09-27 CN CN202111138235.3A patent/CN113956304B/en active Active
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| CN102532208A (en) * | 2012-01-06 | 2012-07-04 | 南京工业大学 | Method for continuously separating sialic acid |
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