CN112921061A - Method for producing 2-O-alpha-D-glucopyranosyl-L-ascorbic acid - Google Patents
Method for producing 2-O-alpha-D-glucopyranosyl-L-ascorbic acid Download PDFInfo
- Publication number
- CN112921061A CN112921061A CN202110098548.4A CN202110098548A CN112921061A CN 112921061 A CN112921061 A CN 112921061A CN 202110098548 A CN202110098548 A CN 202110098548A CN 112921061 A CN112921061 A CN 112921061A
- Authority
- CN
- China
- Prior art keywords
- temperature
- ascorbic acid
- glucopyranosyl
- stirring
- alpha
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention relates to a production method of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid, belonging to the technical field of preparation of L-ascorbic acid derivatives. The invention comprises the following steps: (1) dissolving VC in water, adding glucose group donor, stirring at a certain temperature, adjusting pH, adding glycosyltransferase, and stirring; raising the temperature of the reaction solution to 45-50 ℃, keeping the temperature for reacting for 40-50 minutes, stopping heating, reducing the temperature, starting heating when the temperature of the reaction solution is reduced to 25-30 ℃, raising the temperature of the reaction solution to 45-50 ℃, stopping heating, reducing the temperature, repeating the steps, and reacting for 20-30 hours; (2) cooling the temperature of the synthetic liquid to 25-35 ℃, adding alpha-amylase, and stirring; then adding active carbon, stirring and filtering; purifying the filtrate by a column; (3) and (5) freeze drying. The invention simplifies the production process and improves the purity and the conversion rate of the target product.
Description
Technical Field
The invention relates to a production method of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid, belonging to the technical field of preparation of L-ascorbic acid derivatives.
Background
2-O-alpha-D-glucopyranosyl-L-ascorbic acid is also known as vitamin C glucoside (abbreviation AA-2G). The hydroxyl group at the 2-position C of L-ascorbic acid (VC) is substituted by glucopyranoside, and AA-2G is very stable and has significant non-reducing activity compared with VC because of the masking of the glucose group at the 2-position C. After the AA-2G is counted into cells, the cells can be hydrolyzed into VC and glucose, and the antioxidant and whitening effects are the same as those of original VC. Therefore, AA-2G is one of 6 whitening additives approved by the health administration, and is widely applied to various high-end whitening cosmetics. At present, AA-2G internationally applied to whitening cosmetics is monopolized by Nippon Linyuan International Limited, and the selling price thereof is as high as 3000 yuan/kg.
The biotransformation and synthesis by utilizing the specificity of the transglycosylation of the glycosyltransferase is the only production way of AA-2G at present, and mainly comprises three processes of preparation, purification and crystallization. At present, the known AA-2G synthesis method takes starch and L-ascorbic acid as raw materials, the raw materials are catalyzed by glycosyl transferase, the reaction temperature is 60-65 ℃, the reaction time is 30-48h, the conversion rate of AA-2G is 35-40%, and the conversion rate is low.
Patent CN109295134A discloses a method for producing L-ascorbic acid glucoside with high content and high yield, which is based on the idea of using cyclodextrin glucoside transferase to prepare AA-2G, but the AA-2G prepared by the method contains isomers of 5-O- α -D-glucopyranosyl-L-ascorbic acid (abbreviated as AA-5G) and 6-O- α -D-glucopyranosyl-L-ascorbic acid (abbreviated as AA-6G) with direct reduction property, and the later stage requires separation and purification to obtain a product with high purity, and the process is complex.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a production method of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid, which simplifies the production process and improves the purity and the conversion rate of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid.
The production method of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid comprises the following steps:
(1) and (3) synthesis reaction: dissolving VC in 35-45 deg.C water, adding glucose group donor, stirring at a constant temperature for 30-40min, adjusting pH to 5.0-5.5, adding glycosyltransferase, and stirring to obtain reaction solution;
raising the temperature of the reaction solution to 45-50 ℃, keeping the temperature for reacting for 40-50 minutes, stopping heating, reducing the temperature, starting heating when the temperature of the reaction solution is reduced to 25-30 ℃, raising the temperature of the reaction solution to 45-50 ℃, stopping heating, reducing the temperature, repeating the steps, and reacting for 20-30 hours to obtain a synthetic solution;
(2) and (3) purification: cooling the synthetic solution to 25-35 deg.C, adding alpha-amylase, and stirring for 40-50 min; then adding active carbon, stirring for 30-40min, and filtering;
purifying the filtrate by a strong acid cation exchange resin column; the flow rate during purification is 1.5-3 cm/s.
(3) And (3) freeze drying: and (3) performing ultrafiltration and nanofiltration on the filtrate obtained in the step (2), then concentrating until the mass content of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid is 50%, freeze-drying, crushing, sieving and subpackaging to obtain the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid.
Preferably, the glycosyltransferase is an alpha-isomaltosylglucosaccharide forming enzyme and/or a cyclomaltodextrin glucanotransferase.
Preferably, the strongly acidic cation exchange resin is a sulfonic acid group cation exchange resin having a styrene-divinylbenzene copolymer as a matrix.
Preferably, the mass ratio of VC, water, glucose donor and glycosyl transferase is 1-1.2: 80-100: 0.8-1.1: 0.5-0.8.
The invention takes VC and water as substrates, adds a glucosyl donor, adjusts the pH, adds glycosyltransferase which is alpha-isomaltose glucosyl saccharide forming enzyme and/or cyclomaltodextrin glucanotransferase to obtain reaction solution, and after reaction synthesis, the reaction solution is ultrafiltered and nanofiltered, then concentrated, freeze-dried, crushed, sieved and split-packaged to obtain the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid. In the study on the development of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid production by biotransformation, the yellow-sensitive teacher dissolves VC in an acetic acid buffer solution, mixes with a suitable saccharide, adds thiourea, adjusts the pH value and the reaction temperature, and then carries out the reaction. The alpha-isomaltose glucosyl saccharide forming enzyme and/or the cyclodextrin glucanotransferase enzyme can effectively catalyze the disconnection of C bonds in reactants under the conditions of proper temperature and pH, thereby improving the conversion rate and the content.
Compared with patent CN109295134A, the invention is simpler and more convenient in preparation, purification and separation processes. In addition, the glycosyltransferases used in the invention are different, and the production cost is reduced and the conversion rate is improved by different transferases and the temperature and pH environment more suitable for the transferases; adding activated carbon to absorb the by-products of the reaction, so that the obtained filtrate has higher purity.
Compared with the prior art, the invention has the following beneficial effects:
(1) the method improves the content and the conversion rate of the AA-2G product;
(2) the invention simplifies the production process and is beneficial to industrial production.
Drawings
FIG. 1 is a flow chart of the production process of 2-O-alpha-D-glucopyranosyl-L-ascorbic acid.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to limit the practice of the invention.
Example 1
The production method of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid comprises the following steps:
(1) and (3) synthesis reaction: dissolving VC in water of 40 +/-5 ℃, adding a glucose group donor, keeping the temperature, stirring for 30min, adjusting the pH value to 5.0, adding alpha-isomaltose glucosyl sugar forming enzyme, and uniformly stirring to obtain a reaction solution;
raising the temperature of the reaction solution to 48 +/-2 ℃, keeping the temperature for reacting for 40 minutes, stopping heating, reducing the temperature, starting heating when the temperature of the reaction solution is reduced to 28 +/-2 ℃, raising the temperature of the reaction solution to 48 +/-2 ℃, stopping heating, reducing the temperature, repeating the steps in the same way, and reacting for 20 hours to obtain a synthetic solution;
(2) and (3) purification: cooling the temperature of the synthetic solution to 30 +/-5 ℃, adding alpha-amylase, and stirring for 40 min; then adding active carbon, stirring for 30min, and filtering;
purifying the filtrate by using a sulfonic cation exchange resin column with a styrene-divinylbenzene copolymer as a matrix;
(3) and (3) freeze drying: and (3) performing ultrafiltration and nanofiltration on the filtrate obtained in the step (2), then concentrating until the mass content of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid is 50%, freeze-drying, crushing, sieving and subpackaging to obtain the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid. The purity of the product was 99.87% and the yield was 74.6%.
Example 2
The production method of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid comprises the following steps:
(1) and (3) synthesis reaction: dissolving VC in water of 40 +/-5 ℃, adding a glucose group donor, keeping the temperature, stirring for 40min, adjusting the pH value to 5.5, adding cyclodextrin glucanotransferase, and stirring uniformly to obtain a reaction solution;
raising the temperature of the reaction solution to 48 +/-2 ℃, keeping the temperature for reacting for 50 minutes, stopping heating, reducing the temperature, starting heating when the temperature of the reaction solution is reduced to 28 +/-2 ℃, raising the temperature of the reaction solution to 48 +/-2 ℃, stopping heating, reducing the temperature, repeating the steps in the same way, and reacting for 30 hours to obtain a synthetic solution;
(2) and (3) purification: cooling the temperature of the synthetic solution to 30 +/-5 ℃, adding alpha-amylase, and stirring for 50 min; then adding active carbon, stirring for 40min, and filtering;
purifying the filtrate by using a sulfonic cation exchange resin column with a styrene-divinylbenzene copolymer as a matrix;
(3) and (3) freeze drying: and (3) performing ultrafiltration and nanofiltration on the filtrate obtained in the step (2), then concentrating until the mass content of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid is 50%, freeze-drying, crushing, sieving and subpackaging to obtain the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid. The purity of the product was 99.9% and the yield was 75.3%.
Example 3
The production method of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid comprises the following steps:
(1) and (3) synthesis reaction: dissolving VC in water of 40 +/-5 ℃, adding a glucose group donor, keeping the temperature, stirring for 35min, adjusting the pH value to 5.2, adding cyclodextrin glucanotransferase, and stirring uniformly to obtain a reaction solution;
raising the temperature of the reaction solution to 47 +/-2 ℃, keeping the temperature for reacting for 45 minutes, stopping heating, reducing the temperature, starting heating when the temperature of the reaction solution is reduced to 27 +/-2 ℃, raising the temperature of the reaction solution to 47 +/-2 ℃, stopping heating, reducing the temperature, repeating the steps in the same way, and reacting for 25 hours to obtain a synthetic solution;
(2) and (3) purification: cooling the temperature of the synthetic solution to 30 +/-5 ℃, adding alpha-amylase, and stirring for 45 min; then adding active carbon, stirring for 35min, and filtering;
purifying the filtrate by using a sulfonic cation exchange resin column with a styrene-divinylbenzene copolymer as a matrix;
(3) and (3) freeze drying: and (3) performing ultrafiltration and nanofiltration on the filtrate obtained in the step (2), then concentrating until the mass content of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid is 50%, freeze-drying, crushing, sieving and subpackaging to obtain the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid. The purity of the product was 99.92% and the yield was 76%.
Comparative example 1
The production method of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid comprises the following steps:
(1) and (3) synthesis reaction: dissolving VC in water of 40 +/-5 ℃, adding a glucose group donor, keeping the temperature, stirring for 35min, adjusting the pH value to 5.2, adding cyclodextrin glucanotransferase, and stirring uniformly to obtain a reaction solution;
raising the temperature of the reaction solution to 47 +/-2 ℃, keeping the temperature for reacting for 45 minutes, stopping heating, reducing the temperature, starting heating when the temperature of the reaction solution is reduced to 27 +/-2 ℃, raising the temperature of the reaction solution to 47 +/-2 ℃, stopping heating, reducing the temperature, repeating the steps in the same way, and reacting for 25 hours to obtain a synthetic solution;
(2) and (3) purification: cooling the temperature of the synthetic solution to 30 +/-5 ℃, adding alpha-amylase, and stirring for 45 min; then adding active carbon, stirring for 60min, and filtering;
(3) and (3) freeze drying: and (3) performing ultrafiltration and nanofiltration on the filtrate obtained in the step (2), then concentrating until the mass content of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid is 50%, freeze-drying, crushing, sieving and subpackaging to obtain the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid. The purity of the product was 99.8% and the yield was 45%.
By contrast, comparative example 1 was stirred for 60min during purification, and the product obtained without purification with cation exchange resin was less pure than the product obtained by the process of the invention, and the conversion of the product of comparative example 1 was lower.
Of course, the foregoing is only a preferred embodiment of the invention and should not be taken as limiting the scope of the embodiments of the invention. The present invention is not limited to the above examples, and equivalent changes and modifications made by those skilled in the art within the spirit and scope of the present invention should be construed as being included in the scope of the present invention.
Claims (9)
1. A method for producing 2-O-alpha-D-glucopyranosyl-L-ascorbic acid, which is characterized in that: the method comprises the following steps:
(1) and (3) synthesis reaction:
dissolving VC in water, adding a glucose group donor, keeping the temperature and stirring, adjusting the pH value to 5.0-5.5, adding glycosyltransferase, and stirring to obtain a reaction solution;
raising the temperature of the reaction solution to 45-50 ℃, keeping the temperature for reacting for 40-50 minutes, stopping heating, reducing the temperature, starting heating when the temperature of the reaction solution is reduced to 25-30 ℃, raising the temperature of the reaction solution to 45-50 ℃, stopping heating, reducing the temperature, repeating the steps, and reacting for 20-30 hours to obtain a synthetic solution;
(2) and (3) purification:
cooling the temperature of the synthetic liquid to 25-35 ℃, adding alpha-amylase, and stirring; then adding active carbon, stirring and filtering;
purifying the filtrate by a strong acid cation exchange resin column;
(3) and (3) freeze drying:
and (3) performing ultrafiltration and nanofiltration on the filtrate obtained in the step (2), then concentrating, freeze-drying, crushing, sieving and subpackaging to obtain the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid.
2. The process for producing 2-O- α -D-glucopyranosyl-L-ascorbic acid according to claim 1, characterized in that: the glycosyltransferase is an alpha-isomaltosylglucosaccharide forming enzyme and/or a cyclomaltodextrin glucanotransferase.
3. The process for producing 2-O- α -D-glucopyranosyl-L-ascorbic acid according to claim 1, characterized in that: the strong-acid cation exchange resin is sulfonic cation exchange resin with styrene-divinylbenzene copolymer as matrix.
4. The process for producing 2-O- α -D-glucopyranosyl-L-ascorbic acid according to claim 1, characterized in that: the mass ratio of VC, water, glucose donor and glycosyltransferase is 1-1.2: 80-100: 0.8-1.1: 0.5-0.8.
5. The process for producing 2-O- α -D-glucopyranosyl-L-ascorbic acid according to claim 1, characterized in that: and (1) adding VC into water with the temperature of 35-45 ℃ for dissolution.
6. The process for producing 2-O- α -D-glucopyranosyl-L-ascorbic acid according to claim 1, characterized in that: adding a glucose group donor in the step (1), keeping the temperature and stirring for 30-40 min.
7. The process for producing 2-O- α -D-glucopyranosyl-L-ascorbic acid according to claim 1, characterized in that: adding alpha-amylase in the step (2), and stirring for 40-50 min; adding active carbon, and stirring for 30-40 min.
8. The process for producing 2-O- α -D-glucopyranosyl-L-ascorbic acid according to claim 1, characterized in that: in the step (3), the mixture is concentrated until the mass content of the 2-O-alpha-D-glucopyranosyl-L-ascorbic acid is 50 percent.
9. The process for producing 2-O- α -D-glucopyranosyl-L-ascorbic acid according to claim 1, characterized in that: in the step (3), the flow rate is 1.5-3 cm/s during purification.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110098548.4A CN112921061A (en) | 2021-01-25 | 2021-01-25 | Method for producing 2-O-alpha-D-glucopyranosyl-L-ascorbic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110098548.4A CN112921061A (en) | 2021-01-25 | 2021-01-25 | Method for producing 2-O-alpha-D-glucopyranosyl-L-ascorbic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112921061A true CN112921061A (en) | 2021-06-08 |
Family
ID=76167586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110098548.4A Pending CN112921061A (en) | 2021-01-25 | 2021-01-25 | Method for producing 2-O-alpha-D-glucopyranosyl-L-ascorbic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112921061A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117106838A (en) * | 2023-08-24 | 2023-11-24 | 安徽天寅生物技术有限公司 | Preparation process of L-ascorbyl glucoside |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060216792A1 (en) * | 2002-08-06 | 2006-09-28 | Kazuhisa Mukai | Process for producing 2-0-alpha-d-glucopyranosyl-l-ascorbic acid |
| CN106220696A (en) * | 2011-03-07 | 2016-12-14 | 株式会社林原 | The manufacture method of the powder containing 2 O α D glucosyl group L ascorbic acid anhydrous crystals |
| CN109295134A (en) * | 2018-09-27 | 2019-02-01 | 安徽天寅生物技术有限公司 | A kind of production method of high-content, high yield L-AA glucoside |
-
2021
- 2021-01-25 CN CN202110098548.4A patent/CN112921061A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060216792A1 (en) * | 2002-08-06 | 2006-09-28 | Kazuhisa Mukai | Process for producing 2-0-alpha-d-glucopyranosyl-l-ascorbic acid |
| CN106220696A (en) * | 2011-03-07 | 2016-12-14 | 株式会社林原 | The manufacture method of the powder containing 2 O α D glucosyl group L ascorbic acid anhydrous crystals |
| CN109295134A (en) * | 2018-09-27 | 2019-02-01 | 安徽天寅生物技术有限公司 | A kind of production method of high-content, high yield L-AA glucoside |
Non-Patent Citations (2)
| Title |
|---|
| YIN-CHU CHENG等: "Preparation and characterization of 2-o-alpha-D-glucopyranosyl-L-ascorbic acid inclusion compound", 《MODERN FOOD SCIENCE AND TECHNOLOGY》 * |
| 王冰等: "维生素 Ｃ葡萄糖苷的研究现状及发展前景", 《生物加工过程》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117106838A (en) * | 2023-08-24 | 2023-11-24 | 安徽天寅生物技术有限公司 | Preparation process of L-ascorbyl glucoside |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6436678B2 (en) | High purity maltose process and products | |
| UA126434C2 (en) | Enzymatic synthesis of d-tagatose | |
| US5462864A (en) | Manufacturing method of high purity maltose and its reduced product | |
| US6346400B1 (en) | Process for the preparation of a maltose-rich syrup | |
| CN104789620B (en) | A kind of method of glucoside ascorbic acid preparation | |
| KR100498758B1 (en) | How to make syrup rich in maltose | |
| WO2019136916A1 (en) | Method for preparing glucose-based stevioside in enzymatic variable temperature and high throughput | |
| CN108707634A (en) | A kind of method and its application of multienzyme coupling production trehalose | |
| CN109295134A (en) | A kind of production method of high-content, high yield L-AA glucoside | |
| CN112921061A (en) | Method for producing 2-O-alpha-D-glucopyranosyl-L-ascorbic acid | |
| CN110734945A (en) | method for synthesizing L-ascorbic acid-2-glucoside | |
| US11549133B2 (en) | Preparation method of amylodextrin | |
| CN109055461B (en) | Production method of isomaltooligosaccharide | |
| KR101105391B1 (en) | Food composition comprising enzymatic hydrolysates of kudzu root and preparation method thereof | |
| JPH0331294A (en) | New oligosaccharide and production thereof | |
| CN112111542A (en) | Preparation method of high-purity isomaltooligosaccharide co-produced resistant dextrin | |
| JP3365644B2 (en) | α-D-Glycosyl kasugamycin, process for producing the same, and antibacterial agent containing the same | |
| CN115975067B (en) | Method for preparing polydextrose by taking glucose mother liquor as raw material | |
| CN112592374A (en) | Preparation method of 6-O-palmitoyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acid | |
| CN110776535A (en) | Preparation method of disodium xanthate | |
| CN111394408B (en) | Panose and production method thereof | |
| JPS61212296A (en) | Production of branched oligosaccharide syrup | |
| JPH04158795A (en) | Production of high-purity maltose | |
| CN108486193A (en) | A kind of method of purification of vitamin C glucoside | |
| JP3062264B2 (en) | Method for producing high purity maltose aqueous solution |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210608 |
|
| RJ01 | Rejection of invention patent application after publication |